Written by Mark

21 Jul 2015

I left school at eighteen, unlike most of my friends still a virgin. I took a gap year, travelling for some of the time, with high hopes of getting my first shag. No such luck. Off to Uni still hopeful of losing my virginity. I almost did, a girl who had the reputation of being a slut who'd let anyone fuck her. Back to her room, naked in bed, I got to touch a pussy for the first time. She stroked my cock, I was almost instantly hard and realised I wouldn't be able to hold back for long. Eager for my first fuck, I rolled between her open legs, then to my intense embarrassment ejaculated on her shaven pussy, shooting spunk on her tits when I leapt off. I'd come before my cock had even touched her cunt, let alone entered her. I mumbled an apology, dressed and left. To make matters worse she took great delight in telling everyone what had happened. I spent months having the piss taken by the guys and listening to the sniggers of the girls.

I'm not a bad looking bloke, about 6 feet tall, slim and fit. Judging from the initial reaction of the girl, in the minutes before I prematurely shot my load over her, women would be quite impressed with my cock. About 9 inches erect, for all the use it was to me. Confidence well and truly undermined, I watched and read loads of porn and became an inveterate wanker. I discovered this and similar websites and a few times last summer, visited some of the listed dogging sites. Several times I was lucky enough to watch a number of women masturbating, sucking cocks or being fucked.

One woman seemed to be inviting all the men watching to fuck her. She'd sucked several cocks and been fucked by at least a dozen guys before she noticed me wanking in the shadows. She called to me asking if I wanted to fuck her. I was rooted to the spot and shook my head. “I'll suck your cock if you want. I swallow” she offered. She turned her attention to someone else as I slunk off. I watched and wanked from behind a thick shrub until I came, while some lucky bastard fucked her. A tale of sexual failure if ever there was one.

However, a few weeks ago I finished at Uni and returned home to stay with my Mum whilst searching for employment. She soon got fed up with me staying bed, computer gaming and generally doing nothing. When one of her friends returned from holiday and needed help in her garden my services were immediately volunteered. Sally is about 45 years old and separated from her husband after he found out a guy she worked with was fucking her. Years ago she used to babysit me. An attractive woman, tanned from her holiday, a nice figure and amazing tits, (40dd I discovered when I checked the label on one of her bras drying on the line). As a teenager I'd had many a wank imagining her.

The first two days were cool, overcast with showers and rain and we didn't get much done, but I had opportunities to admire her shapely bum, clad in tight jeans, each time she bent over. The third day was hot and sunny, I turned up about 9am, in shorts and T-shirt. Sally was already in the garden, once again in jeans, the coat of the previous days gone, wearing a T- shirt. I got down to work, trying not to, to obviously stare at her tanned tits, encased in a lace bra, whenever she leant forward. I thought I was being careful until she caught me and suddenly said, “Enjoying the view. Do you think I've got nice tits?” I looked away, felt myself blushing, mumbling an apology. She laughed, saying she didn't mind me looking.

She carried on working, deliberately leaning forward tempting me to look, before telling me she was going to change out of her jeans into something cooler and fetch us drinks. Whilst she was gone I had the chance to try and calm down, though my cock stubbornly refused to go completely soft each time I thought of her tits. She returned after about 10 minutes, walking down the path carrying a drink in each hand, wearing a tiny pair of bikini bottoms and a crop top that barely covered her tits. Still kneeling, looking up as she stood in front of me, I admired her mature womanly curves. Nice shapely tanned legs, wide hips, rounded belly but not fat. I raised my eyes higher, I could see the underside of her braless tits, tanned as darkly as the rest of her, except for a pale line underneath each heavy boob.

More than likely my mouth was hanging open. She knew exactly what I could see and the effect it was having. She squatted, opening her legs as she handed me my drink. I glanced between her legs, noticed the material pulled into her pussy, a noticeable cameltoe and damp patch darkening the white bikini. She took a sip of her drink, licked her lips suggestively, put the glass down on the paving. “You don't mind if I take this off. Top up my tan, do you?” she asked. Without waiting for an answer she pulled the crop top over her head and dropped it next to the glass, revealing her magnificent, large, round firm tits, the dark nipples, erect and poking out. I could hardly drag my eyes off them, except to glance in panic towards the house next door. I was relieved that none of the windows overlooked that part of the garden. “Don't worry. No one can see. I often sunbathe out here nude ” she told me, a smile on her lips, amused at how nervous I was.

