Category: virgins

Pool Party

Tammy and I were hanging out at Steph’s house late one afternoon, as we often do. Steph’s parents have a big two-story house only a couple blocks from campus, and it’s a nice place to escape the dorm scene for awhile. We were lounging in Steph’s bedroom, drinking coke and sharing some gossip.

Steph mentioned that her parents were going away on vacation next week. Tammy, who never misses an opportunity, blurted out, “You are so lucky—you get the whole place to yourself, to do whatever you like. Party week!”

Steph licked her lips and said, “Oh come on, like I’m gonna turn the place into a frat house or something!”

I chimed in. “You know, I could sure use some serious recreation right now. It’s summer time, and we’re not even really enjoying it. Summer session really bums me out sometimes. I haven’t even had a date in months.”

Tammy chortled. “That’s nothing, Ann, or little miss Stephanie here’s never had a date at all!” She tugged playfully on Steph’s bare leg, causing her to tumble backwards onto the bed.

“You’re such a liar!” screamed Steph in mock anger. “I have too had a date!”

“You uncle Bubba doesn’t count.”

“Greg and I went out lots in high school. But after he hooked up with Jen, I just got disgusted. Figured I had better things to do with my time.” Steph’s face wasn’t showing much emotion, it was clear she’d gotten used to talking about the breakup with detachment.

“But don’t you get horny?” I asked. Steph blushed. “Sorry,” I quickly added. “I didn’t mean to get too personal.”

“It’s OK,” said Steph. “I just usually don’t talk about things like that. But it’s OK. I fantasize sometimes, but that’s it.”

“Come on! Tell us! Tell us!” Tammy was now on the bed next to Steph, prodding her in the side. Tammy was one of those active, healthy-looking people that make the rest of us feel inadequate—smooth-skinned, toned, proportioned. Steph is small and delicate, with short dark hair and a kind of little-kid look. I could tell she was uncomfortable with Tammy’s rough-housing, but didn’t want to seem uptight, so she put up with it.

“Not much to tell, really. Mostly I fantasize about getting guys turned on . . . strangers, usually, but sometimes guys I know from class. You know, flirting, getting them worked up, maybe flashing some skin. It’s not really about the guys, it’s more thinking about myself acting sexy, that’s the turn-on.”

“And how far does it go?” I asked her.

“Well, sometimes I imagine it going on to sex, but usually I get off before then.” Steph blushed again.

“I have those kinds of fantasies too,” I confessed. “I know guys look at me a lot, and sometimes I’d really like to cut lose and play it up, you know. But then you realize everybody knows everybody, people will start to talk, and all that.”

“That’s the great thing about spring break,” said Tammy, “you’re a zillion miles away, and you know you’re not ever going to see these people again, so you can be uninhibited. I started flirting with this guy on the beach, and two hours later we were screwing in my motel room.”

“You and your stories!” groaned Steph, but I was pretty sure it was true.

“How was it?” I asked.

“It was great,” Tammy went on. “Even though it was just casual sex, he was really very affectionate. And the fact that he was someone I barely knew made it really exciting, not the predictable kind of thing you can get into with a boyfriend you see every week.”

“Maybe—gee I don’t know—is there any way we could indulge ourselves a little?” I was speaking slowly, and looking for the right words. “Have a party here, like Tammy suggested, and invite just a few guys, and have fun getting them turned on.”

“That could get way out of hand in a hurry,” muttered Steph.

“I’m game!” announced Tammy, predictably. “Maybe we could swear them to secrecy or something.”

“That never works,” I sighed. I felt confused. Somehow making such a specific suggestion made the possibility seem real, and exciting, and my mind couldn’t stay away from the idea, even though it was really no different from going to class dressed like sluts.

“Some guys don’t like gossip,” suggested Steph. I was surprised to see her start to take this seriously. “This guy in my anthropology class is really cool. I’ve never heard him disrespect anybody.”

“Yeah, but that type runs away if you start to flirt!” Tammy laughed.

“No, no, he’s not like that. I’ve seen him checking out girls and trying to make conversation. He’s really nice.”

“What’s his name?” I asked.

“Rich,” she said. And with that we were on our way. The “guest list” started to fall into place. We ended up with five names, all suggested by Steph and I. (It seems Tammy didn’t know any well-behaved guys.)

I noticed it was after eight already. “I need to go,” I said, and got up.

“Just a minute,” said Steph. “I want to get clear about what we’re actually doing here. Just how sexy are we going to get? It’s not going to be some kind of orgy, is it?”

Tammy and I giggled. “No,” I said with friendly reassurance. “It’s just a game. See how hot we can get them, but we stay cool and act like nothing special’s up. We just let them have a taste of our sexy sides.”

“How much of our sexy sides?” asked Steph with a serious expression.

Tammy couldn’t keep quiet any longer. “Look, guys, this is supposed to be fun—the whole point is to get a little uninhibited, do something spontaneous for once. We just see how it goes, OK? We’ll have the party out in the backyard, by the pool, so we’ll have an excuse for showing some skin. That right there is enough to make any guy horny. Stop biting your nails and just go for it!”

That seemed to be the final word on the subject, so I went back to the dorm and worked on my algebra homework before bed. The next day, we met in the park at lunch and set a date for the party, and went over the guest list again. We decided who would bring wine and snacks. We also agreed we would wear our sexiest swimsuits.

Only one of the guys said he couldn’t make it. The other four seemed pleased to have a female acquaintance invite them to a pool party, but since neither Steph or I are known for partying, they probably didn’t expect much.

The night before the party, I tried on the three swimsuits I owned. I didn’t feel very sexy in any of them. Hesitating—it seemed a dangerous decision, somehow—I decided to go buy a new one. There’s a little shop off campus that sells skimpy swimsuits, party wear, and the like. I found a little black suit with string straps and a thong bottom. Just trying it on in the dressing room made my whole body tingle. It made my fair skin look like alabaster, and made my wavy dark hair look like it was actually part of a “look,” for once. And just the sensation of air on the delicate skin of my butt was a turn-on. I wasn’t really sure I could go through with this. I got a nice green sarong to wrap around over the thong, so I could decide what to do on the spur of the moment. That was Tammy’s approach, after all, and she seemed to know what she was talking about.

We got together at Steph’s about an hour before the party was supposed to start. Steph was already in her suit, an athletic-looking thing that really fit her well. With clothes on, she didn’t appear to have much of a figure, but in the suit you could see that her body, although small and slim, was not at all boyish. She had soft, round curves and very smooth skin. Tammy went into the bathroom to change. I used Steph’s room. Tammy came out in a hot pink bikini, with one of those cut-off T-shirts on top. I noticed her skin was almost the same deep golden-brown color as her hair. She either sunbathes a lot or goes to one of those tanning salons. Both of them said my sarong was really stylish. It was, actually. Very sensual, but I didn’t feel at all cheap wearing it.

Rich arrived first. He was taller and cuter than I had thought from hearing Step talk about him. Short blond hair, a gentle smile, and a surprisingly deep voice. Then came Mark, a friend of my physics lab partner; I’d even had lunch with him a couple times. He was shorter than Rich, and wore a neatly trimmed beard that made him look several years older. Steph volunteered to stay by the door while Tammy and I went out to the pool with our guests. We served wine, put the cheese and crackers out, and for a while just sat around on the pool furniture and lawn, getting a little better acquainted. Tammy was on the lawn, and from time to time coyly rearranged herself, sliding her long tans legs around and running her hands down them absent-mindedly. I was on the lawn chair, and being very casual about how my sarong fell and how much leg it showed.

About ten minutes later, Steph joined us with John and Carlos in tow—she was actually holding both their hands as she walked out through the sliding glass door toward the pool. John was a bit heavy, but one of those instantly likeable people, always ready to extend a smile or a hug or make a friendly remark. Carlos was very slender, with wavy black hair and large eyes. I’d never known him to speak much, but he was an art major, and I’d seen some of his sketches—good stuff, really—strangely moving nude figures juxtaposed with colored geometrical forms.

I got off the lawn chair and settled down on the grass, very close to Mark. I made sure our arms were brushing against each other, touching. The sort of little move that says, “if being close makes you uncomfortable, you can back away—but it doesn’t bother me.” Mark stayed pleasantly close, and even put the arm he was leaning on a bit further behind my back, where I could feel his thumb and wrist, just barely grazing my bottom.

Tammy, of course, was a couple steps ahead of me. She had one of her beautiful bare legs draped casually over Rich’s knees, telling him some sort of joke, but with her voice just soft enough to convey that the conversation was for him, not the rest of us. Steph was trying to attend to both the latecomers at the same time. She was listening to John, who was being talkative, but she still had her fingers on Carlos’s hand, moving them slightly from time to time.

Mark said, “You look great. Do you work out?”

“Thank you,” I said. “No, not much, but I swim and go to the spa.”

“The spa?” he asked.

“Yes, they give great massages—and if you go when the student masseuses are there, it’s not expensive at all.”

