First Time Anal by the Poolbyquietcantor©
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.