I took a gulp of my drink, put it down. She stood, “Is your cock still hard?” she asked, eyes focused on my crotch. I'd been doing my best to hide my erection. Startled, I nodded, looked away, then back again when I realised she was untying one side of her bikini pants. Half the front dropped partly uncovering her pussy. She held it so it wouldn't fall. Moved closer, “Untie the other side for me” she told me huskily. With shaking hands I untied the string, she let go and the bikini fluttered to the ground. Her pussy was smooth, completely hairless, tanned the same as the rest of her naked body. She moved her legs apart, her cunt winked open, glistening with her juices. “You can lick me if you want” she invited, moving closer, putting her hand on my head, pressing my face between her legs.

I didn't have much choice, she was holding my hair, rubbing her cunt against my mouth. I stuck my tongue out and began to lap her pussy, tasting her sex. She loosened her grip a bit, allowing me to breathe more easily. For several minutes I eagerly, if inexpertly, probed her mature cunt with my tongue, her juices flowing into my mouth. She moved her legs further apart, thrusting her cunt against my face, “Suck my clit” she demanded, pulling my hair. I found her clit, took it between my lips, sucking it hard. I felt her shudder, her legs shake. She began to grind her cunt against my face, sighing, with pleasure, repeating over and over, “Oh my god, Oh my god, Oh my god” getting faster and louder. “OH MY FUCKING GOD. I'M CUMMING. DON'T STOP. I'M CUMMING. I'M CUMMING. OH MY GOD. YES, YES. YES” She clamped her legs together, gripped my head tight. Her body trembling she came with a loud satisfied moan, squirting what tasted like a mixture of sex juices and piss in my mouth.

She loosened her grip on my head, still breathing heavily, she pulled me to my feet, dragging my T-shirt over my head. She grinned at me as she recovered, kissed my neck, traced a wet line down my chest with her tongue, licked my nipples. She stopped, looked up at me “You've got a good tongue, let's see what you can do with your cock” she gripped my shorts and pulled them and my underwear down. I was rock hard, but all I could think was that I was going to cum, any moment, just like the last time. “Oh wow. You must be popular with the girls” she sighed when she saw my cock. I think I snorted “I wish” thinking don't cum, please don't cum. I felt her warm breath on my cock, her tongue flicked out, licked my knob and I shot my load on her face.

The shame, embarrassment. I told her I was sorry. She stood up, my spunk running down her face, dripping on to her tits. She still had hold of my softening cock. I expected her to say something humiliating, instead she told me not to worry, she'd soon get me hard again and I could fuck her. I said I thought it would be better if I left. She disagreed, leading me by the cock into the house and up to her bedroom. I sat on the bed while she cleaned herself up in the en suite. I would have probably legged it if I'd had my clothes. She returned, climbed on the bed and asked if it had happened before. I told her once. “And other times?” I admitted there hadn't been any. “Are you saying you've never fucked a woman. You're a virgin?” I nodded and before I knew it my whole sad story was pouring out.

She listened sympathetically, commenting what a bitch the girl had been, as I told her everything, watching porn, wanking, even going to the dogging sites to watch. Her ears pricked up at that. She put my hand on my cock and told me to wank while I described in detail what I'd seen. She sat at the opposite end of the bed, legs open, told me to relax and she'd try to help me. She began rubbing her clit before slipping her fingers into her cunt, masturbating while she listened and watched me wanking. Having her masturbate in front of me had the desired effect and I began to get hard again. After a few minutes she reached into the bedside cupboard and took out a large vibrator, handed it to me and asked me to use it on her.

She was already very wet, her cunt gaping. I switched the vibrator on, it must have been about 2 inches in diameter but slid smoothly into her hole. I began to move it in and out, fascinated and excited by my first close up view of a woman's sex, her pussy lips opening and closing, her clitoris appearing as I fucked her with the artificial prick. Engrossed I hardly noticed her moving so she could reach my cock. She cupped my balls, giving them a gentle squeeze, then lightly ran her fingers up my shaft, little more than a tickle.