“It doesn’t bother you to get undressed?” he asked. And I could tell that saying it was making him visualize it.

“No,” I said. “It’s professional, you know. It just feels great to be touched all over, very relaxing, almost like a nap.”

Our little conversation was suddenly interrupted by Tammy, who now raised her voice for everyone to pay attention. “This is a pool party—you guys brought swim suits, didn’t you?” Rich and John said they had, and Steph led them back into the house to show them where they could change. Mark said he didn’t bring his, and Carlos said he didn’t swim. Mark did take off his sandals and shirt, though, leaving him wearing only his shorts, and still very close to me. I rested my hand on one of his legs, and he returned the favor, but his hand moved back and forth in a kind of circular motion. It felt wonderful.

John and Rich returned in their swimsuits. John went straight to the pool and dove in. Rich returned to sit next to Tammy again. She stood up, pulling him up with her. “Come on!” she said eagerly, “let’s go in the water!” With that, she lifted her short T-shirt off over her head, and there was no swimsuit top underneath. I was startled—I had just assumed she had a top on under the shirt. All the men’s eyes turned, as she strutted slowly to the edge of the pool, dressed only in her hot pink bikini briefs, and dove in. Rich was right behind her. John, perhaps feeling a bit uncomfortable, climbed out of the pool and lied down on the grass, next to Mark and I.

“God!” whispered Mark, his voice catching in his throat. “She is hot.”

“Getting turned on?” I asked, with a joking lilt in my voice, but I ran my hand all the way up his thigh, partway under the leg of his shorts. He didn’t answer, but his hand went around my waist, and then moved down, one or two fingers slipping inside the top of my sarong as he massaged the small of my back. I glanced over at Steph. She was holding Carlos’s hand close to her face, kissing his fingers. Tammy’s going topless seemed to have got things moving…much faster than I had anticipated. I watched Tammy and Rich playing in the pool. It was hard to see what they were doing, but there was sure a lot touching going on. Mark, meanwhile, was getting braver with his hand, plunging it deep under my sarong and massaging the cheeks of my ass, as well as he could reach with me still sitting on the ground. I nested my head against his neck and kissed him there, sensuously, a couple times. Then I got up, whispering softly, “Let me get this off.” I slipped the sarong off my hips and settled into his lap. We started kissing, and now his hands were caressing my breasts. I knew now that this party wasn’t going to be a flirtation game. I was already too turned on to keep that kind of control.

Just when I was loosing myself in the embrace, Tammy and Rich appeared, standing in front of us, thoroughly wet. Rich had a very obvious erection, and Tammy was fondling it, through his dripping swim shorts. “You guys having fun yet?” Tammy asked. I managed to smile. She whispered something in Rich’s ear, and the two walked across the lawn. Tammy knew how to get attention, even with two other couples starting to make out. She swung her hips as she walked away from us, her damp swimsuit bottoms clinging to her ass. Mark and I repositioned ourselves to watch the two of them.

They got to the far corner of the lawn, and we could see them standing there, tongue-kissing and groping each other. His hands were all over her naked breasts, kneading and grasping and rubbing. She was running her hands up and down his back, desperately. Then her hands plunged into his shorts, massaging his buns. After one or two caresses, she suddenly pulled his shorts down to his feet. He stepped out of them, naked, and she turned him halfway around so that everyone could see his thick hard erection.

“They’re gonna fuck!” said Mark, panting. I shifted my position on his lap so that I was straddling him, one leg on either side, but our eyes were glued on Tammy and Rich. Rich was on his back now, and Tammy was giving him head. After every few sucks, she would take his cock out her mouth and stretch the skin with her hand, glancing up to make sure the rest of were catching on. We were. Mark and I were practically humping each other through our clothes. John was lying beside us, naked now, and jacking himself off. I glanced over at Steph just in time to see Carlos stand up and drop his pants, right in front of her face.

We watched as Tammy stood up and pulled her suit bottoms off. For a moment, she stood over him. It looked like she was touching herself. Then she bent down, clasped Rich’s cock in her hand, and slid it up her cunt as she straddled him. Even from across the lawn, we could hear her moaning as they fucked. Her sensuous, tanned bodied writhed and turned. Sometimes she would rise up until he was almost completely out of her, and then plunge back down with a loud moan.

Mark was tugging at my thong now, desperately trying to grope my pussy as I was grinding it into his shorts. “I need to fuck you,” he whimpered, almost crying.

“Do it,” I said, hardly able to catch my breath. I stood up, pulled my thong off, and got down on my hands and knees. A moment later, Mark was behind me. I was so wet that the penetration was amazingly slippery: in one quick plunge he was deep inside me. His vigor was amazing. I’d only had sex with a couple men before, and it had always been indoors, in a romantic context, where things happened gradually. But this was different. It was just insatiable lust. And it was good. His strokes were fast and deep, and he was so hard that I felt completely at his mercy. My hips moved in response to his, and I ground my ass into his body with every thrust, loving the feel of his strong pelvis pressed against my cheeks. I no longer knew or cared what anyone else was doing.

I felt an orgasm building up, and then it was suddenly there, and I was squirming, arching my back, choking a cry. Still he kept fucking me, even harder now. I felt like a wild animal. Then another one. This time, I screamed, completely lost, forgetting I was in the backyard of a suburban neighborhood. Mark grabbed my waist with such force that I knew I would have bruises the next morning. With all his strength, he shoved my ass back against him, at the same time plunging his cock in as deep as he possibly could and let lose a great gush of come. He collapsed, and I collapsed with him, onto the cool grass, with the afternoon sunlight beaming down on us and the open air moving just slightly, caressing our limp and drained bodies.

It was some time before I even opened my eyes again. Mark and I staggered to our feet and looked around. Everybody was totally naked. Tammy and Eric were pouring themselves more wine, laughing, and holding each other in a playful, cuddly kind of way. And Steph…I did a double take, to be sure what I was seeing. She was in the middle of the lawn, going at it with John and Carlos, sandwiched between them. John was on the bottom, with his cock up her cunt, and Carlos was on top, fucking her asshole from behind. They were all panting and heaving.

I got a sudden memory of her intense little voice, asking, “How much of our sexy sides?” and I smirked and plunged into the pool. It was good to cool off.

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First Time Anal By The Pool

It was a hot day and as soon as I could finish work I headed home with the intention of having some cold drinks and lazing round the pool. I’m in my early 40s (OK, 44) and live alone with my 18 year old daughter, Suzie. My divorce was settled recently and I’ve got no plans other than seeing Suzie through university and living a comfortable uncomplicated life.

I had just changed into swimming briefs and was pouring a scotch over a tumbler of ice when the doorbell rang. It was Jamie, one of Suzie’s friends from school days, who lives nearby. Suzie doesn’t have much time for her, and they share little in common, but Jamie doesn’t know when she’s not wanted. She hadn’t been around for a couple of weeks – not since a row caused by her trying to race off Suzie’s boyfriend (frankly, in my view, Jamie could have the worthless prick). But I suppose it was too much to hope that she’d stay away for long.

Today she was in high heel clogs, white hot pants and pink halter top, the ring in her belly button on display as well as her recently bleached hair with pink streaks, pink nails, and overkill makeup. ‘Hi Mr. D!’ she said, in a voice overly cheery to hide her insecurity. ‘Is Suzie at home?’ Jamie has long been a regular visitor, using our place as a refuge since she first started getting in trouble with her folks about four years ago – smoking, underage drinking, truancy, unsavoury boyfriends, drugs.

‘Sorry, Jamie, she’s got a couple of late lectures and is staying over at her mother’s place.’

I moved to close the door, but Jamie piped up again. ‘I was just hoping to chill out by the pool for a while, you know, ‘cos things are a bit tight at home just now.’ I raised an eyebrow and she went on. ‘I dropped out of TAFE yesterday – again! tee hee – and went round to Jay’s and got ripped and the olds are real pissed.’

I have trouble keeping up with Jamie’s misadventures. Having dropped out of school in year 11 her parents enrolled her for secretarial school. That lasted a few months then they got her into a vocational college for animal handling, but she dropped out of that. I think the last one was jewellery making or some such. As for Jay, he’s the latest loser in a string of doped up, dropped out, pasty-faced, hollow-eyed wasters that she’s hung out with.

I really wanted to be on my own but shrugged OK and she walked by me heading for the patio door, tottering on her clogs. I finished fixing my drink and debated whether I should change out of my skimpy briefs and into something more modest. But what the hell. Jamie had seen me round the pool in these togs and the shorts didn’t exactly reduce my gut or anything. I went outside, she was sitting on a lounge in a skimpy pink bikini, sunglasses perched on top of her head, applying sun cream to her legs. I sat and watched her as I sipped. Her skin was quite pale – despite having spent half the summer over here – and smooth. She was still quite adolescent in shape, a bit of puppy fat, smallish breasts, but shapely legs and her butt filled out her bikini nicely. Very nicely.

(more…)

First Time Anal By The Pool

It was a hot day and as soon as I could finish work I headed home with the intention of having some cold drinks and lazing round the pool. I’m in my early 40s (OK, 44) and live alone with my 18 year old daughter, Suzie. My divorce was settled recently and I’ve got no plans other than seeing Suzie through university and living a comfortable uncomplicated life.

I had just changed into swimming briefs and was pouring a scotch over a tumbler of ice when the doorbell rang. It was Jamie, one of Suzie’s friends from school days, who lives nearby. Suzie doesn’t have much time for her, and they share little in common, but Jamie doesn’t know when she’s not wanted. She hadn’t been around for a couple of weeks – not since a row caused by her trying to race off Suzie’s boyfriend (frankly, in my view, Jamie could have the worthless prick). But I suppose it was too much to hope that she’d stay away for long.

Today she was in high heel clogs, white hot pants and pink halter top, the ring in her belly button on display as well as her recently bleached hair with pink streaks, pink nails, and overkill makeup. ‘Hi Mr. D!’ she said, in a voice overly cheery to hide her insecurity. ‘Is Suzie at home?’ Jamie has long been a regular visitor, using our place as a refuge since she first started getting in trouble with her folks about four years ago – smoking, underage drinking, truancy, unsavoury boyfriends, drugs.

‘Sorry, Jamie, she’s got a couple of late lectures and is staying over at her mother’s place.’

I moved to close the door, but Jamie piped up again. ‘I was just hoping to chill out by the pool for a while, you know, ‘cos things are a bit tight at home just now.’ I raised an eyebrow and she went on. ‘I dropped out of TAFE yesterday – again! tee hee – and went round to Jay’s and got ripped and the olds are real pissed.’

I have trouble keeping up with Jamie’s misadventures. Having dropped out of school in year 11 her parents enrolled her for secretarial school. That lasted a few months then they got her into a vocational college for animal handling, but she dropped out of that. I think the last one was jewellery making or some such. As for Jay, he’s the latest loser in a string of doped up, dropped out, pasty-faced, hollow-eyed wasters that she’s hung out with.

I really wanted to be on my own but shrugged OK and she walked by me heading for the patio door, tottering on her clogs. I finished fixing my drink and debated whether I should change out of my skimpy briefs and into something more modest. But what the hell. Jamie had seen me round the pool in these togs and the shorts didn’t exactly reduce my gut or anything. I went outside, she was sitting on a lounge in a skimpy pink bikini, sunglasses perched on top of her head, applying sun cream to her legs. I sat and watched her as I sipped. Her skin was quite pale – despite having spent half the summer over here – and smooth. She was still quite adolescent in shape, a bit of puppy fat, smallish breasts, but shapely legs and her butt filled out her bikini nicely. Very nicely.

I finished my drink and got up for a second. ‘Wanna beer, Jamie?’

‘Uh, no thanks Mr D, I don’t really like beer.’ I shrugged. ‘But I’d love a vodka and orange!’ I shrugged again and headed inside. I fixed a more moderate scotch for myself, then the drink for Jamie, heavy on the vodka. She looked quite the try-hard wannabe sophisticate – lying back on the lounge, sunglasses, cigarette, cocktail. I chuckled inwardly and resumed my seat. It was good for a guy’s ego to have a pretty young thing almost naked about the place. I was conscious of her checking me out from behind her dark glasses and hoped I didn’t look too unattractive. I guess I’m carrying a bit more weight than I should, but my gut is smaller than most men my age, and it’s covered with a summer tan and a matt of brown hair that my wife always liked. And my arms and chest are still shapely enough from all the years of swimming. So all is all, I didn’t mind Jamie’s scrutiny, and anyway she’d been doing it all summer, even flirting with me when Suzie wasn’t around.

Jamie prattled on a bit about how boring her course had been, about music and so on. I didn’t need to contribute much more than a grunt every now and then. I swam a few laps and Jamie followed me into the pool, splashing about and making girly noises. I paused after ten laps and Jamie was sitting on the edge of the pool waiting for me to surface. Her open legs were inches from my nose and she giggled as she saw me staring at the tight fabric outlining her vulva. I had half a mind to tell the cock teaser to go home, but decided to splash her instead. She shrieked artificially and jumped in on top of me. We horsed around and she managed to press her tits against me several times and grope my butt and groin. I climbed out and dozed for a few minutes in the waning sun, while Jamie fussed with lotions and cigarettes. I took our glasses in for a top-up. When I returned, Jamie took her glass, had a gulp (not seeming to notice that it was almost a third vodka) then rolled onto her front and asked me to put tanning lotion on her back. I said the sun was so low that she didn’t need to worry and she tossed the hair out of her eyes and gave me a pouty look. I enjoy a bit of flirting and gave her a knowing grin.

‘So, like anyway,’ she said, ‘you haven’t said how you like my new tattoo.’ She had a dark blue celtic pattern in a swathe across the small of her back with a loopy arrow head in the middle pointing downward, its tip disappearing below her bikini line. It’s the kind of tattoo you see on women hanging around in malls and city corners. I had been kind of marvelling at it when she was splashing about in the pool. Jamie sure has a fierce instinct for downward mobility.

‘Well?’ she demanded, wriggling her butt in case I wasn’t looking hard enough.

‘I can’t see all of it, but I guess I like better where it’s pointing,’ I said, grinning again.

‘Mr D!’ she screeched in mock outrage, delighted that I was playing along.

We both took a slug from our drinks. I hunched forward and said, ‘So, are you going to show me all of it?’

‘Uh huh,’ she replied all bright eyed. She reached back and inched the hem of her bikini halfway down her butt. I was more interested in the yummy butt crack and swell of her pale cheeks, than the final swirl of the tattoo. She was watching me, mouth slightly parted, as she held her bikini down – longer than was necessary – then inched it even lower.

I got up and walked the three paces over to her lounge, then crouched down beside her. I ran my hand over her lower back, tracing the edges of the tattoo, then following it down to the parting of her buttocks. ‘It doesn’t do you justice,’ I murmured, massaging the firm mounds. Her eyes had widened and she was panting – nervousness? anticipation? I continued to massage her butt, nudged her hands away and pushed the bikini bottom further down, revealing the full glory of her 18 year old bum. I massaged it in a full round motion, managing to graze her perineum with my fingertips and trailing my thumbs through her humid cleft. I paused and nudged her thighs. She was quick to spread them wider and now I was able to touch her labia as I massaged.

‘You like that, Jamie?

‘Yes, Mr D.’

‘Do you want me to stop?’

‘No, Mr D.’

I kept up the massage, Jamie sighing as my fingers played with her bottom and labia. After a minute I tugged her bikini bottom al the way down and tossed it on the ground. Kneeling behind her, I pushed her legs wide and pulled her butt back and up so she was slightly on her knees. God it was a magnificent sight! Pink labia slightly damp from arousal, fringed with curly blond hair, a tantalising little path back between bulging flesh to a dainty little purply-brown crinkle. I leant forward and teased the labia open with the tip of my tongue. Jamie tensed and then gasped when I sought out her little clit hood, washed around it then swiped back deep between her labia. She tasted fresh and sweet and after a couple of moments her little bud had emerged from its sheath. I lapped on the clit making Jamie sigh and arch, then plunged my tongue back into her slick vagina. She was getting very wet and I delved deep for her juices between licking the now-straining clit. But it was her arse I wanted and it was time I paid it the attention it deserved. I made a long swipe up from her vagina to her anus, washed round the pucker and probed at its centre.

‘Jesus, Mr D!’ Jamie gasped. ‘What are you doing?’

By way of reply, I put my hands more firmly on each buttock and held them wide apart, pushing harder with my tongue. We both grunted when the muscle gave way. I reamed, Jamie moaned and we discovered that we were doing something we both very much liked. I got a finger on her clit and stroked it to the rhythm of my tongue. It was a technique I’d developed with my ex-wife guaranteed to bring her off and get her compliant for a solid buggering. It was a few years since I’d had an opportunity to use it and was glad to see it was working well on someone else. And Jamie tasted better than my ex – less earthy, less sour and less sharp. I dug deep, searching for that hot rectum flavour, and Jamie moaned in response. With my ex, this kind of action soon brought her off, but it was taking much longer with Jamie and my jaw was beginning to tire. I eased back on the clit action and slid the middle finger of my other hand into her oh so tight twat. She gasped when I found her g-spot and started up a steady moaning as I rubbed the velvety pad. She was getting close and I ate her arse with renewed vigour, maintaining the clit and g-spot diddling. Her bung hole was gaping, my tongue was jabbing deep in the fetid passage, saliva and arse butter were dripping down my chin, my fingers were slipping over her buttons. When she came it was with a wrenching heave that dislodged my face. I let her slump forward on to the lounge, my fingers coming free. Her mouth was open in a soundless scream, eyes shut and hands grasping at the lounge legs. Her pert butt was all splotched from my hands and as she writhed I could see her anus all glistening and pulsing. I couldn’t resist the temptation and bent forward. Jamie gasped and moaned afresh when I held her buttocks apart and sucked on the pulpy ring, still twitching from her orgasm. Her sphincter weakly gripped my tongue as she went through the dying throes, then her arse went slack. I gave it a good workout, pumping lots of saliva in for the action that was still to come.