She continued like that, my cock throbbingly hard, just teasing me, slowly, almost imperceptibly, wrapping her fingers around my pole, delicately wanking me. She reached between her legs, took my hand and pulled the vibrator from her pussy, rolled onto her side and began to lick my cock. It was almost torture, the tip of her wet tongue gliding along my shaft from my bollocks to the tip. She did it three times, the third time she stopped and told me she was going to take my cock in her mouth. “You should last longer now. Warn me if you're going to cum” she told me. “OK” I gasped, as she opened her mouth and took my knob between her lips and began to softly suck me.

It felt fantastic, but after about half a minute of subtle sucking, I warned her I was close. She immediately stopped sucking me, took my shaft between finger and thumb, squeezing firmly just below the glans until the urge to ejaculate subsided. She moved kneeling astride my legs, resumed sucking me, repeating the squeeze each time I warned her I was going to cum. She was gentle and patient, eventually sitting up, sliding up my legs, holding my cock softly against her shaven mound and stomach “Do you want to fuck me now. Same as before. Say if you're going to cum” I wanted to fuck her more than anything and nervously said I did.

She held my cock steady, raised herself, moved above me. She lowered herself, guiding my cock towards her cunt. I felt the tip touch her hole and her rubbing it along her gash and clit. I lay there my body rigid, trying to imagine anything but sex. “Relax, you've already cum once. You'll be OK” she encouraged. I tried to relax, looking into her smiling eyes as she lowered her cunt onto my cock and I began to enter her. I wanted to look, see my cock in her cunt, but didn't dare. Very, very slowly she sank down, inch after inch of my solid cock slid into her until I felt her smooth pussy touch my pubes and I realised I'd fully penetrated her.

The relief was immense, my cock was inside her and I hadn't cum. She kept still for about a minute or two,using her cunt muscles to gently squeeze my cock. She began rocking, back and fore, rubbing her cunt against me, her heavy tits moving. She leant forward, inviting me to suck her nipples. I took one in my mouth, big and rubbery, suckling one nipple then the other until she sat up. She began to ride me, her tits slowly swaying as she rose up and down. She went up on her knees until my cock was just inside her. I risked a look as she sank back down, watching as my cock disappeared inside her fuck hole. Up she went again, I realised I was getting close and told her. She reached between her legs, pinching my cock until I felt the urge subside and she continued to ride me.

She kept her hand between her legs. I could feel her fingertips touching my prick as it slid in and out of her cunt and she stroked her clit. She rode me a little faster, stopping and squeezing twice more. After the third time she began to rub her clit faster, riding my cock more vigorously, her heavy tits swinging hypnotically. She began to moan, I warned her I was going to cum. “Do it. Cum in my cunt” she gasped, frantically massaging her clit.. I ejaculated spurting my spunk deep inside her. Her cunt seemed to pulse, her body going stiff, a pink flush spreading. She grabbed her tits, pinching and pulling her hard nipples, as she climaxed and I dumped another smaller load of spunk in her cunt.

She collapsed on top of me, laid there for a minute or two holding me until my softening cock slipped from her pussy. She kissed me on the mouth, then rolled off, covering her cunt while she hurried to the en suite to wipe herself. I was still blissfully laid on the bed when she returned. “Come on you lazy sod there's gardening to be done. You can fuck me again later” she grinned, grabbing my cock, pulling me off the bed.

She insisted that we continue the gardening nude. Her motive obvious. Seeing her naked, beautiful tits jiggling, cunt wet, gaping and inviting was arousing. She kept stopping work to play with my cock until I was erect again and I fucked her doggy in the centre of the lawn. I still had to stop several time as she pinched my cock, but I lasted even longer before I ejaculated.

Since then we've fucked every day, sometimes 3, 4 or 5 times. With her help and patient guidance I'm progressing and nowhere near as trigger happy. I, as you may recall, have been to dogging sites. Sally was fascinated by what I told her I'd seen and wanted to visit one, not just to watch but participate. We went last weekend. That is a story for some other time if you're interested.