I sat back on my haunches, my cock pushing out the front of my swimming briefs. Jamie looked back at me, her face flushed and lips moist. ‘Jesus, that was awesome,’ she said a little breathlessly. I smiled, leant forward and kissed her hard, letting her taste her arse on my lips and tongue. She didn’t seem the least averse as her tongue swirled against mine. For my part I got the unfamiliar taste of tobacco.

‘That good?’ I asked sitting back again.

‘A real first,’ she nodded, eyes all misty.

‘Never been rimmed before?’ I grinned.

‘Not that either,’ she said. ‘But I meant my first orgasm.’

‘You’re kidding!’ I said. ‘Never cum before?’ She shook her head. ‘How long have you been having sex?’

‘Uh, nearly four years, I guess. But it’s never been like this.’

Christ! I thought, wondering briefly about what kind of sex life she’d been leading, then mentally shrugged. There were more immediate concerns. ‘Well, you’re in for some wonderful times. But right now it’s time to return the favour,’ I said standing and moving so that my bulging trunks were before her eyes. She looked at the stretched fabric and the tip of her tongue wet her lips. ‘Suck me!’ I hissed, pulling up the left leg of my bathers and easing out my boner. Jamie sat up and engulfed the first half of my cock. She started a sloppy blow job, but wasn’t handling it too well. Clearly no-one had ever taught the kid to suck dick. After her teeth had grated against my glans a couple of times, and my pole had been almost bent in half against her jaw, I figured I was in danger of injury. So I pulled out and told her to suck my balls. With just a couple of directions she was doing a great job, tugging each one out in turn and sucking on it hard enough to make my cock twitch and knees buckle. It’s something that has always made my jizz rise, but my ex was always grudging about doing it, saying my balls were too hairy. But Jamie seemed eager enough so I let her do it for a nice long time.

‘Now I’m ready to fuck that beautiful arse,’ I said, tugging a reddened testicle from between her plump lips. She looked taken aback and I thought for a moment. ‘You have been butt fucked before, haven’t you?’

‘Uh uh,’ she shook her head. Christ! An anal virgin! My cock twitched and jizz boiled.

‘Well, it’s a day for firsts!’ I replied.

‘Won’t it hurt?’

‘Naahhh,’ I reassured her. ‘The secret for enjoyable anal sex is firstly lots of preparation – and honey there ain’t better preparation than being reamed out for 20 minutes! – and secondly, lubrication.’ I smiled and she looked less uncertain. I reached to her bag and took out the after sun lotion I could see there, and held it up. ‘And this will do just fine.’

‘But you’re so big,’ she said in a worried voice.

What the…? I’m not any bigger than average, just your regulation six and a half inches. Again I wondered what her sex life had been like. I just gave her a calm smile and directed her to go up on her hands and knees.

Once she’d assumed the position, I stood behind her and straddled the lounge, my feet on either side. It was low enough to the ground that I could fuck her like that and I applied lots of lotion, first to my cock and then to her butt. I was pleased to see that despite all the tonguing it had closed nicely and was back to its virginal tightness. I then shuffled forward and fitted my bulging cock head to the little glistening pucker. ‘Remember how good it felt when I was licking you?

‘Uh huh,’ she said a little uncertainly.

‘Well, this is going to feel even better.’ I pressed forward and after a moment her greasy sphincter gave way under the steady pressure. I could feel her ring clenching, but her hole was so well lubed that she couldn’t prevent my entry.

‘Yyaaaggh!’ she gasped as my purple helmet slid through her ring and lodged in her rectum. I paused to let her get used to it. Actually, her pucker was clenched so tight that I was in danger of cumming. Both of us were panting. ‘Take it out!’ she gasped. ‘You’re too big, Mr D!’

‘Hang on kid,’ I said soothingly. ‘It’ll get better in a minute.’ I reached forward and slid a finger in her mouth. She sucked it desperately and I fitted in another then gently fucked them back and forth. After a moment, she was distracted enough that I felt her butt unclench a fraction. I took the opportunity to drive forward and she immediately stiffened and gasped. But I wasn’t going to be denied this time and kept bearing forward until I was all the way in that hot glove like arse, my balls resting against the slimy perineum.

I was in danger of jetting again, right on the verge, and had to hold still. Jamie felt my cock pulsing. ‘Are you cumming?’ she asked in a hopeful whimper.

‘Uh uh, kid.’ I chuckled. ‘But when I do,’ I reassured her, feeling my staying power return, ‘you’re going to know for certain.’ I jagged a couple of fingers back in her mouth, got a fistful of her hair with the other hand and tugged her head back, causing her body to arch delightfully. She was taut as a bowstring. ‘And before then,’ I said, tightening my grip on her hair, ‘you’re going to know what anal sex is all about!’ With that I started some steady deep stroking, just the bottom third of my cock emerging from her pooper before ramming back in. She was going uuunnnhhh! uuunnnhhh! uuunnnhhh! and sucking hard on my fingers. Her arse was loosening up and she was handling the full depth OK. I decided it was time for something more vigorous and began to pound her with full strokes, screwing my hips hard each time I bottomed out. It was such a hot tight arse that I began to lose it a bit and fucked her pretty wildly, driving her down so that she was prone on the lounge, my full weight behind each thrust. After a couple of minutes I realised she was crying around my fingers and eased up a bit.

‘OK honey?’ I asked soothingly.

‘It hurts, Mr D!’ she whimpered.

‘Too dry?’ I asked making a couple of quick rabbit hunches. ‘Or too deep?’ I said driving as far forward as possible and pulling her hair so that she arched and took it that fraction deeper.

‘Please stop,’ she blubbered, and then sucked on my fingers.

I wanted to see her face as I fucked her arse; get off on her emotions. ‘I know what,’ I said. ‘The angle must be wrong.’ I let go her hair and stood back, my cock coming out of her butt and leaving it gaping. I looked for a few seconds until it closed. Then I told Jamie to roll onto her back. She did so and I hitched her ankles high on my shoulders and lifted those separated buttocks up high. She had her bottom lip caught between her teeth and was looking at me with wide apprehensive eyes. I told her to pass me the tube of cocoa butter and applied more of the thick grease to my reddened cock. I then fitted my cock to her date and pressed till it was on the point of giving way. I paused and looked at the kid’s face, wet where my fingers had wiped saliva, hair mussed. I gave her a reassuring smile. ‘Push back at me, honey. It will feel better.’ She did and her crinkle flowered and my cock slid in.

We both groaned and I paused, my cock half way in. ‘Feels good, doesn’t it?’ Her face was strained but she gave me an uncertain nod. I stayed like that and began to kiss and stroke her calves, then her feet. She squirmed when I got to her toes and giggled as I sucked slowly on each one. I don’t know if it turned her on or not, but I could feel her gut relax and gave her another inch of cock. She was smiling now. ‘Ready for some more?’

‘Uh huh,’ she smiled. I sank slowly forward onto her breasts, my cock sinking deep into her bowel. I kissed her hard and she responded hotly. I humped away as I forced her teeth wide, chewed on her tongue and bit her lips. Then I started fucking her harder, brutalising her arse as I brutalised her mouth. The little minx was up for it this time, her tongue duelling with mine, panting hotly with each thrust. I pulled back a bit and panted at her to tug her tits out of the bikini top. Then I was on them like a beggar at a banquet, feasting on the hard little nips and creating a pattern of bite marks on the soft mounds. She was heaving back at me now, trying to grind her clit against my pubic bone as I bore down. I went upright again and rubbed her cunny as I fucked her arse, making her hiss and toss her head. I did her that way for four or five minutes until she came, a fed flush spreading from her neck over her chest as she whimpered and groaned. Her clenching anus reminded me that I wasn’t far off and I gave her a nice stroking as she rode out her orgasm.

She looked up at me with smouldering eyes and pulled me down on her chest again. We kissed and this time it was her who bit and chewed. She was hot and I was close. ‘Do you like the taste of cum?’ I panted, sweat dripping off my forehead onto her splotched chest.

‘Uh, not really,’ she panted back, not realising what I was about to do.

‘Well. I understand it’s an acquired taste,’ I grunted suddenly pulling out of her butt and crouching by her face. I grabbed her hair and pushed my greasy shit streaked tool against those bruised lips. Her eyes flew wide but I jagged forward and into her mouth. She was totally passive, her eyes showing her distaste. I slapped her cheek not so gently and hissed at her to suck. Startled she complied and I groaned as I felt my balls begin to boil. ‘Work my balls!’ I demanded and I felt a hot little hand cup my sac. ‘Yeah, baby!’ I moaned as the double action of mouth and hand worked their magic. She sensed how close I was and started to apply herself with a will. Looking down at that girlie face concentrating on my cock, a fleck of shit caught in the moist corner of her mouth as she bobbed back and forth on my shaft, was enough to bring me off. With a straining jag forward of the hips and a long grunt, my balls emptied. I held her head in place while my cock pulsed and jetted, her gagging sounds making it all the more intense. Finally I was finished. Panting I looked down at Jamie, my hand still wrapped in her hair holding her to my softening cock, a trickle of thick sperm oozing from one corner of her mouth.

‘Swallow,’ I ordered and waited till she’d done so before releasing her and tugging my cock from between those plump lips. Then I knelt beside her and kissed that hot bruised mouth, tasting the remnants of my seed. It took her a few seconds to respond, but when she did, it was with some enthusiasm.

‘So, kid,’ I said, sitting back on my haunches and stroking her thighs. ‘Enjoy that?’

‘Uh, huh,’ she said, eyes sparkling. ‘Maybe not all, but … yeah, I guess all!’

‘Great!’ I smiled back. ‘I’m just going inside to get another drink. You want one?’ When I came back out with the glasses and a cloth to wipe clean the lounge, Jamie was lying back smoking, one hand gently massaging her blotched breasts. I handed her the straight orange juice and watched as she gulped it down. Then I packed her off back home. She whined and carried on wanted to stay knowing that I’d be alone all night, but I didn’t want her to get the wrong idea. It was only sex. She pouted, whined and begged so I told her she could come back the next Thursday when I’d be alone again. Afterall, I reasoned, someone ought to teach the kid how to suck cock. That is, if I could keep away from her arse long enough …..

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First Time Anal By The Pool

It was a hot day and as soon as I could finish work I headed home with the intention of having some cold drinks and lazing round the pool. I’m in my early 40s (OK, 44) and live alone with my 18 year old daughter, Suzie. My divorce was settled recently and I’ve got no plans other than seeing Suzie through university and living a comfortable uncomplicated life.

I had just changed into swimming briefs and was pouring a scotch over a tumbler of ice when the doorbell rang. It was Jamie, one of Suzie’s friends from school days, who lives nearby. Suzie doesn’t have much time for her, and they share little in common, but Jamie doesn’t know when she’s not wanted. She hadn’t been around for a couple of weeks – not since a row caused by her trying to race off Suzie’s boyfriend (frankly, in my view, Jamie could have the worthless prick). But I suppose it was too much to hope that she’d stay away for long.

Today she was in high heel clogs, white hot pants and pink halter top, the ring in her belly button on display as well as her recently bleached hair with pink streaks, pink nails, and overkill makeup. ‘Hi Mr. D!’ she said, in a voice overly cheery to hide her insecurity. ‘Is Suzie at home?’ Jamie has long been a regular visitor, using our place as a refuge since she first started getting in trouble with her folks about four years ago – smoking, underage drinking, truancy, unsavoury boyfriends, drugs.

‘Sorry, Jamie, she’s got a couple of late lectures and is staying over at her mother’s place.’

I moved to close the door, but Jamie piped up again. ‘I was just hoping to chill out by the pool for a while, you know, ‘cos things are a bit tight at home just now.’ I raised an eyebrow and she went on. ‘I dropped out of TAFE yesterday – again! tee hee – and went round to Jay’s and got ripped and the olds are real pissed.’

I have trouble keeping up with Jamie’s misadventures. Having dropped out of school in year 11 her parents enrolled her for secretarial school. That lasted a few months then they got her into a vocational college for animal handling, but she dropped out of that. I think the last one was jewellery making or some such. As for Jay, he’s the latest loser in a string of doped up, dropped out, pasty-faced, hollow-eyed wasters that she’s hung out with.

I really wanted to be on my own but shrugged OK and she walked by me heading for the patio door, tottering on her clogs. I finished fixing my drink and debated whether I should change out of my skimpy briefs and into something more modest. But what the hell. Jamie had seen me round the pool in these togs and the shorts didn’t exactly reduce my gut or anything. I went outside, she was sitting on a lounge in a skimpy pink bikini, sunglasses perched on top of her head, applying sun cream to her legs. I sat and watched her as I sipped. Her skin was quite pale – despite having spent half the summer over here – and smooth. She was still quite adolescent in shape, a bit of puppy fat, smallish breasts, but shapely legs and her butt filled out her bikini nicely. Very nicely.

I finished my drink and got up for a second. ‘Wanna beer, Jamie?’

‘Uh, no thanks Mr D, I don’t really like beer.’ I shrugged. ‘But I’d love a vodka and orange!’ I shrugged again and headed inside. I fixed a more moderate scotch for myself, then the drink for Jamie, heavy on the vodka. She looked quite the try-hard wannabe sophisticate – lying back on the lounge, sunglasses, cigarette, cocktail. I chuckled inwardly and resumed my seat. It was good for a guy’s ego to have a pretty young thing almost naked about the place. I was conscious of her checking me out from behind her dark glasses and hoped I didn’t look too unattractive. I guess I’m carrying a bit more weight than I should, but my gut is smaller than most men my age, and it’s covered with a summer tan and a matt of brown hair that my wife always liked. And my arms and chest are still shapely enough from all the years of swimming. So all is all, I didn’t mind Jamie’s scrutiny, and anyway she’d been doing it all summer, even flirting with me when Suzie wasn’t around.

Jamie prattled on a bit about how boring her course had been, about music and so on. I didn’t need to contribute much more than a grunt every now and then. I swam a few laps and Jamie followed me into the pool, splashing about and making girly noises. I paused after ten laps and Jamie was sitting on the edge of the pool waiting for me to surface. Her open legs were inches from my nose and she giggled as she saw me staring at the tight fabric outlining her vulva. I had half a mind to tell the cock teaser to go home, but decided to splash her instead. She shrieked artificially and jumped in on top of me. We horsed around and she managed to press her tits against me several times and grope my butt and groin. I climbed out and dozed for a few minutes in the waning sun, while Jamie fussed with lotions and cigarettes. I took our glasses in for a top-up. When I returned, Jamie took her glass, had a gulp (not seeming to notice that it was almost a third vodka) then rolled onto her front and asked me to put tanning lotion on her back. I said the sun was so low that she didn’t need to worry and she tossed the hair out of her eyes and gave me a pouty look. I enjoy a bit of flirting and gave her a knowing grin.

‘So, like anyway,’ she said, ‘you haven’t said how you like my new tattoo.’ She had a dark blue celtic pattern in a swathe across the small of her back with a loopy arrow head in the middle pointing downward, its tip disappearing below her bikini line. It’s the kind of tattoo you see on women hanging around in malls and city corners. I had been kind of marvelling at it when she was splashing about in the pool. Jamie sure has a fierce instinct for downward mobility.

‘Well?’ she demanded, wriggling her butt in case I wasn’t looking hard enough.

‘I can’t see all of it, but I guess I like better where it’s pointing,’ I said, grinning again.

‘Mr D!’ she screeched in mock outrage, delighted that I was playing along.

We both took a slug from our drinks. I hunched forward and said, ‘So, are you going to show me all of it?’

‘Uh huh,’ she replied all bright eyed. She reached back and inched the hem of her bikini halfway down her butt. I was more interested in the yummy butt crack and swell of her pale cheeks, than the final swirl of the tattoo. She was watching me, mouth slightly parted, as she held her bikini down – longer than was necessary – then inched it even lower.

I got up and walked the three paces over to her lounge, then crouched down beside her. I ran my hand over her lower back, tracing the edges of the tattoo, then following it down to the parting of her buttocks. ‘It doesn’t do you justice,’ I murmured, massaging the firm mounds. Her eyes had widened and she was panting – nervousness? anticipation? I continued to massage her butt, nudged her hands away and pushed the bikini bottom further down, revealing the full glory of her 18 year old bum. I massaged it in a full round motion, managing to graze her perineum with my fingertips and trailing my thumbs through her humid cleft. I paused and nudged her thighs. She was quick to spread them wider and now I was able to touch her labia as I massaged.

‘You like that, Jamie?

‘Yes, Mr D.’

‘Do you want me to stop?’

‘No, Mr D.’

I kept up the massage, Jamie sighing as my fingers played with her bottom and labia. After a minute I tugged her bikini bottom al the way down and tossed it on the ground. Kneeling behind her, I pushed her legs wide and pulled her butt back and up so she was slightly on her knees. God it was a magnificent sight! Pink labia slightly damp from arousal, fringed with curly blond hair, a tantalising little path back between bulging flesh to a dainty little purply-brown crinkle. I leant forward and teased the labia open with the tip of my tongue. Jamie tensed and then gasped when I sought out her little clit hood, washed around it then swiped back deep between her labia. She tasted fresh and sweet and after a couple of moments her little bud had emerged from its sheath. I lapped on the clit making Jamie sigh and arch, then plunged my tongue back into her slick vagina. She was getting very wet and I delved deep for her juices between licking the now-straining clit. But it was her arse I wanted and it was time I paid it the attention it deserved. I made a long swipe up from her vagina to her anus, washed round the pucker and probed at its centre.

‘Jesus, Mr D!’ Jamie gasped. ‘What are you doing?’

By way of reply, I put my hands more firmly on each buttock and held them wide apart, pushing harder with my tongue. We both grunted when the muscle gave way. I reamed, Jamie moaned and we discovered that we were doing something we both very much liked. I got a finger on her clit and stroked it to the rhythm of my tongue. It was a technique I’d developed with my ex-wife guaranteed to bring her off and get her compliant for a solid buggering. It was a few years since I’d had an opportunity to use it and was glad to see it was working well on someone else. And Jamie tasted better than my ex – less earthy, less sour and less sharp. I dug deep, searching for that hot rectum flavour, and Jamie moaned in response. With my ex, this kind of action soon brought her off, but it was taking much longer with Jamie and my jaw was beginning to tire. I eased back on the clit action and slid the middle finger of my other hand into her oh so tight twat. She gasped when I found her g-spot and started up a steady moaning as I rubbed the velvety pad. She was getting close and I ate her arse with renewed vigour, maintaining the clit and g-spot diddling. Her bung hole was gaping, my tongue was jabbing deep in the fetid passage, saliva and arse butter were dripping down my chin, my fingers were slipping over her buttons. When she came it was with a wrenching heave that dislodged my face. I let her slump forward on to the lounge, my fingers coming free. Her mouth was open in a soundless scream, eyes shut and hands grasping at the lounge legs. Her pert butt was all splotched from my hands and as she writhed I could see her anus all glistening and pulsing. I couldn’t resist the temptation and bent forward. Jamie gasped and moaned afresh when I held her buttocks apart and sucked on the pulpy ring, still twitching from her orgasm. Her sphincter weakly gripped my tongue as she went through the dying throes, then her arse went slack. I gave it a good workout, pumping lots of saliva in for the action that was still to come.

I sat back on my haunches, my cock pushing out the front of my swimming briefs. Jamie looked back at me, her face flushed and lips moist. ‘Jesus, that was awesome,’ she said a little breathlessly. I smiled, leant forward and kissed her hard, letting her taste her arse on my lips and tongue. She didn’t seem the least averse as her tongue swirled against mine. For my part I got the unfamiliar taste of tobacco.

‘That good?’ I asked sitting back again.

‘A real first,’ she nodded, eyes all misty.

‘Never been rimmed before?’ I grinned.

‘Not that either,’ she said. ‘But I meant my first orgasm.’

‘You’re kidding!’ I said. ‘Never cum before?’ She shook her head. ‘How long have you been having sex?’

‘Uh, nearly four years, I guess. But it’s never been like this.’

Christ! I thought, wondering briefly about what kind of sex life she’d been leading, then mentally shrugged. There were more immediate concerns. ‘Well, you’re in for some wonderful times. But right now it’s time to return the favour,’ I said standing and moving so that my bulging trunks were before her eyes. She looked at the stretched fabric and the tip of her tongue wet her lips. ‘Suck me!’ I hissed, pulling up the left leg of my bathers and easing out my boner. Jamie sat up and engulfed the first half of my cock. She started a sloppy blow job, but wasn’t handling it too well. Clearly no-one had ever taught the kid to suck dick. After her teeth had grated against my glans a couple of times, and my pole had been almost bent in half against her jaw, I figured I was in danger of injury. So I pulled out and told her to suck my balls. With just a couple of directions she was doing a great job, tugging each one out in turn and sucking on it hard enough to make my cock twitch and knees buckle. It’s something that has always made my jizz rise, but my ex was always grudging about doing it, saying my balls were too hairy. But Jamie seemed eager enough so I let her do it for a nice long time.

‘Now I’m ready to fuck that beautiful arse,’ I said, tugging a reddened testicle from between her plump lips. She looked taken aback and I thought for a moment. ‘You have been butt fucked before, haven’t you?’

‘Uh uh,’ she shook her head. Christ! An anal virgin! My cock twitched and jizz boiled.

‘Well, it’s a day for firsts!’ I replied.

‘Won’t it hurt?’

‘Naahhh,’ I reassured her. ‘The secret for enjoyable anal sex is firstly lots of preparation – and honey there ain’t better preparation than being reamed out for 20 minutes! – and secondly, lubrication.’ I smiled and she looked less uncertain. I reached to her bag and took out the after sun lotion I could see there, and held it up. ‘And this will do just fine.’

‘But you’re so big,’ she said in a worried voice.

What the…? I’m not any bigger than average, just your regulation six and a half inches. Again I wondered what her sex life had been like. I just gave her a calm smile and directed her to go up on her hands and knees.

Once she’d assumed the position, I stood behind her and straddled the lounge, my feet on either side. It was low enough to the ground that I could fuck her like that and I applied lots of lotion, first to my cock and then to her butt. I was pleased to see that despite all the tonguing it had closed nicely and was back to its virginal tightness. I then shuffled forward and fitted my bulging cock head to the little glistening pucker. ‘Remember how good it felt when I was licking you?

‘Uh huh,’ she said a little uncertainly.

‘Well, this is going to feel even better.’ I pressed forward and after a moment her greasy sphincter gave way under the steady pressure. I could feel her ring clenching, but her hole was so well lubed that she couldn’t prevent my entry.

‘Yyaaaggh!’ she gasped as my purple helmet slid through her ring and lodged in her rectum. I paused to let her get used to it. Actually, her pucker was clenched so tight that I was in danger of cumming. Both of us were panting. ‘Take it out!’ she gasped. ‘You’re too big, Mr D!’

‘Hang on kid,’ I said soothingly. ‘It’ll get better in a minute.’ I reached forward and slid a finger in her mouth. She sucked it desperately and I fitted in another then gently fucked them back and forth. After a moment, she was distracted enough that I felt her butt unclench a fraction. I took the opportunity to drive forward and she immediately stiffened and gasped. But I wasn’t going to be denied this time and kept bearing forward until I was all the way in that hot glove like arse, my balls resting against the slimy perineum.

I was in danger of jetting again, right on the verge, and had to hold still. Jamie felt my cock pulsing. ‘Are you cumming?’ she asked in a hopeful whimper.

‘Uh uh, kid.’ I chuckled. ‘But when I do,’ I reassured her, feeling my staying power return, ‘you’re going to know for certain.’ I jagged a couple of fingers back in her mouth, got a fistful of her hair with the other hand and tugged her head back, causing her body to arch delightfully. She was taut as a bowstring. ‘And before then,’ I said, tightening my grip on her hair, ‘you’re going to know what anal sex is all about!’ With that I started some steady deep stroking, just the bottom third of my cock emerging from her pooper before ramming back in. She was going uuunnnhhh! uuunnnhhh! uuunnnhhh! and sucking hard on my fingers. Her arse was loosening up and she was handling the full depth OK. I decided it was time for something more vigorous and began to pound her with full strokes, screwing my hips hard each time I bottomed out. It was such a hot tight arse that I began to lose it a bit and fucked her pretty wildly, driving her down so that she was prone on the lounge, my full weight behind each thrust. After a couple of minutes I realised she was crying around my fingers and eased up a bit.

‘OK honey?’ I asked soothingly.

‘It hurts, Mr D!’ she whimpered.

‘Too dry?’ I asked making a couple of quick rabbit hunches. ‘Or too deep?’ I said driving as far forward as possible and pulling her hair so that she arched and took it that fraction deeper.

‘Please stop,’ she blubbered, and then sucked on my fingers.

I wanted to see her face as I fucked her arse; get off on her emotions. ‘I know what,’ I said. ‘The angle must be wrong.’ I let go her hair and stood back, my cock coming out of her butt and leaving it gaping. I looked for a few seconds until it closed. Then I told Jamie to roll onto her back. She did so and I hitched her ankles high on my shoulders and lifted those separated buttocks up high. She had her bottom lip caught between her teeth and was looking at me with wide apprehensive eyes. I told her to pass me the tube of cocoa butter and applied more of the thick grease to my reddened cock. I then fitted my cock to her date and pressed till it was on the point of giving way. I paused and looked at the kid’s face, wet where my fingers had wiped saliva, hair mussed. I gave her a reassuring smile. ‘Push back at me, honey. It will feel better.’ She did and her crinkle flowered and my cock slid in.

We both groaned and I paused, my cock half way in. ‘Feels good, doesn’t it?’ Her face was strained but she gave me an uncertain nod. I stayed like that and began to kiss and stroke her calves, then her feet. She squirmed when I got to her toes and giggled as I sucked slowly on each one. I don’t know if it turned her on or not, but I could feel her gut relax and gave her another inch of cock. She was smiling now. ‘Ready for some more?’

‘Uh huh,’ she smiled. I sank slowly forward onto her breasts, my cock sinking deep into her bowel. I kissed her hard and she responded hotly. I humped away as I forced her teeth wide, chewed on her tongue and bit her lips. Then I started fucking her harder, brutalising her arse as I brutalised her mouth. The little minx was up for it this time, her tongue duelling with mine, panting hotly with each thrust. I pulled back a bit and panted at her to tug her tits out of the bikini top. Then I was on them like a beggar at a banquet, feasting on the hard little nips and creating a pattern of bite marks on the soft mounds. She was heaving back at me now, trying to grind her clit against my pubic bone as I bore down. I went upright again and rubbed her cunny as I fucked her arse, making her hiss and toss her head. I did her that way for four or five minutes until she came, a fed flush spreading from her neck over her chest as she whimpered and groaned. Her clenching anus reminded me that I wasn’t far off and I gave her a nice stroking as she rode out her orgasm.

She looked up at me with smouldering eyes and pulled me down on her chest again. We kissed and this time it was her who bit and chewed. She was hot and I was close. ‘Do you like the taste of cum?’ I panted, sweat dripping off my forehead onto her splotched chest.

‘Uh, not really,’ she panted back, not realising what I was about to do.

‘Well. I understand it’s an acquired taste,’ I grunted suddenly pulling out of her butt and crouching by her face. I grabbed her hair and pushed my greasy shit streaked tool against those bruised lips. Her eyes flew wide but I jagged forward and into her mouth. She was totally passive, her eyes showing her distaste. I slapped her cheek not so gently and hissed at her to suck. Startled she complied and I groaned as I felt my balls begin to boil. ‘Work my balls!’ I demanded and I felt a hot little hand cup my sac. ‘Yeah, baby!’ I moaned as the double action of mouth and hand worked their magic. She sensed how close I was and started to apply herself with a will. Looking down at that girlie face concentrating on my cock, a fleck of shit caught in the moist corner of her mouth as she bobbed back and forth on my shaft, was enough to bring me off. With a straining jag forward of the hips and a long grunt, my balls emptied. I held her head in place while my cock pulsed and jetted, her gagging sounds making it all the more intense. Finally I was finished. Panting I looked down at Jamie, my hand still wrapped in her hair holding her to my softening cock, a trickle of thick sperm oozing from one corner of her mouth.

‘Swallow,’ I ordered and waited till she’d done so before releasing her and tugging my cock from between those plump lips. Then I knelt beside her and kissed that hot bruised mouth, tasting the remnants of my seed. It took her a few seconds to respond, but when she did, it was with some enthusiasm.

‘So, kid,’ I said, sitting back on my haunches and stroking her thighs. ‘Enjoy that?’

‘Uh, huh,’ she said, eyes sparkling. ‘Maybe not all, but … yeah, I guess all!’

‘Great!’ I smiled back. ‘I’m just going inside to get another drink. You want one?’ When I came back out with the glasses and a cloth to wipe clean the lounge, Jamie was lying back smoking, one hand gently massaging her blotched breasts. I handed her the straight orange juice and watched as she gulped it down. Then I packed her off back home. She whined and carried on wanted to stay knowing that I’d be alone all night, but I didn’t want her to get the wrong idea. It was only sex. She pouted, whined and begged so I told her she could come back the next Thursday when I’d be alone again. Afterall, I reasoned, someone ought to teach the kid how to suck cock. That is, if I could keep away from her arse long enough …..

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Anal Sex At The Football Game

I have wanted to tell this story for a long time now. And with football season about to start again, I just have to get it out. It was last year in November during an Oakland Raiders game. I was sitting drinking a beer when this drop dead gorgeous blonde walked down my aisle. I tried to make eye contact and she gave me the ol’ “not if you were the last man on Earth” look down her nose.

Well that made me want her even more and so I stared at her perfectly round ass that swayed in a short dress with each step. As she turned I saw her huge boobs were barely contained by the low dress and I wondered what in the world was she doing here? I got all my buddies to check her out and agree she would be one hell of a hot fuck.

The next thing you know, she is standing at the front rail leaning forward, giving us all a good look at the shape of her ass and the thong splitting her nice round cheeks. She was leaning forward to show off those big boobs! And half the stadium was watching them instead of the game, including my friends and me.

I got a brainstorm (in the head between my legs) and said “let’s go down there” to my buddies. She was much too caught up in the attention to notice us surrounding her. In fact she hardly noticed me grinding my hard cock up against her ass at first. When she did notice she also noticed the crowd of guys pinning her in and also that everyone in the stadium would see if she made a scene. So, she whispered “bastard” at me while smiling down at the crowd and leaning forward to make her boobs jut out even more.

Knowing that I had the advantage, I edged her dress up until my hands could roam her soft white ass cheeks. She pushed back with her ass (like that was going to scare me off) and I replied by pulling my stiff cock out of my pants and pressing it between her ass cheeks. Her eyes went wide at that but just then a TV camera focused its attention on her and she again became all smiles for the crowd. This was way too much to pass up and I pulled her thong aside so my cock to probe at the opening to her pussy.

I was so surprised to be greeted by a sticky wet sensation. She was wet! All this crowd attention was turning her on! One quick thrust and I had half my cock in her pussy. “Oh you fucking bastard” was all she had to say as I started to fuck my cock in and out of her hot pussy. I could just imagine her lips were strawberry pink and dripping woman cum as I sank the last of my 8 inches into her. She groaned and leaned forward some more, her ass lifting as she did so, giving me even more angle to fuck her in front of 80,000 people. The crowd was cheering now as though they knew she was about to cream all over my cock when I realized one of her beautiful boobs was about to pop loose. I rotated back and forth in her, both trying to make her boobs break free and trying to get her off so she wouldn’t be able to stop them.

But she was even hotter than I thought she was and with a really nasty groan she came, juices dripping down both our thighs. A “squirter” I thought as she tried to suck the cum right out of my balls with her pulsing pussy. I looked down to admire it and was greeted by her brown ass hole looking back at me. It didn’t look all stretched out but I had a feeling that she had been ass fucked more than once and would enjoy getting it again.

I pulled my cock out of her still throbbing pussy, lined it up with that brown winking eye, and thrust right into her unto my balls slapped against her sticky, juice covered pussy lips. Now she let out a guttural groan and at the same time both boobs burst out of her dress. The crowd’s cheers drowned out the sounds of her groans as I plowed her ass with wild abandon. It didn’t take long and I could feel my cock head swelling up and ready to explode! Her ass was so tight; maybe she hadn’t ever had a cock in there after all. Then just as I shoved my cock all the way in and ground it in even deeper, I let loose with the biggest load of cum I’ve ever had. It shot all the way up her bowels filling her ass with my hot sticky semen. And she responded to that with an orgasm that made all other orgasms pale in comparison. She shuddered and moaned for a good 2 minutes, sucking every last drop of cum out of my cock with that beautiful ass.

As she finished the last spasms of her orgasm I pulled my cock out with a loud plop. Definitely an anal virgin no more! We all slowly walked away while she stuffed her gorgeous boobs back into her dress and backed away from the rail and all her admirers. Fortunately all the TV camera could see was a sexy blonde woman showing off her boobs and pretending to have an orgasm for the crowd. While some stranger stood close behind her with a look of obvious enjoyment on his face.

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Head Cheerleaders Anal Cherry

The year was 1994. I was 18 years old and about to graduate high school. The prom was only a week away and I did not have a date. I was an average looking guy. I was 5’10, 190 lbs, short dark hair, and dark eyes with a decent build. I guess my best quality was tucked away in my pants. My dick was nearly ten inches long and very thick. Having had a girlfriend in private school for three years, whom I had just broken up with, word had not really spread throughout school about my goods.

Through out my senior year I was in love with the Jeanine. She was the captain of the cheerleaders, the Student Government President and had been elected homecoming queen easily back in the fall. However, she had been dating this guy named Dan and I figured since they had been together for two years, they were never breaking up.

Much to my surprise the week of the prom, Jeanine & Dan broke up and Jeanine was now dateless to the prom. I seized my opportunity and asked her to go. Since we were friends and she knew, I too was coming out of a relationship, she figured we would have fun.

The night of the dance, Jeanine looked gorgeous. Decked out in a black strapless dress, that ended two inches above the knee, her 34 C tits were well accented and of course her blonde hair and blue eyes started giving me dirty thoughts as soon as she opened her front door. To make matters worse, Jeanine was wearing this sexy red lipstick and all I could think about was what it would be like to have her luscious lips wrapped around my dick.

I got a limo for Jeanine and me since she did not want to go with her friends because Dan would be there with his date. I took her to dinner and then off we went to the prom. In the limo we shared a bottle of wine and we were both feeling very good as we entered the prom. I was loving life considering I had the hottest girl in school on my arm.

Jeanine was also a member of the school dance team so needless to say she was a fun date. It was during the song Rump Shaker by Wrecks N Effects that I knew our night might get interesting. Freak dancing was huge at the time and during this song I was behind Jeanine who of course at the start of the song was grinding her ass on my cock. I could not stand it and got full erect almost immediately. Jeanine reached one hand behind my neck and pulled me in and whispered into my ear, “Easy tiger.” As that song ended a slow dance came on and of course Dan came over and asked if he could cut in. Jeanine said no, and of course Dan made a scene. I suggested he go back to his date but instead he pushed me. So I clenched my fist and clocked him in the nose. Jeanine smiled and thanked me, a few others patted me on the back, but the principal suggest I leave.

Jeanine and I got in our limo and she immediately grabbed face and stuck her sensational lips on my mouth and kissed me deep. Her tongue darted into my mouth and did amazing swirls. It was with out a doubt the best kiss of my life. She tasted so sweet and I wrapped my arms around her, held her tight and enjoyed her tongue in my mouth. As we were kissing, I could not help myself and had to grab her ass. It was so firm and of course the perfect size. I mean after all, she was a cheerleader and dancer. She stood 5’4″ weighed 115 lbs.

After a few minutes of kissing, the phone rang and the limo driver asked us where we wanted to go. It was 11 o’clock and we had the limo until 2 AM. Jeanine told him to just drive us anywhere he wanted and keep the car moving. She told him we just wanted to ride around until 2 AM. Since we were in Baltimore, I think we drove to DC, followed by Annapolis, but I can’t remember.

Jeanine hung the phone up and turned back to me and noticed the bulge in my pants and smiled. She said, “I thought I felt a monster pocking at my ass while we danced.” I replied that the monster loved the feeling of her ass.” It was a lame line, but I did not care.

She kneeled in front of me (gotta love limos) and said that she was not looking for a relationship and I was probably a rebound. She said she was going to college out of state and was not looking to start a relationship. She also said that she was fucking a guy with a little dick for two years and wanted nothing more on prom night then to fuck a man who could really make her cum.

With that in mind she undid my tux pants and slid them down to my ankles. Since I don’t wear underwear my cock was fully erect and the near ten inches just popped into her face. She started to lick the head of my dick. The tip of her tongue teased the opening of the head of my dick and drove me wild. She used her right hand to hold my cock and her left hand was massaging my balls. After a couple of minutes of licking the head of my dick, Jeanine pulled away and popped her boobs out of her dress.

She then leaned forward, opened her mouth and wrapped her red lipstick clad lips around my cock and started to suck. Her combination of lip pressure and tongue licking was amazing as her head bobbed up and down on my cock. The entire time as her mouth moved up and down my dick, Jeanine kept massaging my balls. She even stopped sucking my dick after about six minutes and took the time to put each ball in her mouth and suck them one at a time while stroking my shaft. At this point I was squeezing her tits and her nipples were rock hard.

After sucking my balls for a while Jeanine brought her sexy mouth back to my shaft and continued with the best blow job of my life. Her bobbing head was now doing its best to deep throat me. She got about 75% of my cock in her mouth, but my thickness and length was too much for her. So I decided to help. I placed my hands on her blonde hair and head and skull fucked her. I pushed my cock all the way to the back of her throat and at this point her nose buried in my pubes, but my whole cock was in her mouth. I held her in place. She gagged for a second or two but then she adjusted and I helped her resume her blow job, though now she was deep throating me.

Between her tongue, her lips, the fact she was deep throating me and of course her hand that was constantly massaging my balls, I could not take it any more and exploded a massive cum shot into her mouth. AS soon as a drop of cum hit her tongue I could feel her mouth become more like a vacuum as she literally tried to suck all of the cum out of me. I am lucky in that I shoot massive loads of cum and it turned me on so much seeing her try and swallow every drop, but still see a little bit creep out the corner of her mouth.

Jeanine removed her lips from my dick and I was thrilled to see that there was a small amount of red lipstick around my shaft. She used her finger to capture the small amount of cum around her lips and guided it into her mouth. She smiled and said, “Now you know why I was elected head cheerleader.”

There was no way I was not returning the favor as I was hornier now then before. I pulled Jeanine onto the seat and angled her off the seat so her pussy would be right in my face. I lifted her dress up so it was around her waist and much to my surprise she too was going commando. Even better was her pussy was shaved clean. So smooth and perfect, a true bald eagle.

I spread Jeanine’s legs and began licking her throbbing clit. She was so wet and tasted so sweet. Her clit was very thick… Her actually pussy hole was even better. It was soaking wet and easy to stick my tongue into. I stuck my tongue as deep into her pussy as I could and still worked her clit with my top lip and thumb. As I was eating her pussy, I could not help but notice how sexy her asshole was. I knew she had a great ass, but there was something about her asshole that was turning me on.

I had a lot of experience with anal sex before, but never, had I licked a girl’s ass. It was then I decided that I was going to taste Jeanine’s ass, only first I needed to make her cum. I wrapped my lips around her clit and sucked it very hard as my tongue worked the rest of her pussy. It did not take long, and Jeanine exploded into an orgasm. Jeanine came so hard she was pushing her entire pelvis into my face and I just sucked her clit harder. She was begging me to stop but I kept at her. Finally she pushed me away. Using my finger I gathered some of her juices and guided them down to her asshole. Before she had a chance to realize what I was doing I leaned in and stuck my tongue straight into her sexy tight bung hole. I was expecting it to taste lousy but it actually tasted really sweet.

I gave her asshole a good licking for a few minutes and in the mean time started to finger Jeanine’s pussy. I could tell by the way Jeanine’s body was tensing up that she was about to cum again. So I decided to go with the world famous, “two in the pink, one in the stink method. I licked her clit fast as I fingered her pussy with my pointer and middle finger and fingered her ass with my pinky. Jeanine exploded again and came really hard, this time squirting some visible juice.

I was rock hard again at this point and with out a condom, shoved my cock right into Jeanine’s pussy. It was so wet and so tight and so hot. My huge cock stretched her wide and in seconds her legs were over my shoulders so I was able to get all 9.5 inches deep into her. I swear I think I hit her cervix because she exploded into another orgasm. Her cumming only made me fuck her harder and I am pretty sure she came again about 30 seconds later. My cock was easily flying into Jeanine’s pussy at this point and my balls were smacking her asshole.

Jeanine and I moved onto the limo floor and she got on all fours, using the seat for leverage, and I entered her pussy from behind doggy style. I started out holding her hips and pounding her pussy really hard. I was fascinated seeing her pussy just suck my entire dick in and spit it out. I leaned forward so I could get deeper into Jeanine but also so I could kiss her neck. I wrapped my lips around her neck as my hips pushed my cock in and out of her pussy and left a pretty big hickey on her neck.

She reached back and scratched my back drawing a little blood. I moved back to holding onto her hips and licked my finger so I could stick it into her ass. That was all it took and Jeanine exploded into another orgasm.

I decided to go for it and try to fuck Jeanine in the ass. I pulled out of her pussy. My dick was so wet with her pussy juice. I pushed the head of my cock right up to her asshole and started to push. She freaked and asked what I was doing. I told her to relax, trust me and to rub her clit hard and fast. She obeyed and I pushed my cock hard into her ass. Her tight sphincter resisted but eventually gave way and started to expand. Jeanine yelled in pain, I asked her if she wanted me to stop, but she told me if I did she’d never fuck me again.

I went slow and eventually the captain of the cheerleader’s asshole was full wrapped around my dick. She took all of me in her butt and after a few minutes, she told me to pump her. It turned me on to no end. I felt like I was going to cum, but did my best not to. Jeanine, told me to lie down because she wanted to try riding my cock with her asshole. I did as she commanded and with her dress still around her waist she lowered herself onto my cock and I slid back deep into her gaping asshole. Jeanine seemed to really like it. She bounced up and down on my dick and was going really fast. It was so sexy to see her asshole gaping wide swallowing my cock. I was rubbing her clit as fast as she was riding me and of course her tits bouncing made the view perfect.

I was about to cum and I told her I wanted to cum inside of her. She switched my dick from her ass and clamped down on me with her pussy. I reminded her I was not wearing a condom but she did not care. She bounced on my dick three times faster now that I was in her pussy and within seconds, I exploded into my second orgasm of the night filling her up with cum, I could feel my cum shooting deep inside of her.

She fell forward and we kissed. My cock was still in her pussy and I was still semi hard and still having small cum shots go into her pussy. She finally got off of me and collapsed next to me. She smiled and told me that I was her first ass fuck.

I nodded off to sleep as the limo driver drove knowing that I fucked the head cheerleaders virgin ass. About 45 minutes after we were done fucking it was 2 AM. I slept over at Jeanine’s and the next morning she woke me up with a great blow job. We pretty much fucked for the entire summer and then stayed in touch through college. Whenever we were home on breaks we’d always meet up and fuck for hours.

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