FIRST THREE-WAY by Bill
I'll tell you about my first time, the day I lost my virginity. I can't remember if you know that I was born and lived in Scotland, then, when I was 21, I moved to Glasgow, because of my job with 3M (UK). Although I'd had some 'playing around' at school and had jerked off with another kid in the moors near my home, I still believed I was straight and got engaged when I was 21. Two years later I met this guy at a swimming pool and fell head over heels. He was very good looking, about 6'0" tall, lots of chest hair and I noticed the large bulge in his swim trunks. Half an hour later we were both in the shower room and while awaiting a vacant stall, he stood beside me. I was surprised to feel his left toe curl over my right toe. I stared at him and he just smiled, glancing down I realised he had an erection and this gorgeous, happy smile. I didn't move and he introduced himself as Jamie, 25 years old, a theatre stage manager and living in Glasgow.
I offered him a lift back to the city and gave him my phone number. Then began this incredible courtship and I was chased relentlessly with flowers, theatre tickets, dinners, etc. He invited me to stay one night after the show, we both pretended I was a little drunk and easily let him strip me. It was winter and cold and he hauled this quilt over us and minutes later I was in his arms, kissing, stroking his chest hair, our cocks hard and pressing against each other. He knew I was naive and slowly and lovingly introduced me to the delights of fondling and deep kissing. I was a little shocked when he rubbed his forefinger around the rim of my hole then sucked the finger into his mouth. Then he got between my legs and I was in heaven as his hot mouth, gently at first, then with determination sucked my cock till I screamed and filled his wet mouth with my hot load. Immediately he kissed me and pressed some of my cum into my mouth. Surprised at myself for enjoying the taste I swallowed and next he squatted over my face and rubbed his hard uncut cock against my face. Like it was an everyday occurrence I opened my mouth and his 9" and thick cock slid into my head. I was a dreadful cock sucker that first time and eventually Jamie held my mouth open with his fingers and stroked into me, blasting his cum onto my tongue and into my throat. I gagged but swallowed and we kissed and cuddled all night.
A repeat performance in the morning, resolved me to break off my engagement, a dramatic and painful operation, and I moved into Jamie's apartment. We were head over heels in love with each other and the only problem was that I wouldn't let him fuck me as he was big - 9" and very thick, 6.5" around. Every time he tried to penetrate, I screamed the place down - It became a real problem between us as he was desperate to mount me - we tried everything, poppers, trying it in afield where no one could her my screams, his finger, lots of lube but no use. I encouraged him to pick up guys to relieve his frustration and would lie there beside them on the bed, watching the naked guy, in ecstacy, being fucked by my lover's thick hard cock, while I held the stranger's hand. I always got to suck Jamie's cum out of the guys well stretched and dripping hole.
Finally Jamie came up with an idea that he'd give up first bite at my cherry in exchange for the key of the orchard!!!!! I agreed reluctantly as I loved him so much and, on a wet Sunday afternoon, one of the male dancers in the show arrived at the apartment. His name was Ray D, a good looking guy of twenty two, 6'0" tall and slim and a happy grin. After a couple of drinks we started playing 'spin the bottle' staking our clothes. Quite soon we were all down to our white briefs, hard and fondling each other. Jamie said "Ray, I want you to fuck Bill, he's still a virgin but I'm too big for him, so be careful, he needs it very badly and I need to screw him.
Ray already was aware of the reason this was all happening and knew why he was there but his eyes still lit up as, getting into a virgin ass was a prize especially when the lover was encouraging it and would be watching and touching.
We stripped off our briefs and started sucking each other, I had Jamie's big dick in my mouth and he was sucking Ray's thin six incher while Ray swallowed my 6" Jamie had a huge jar of Vaseline and I felt Ray rubbing it around my tight hole but not attempting to open me. The two horny men, each with a raging hard on, got me onto the towel-strewn double bed. They put me on my face and spread my arms and legs wide. Jamie got on one side of the bed and Ray on the other and they began massaging my arms and neck with baby oil My dick was surging underneath me as they moved onto my back, rubbing the oil well into my skin and all the time telling me to relax. Reaching my butt they concentrated on the ass cheeks but avoided the 'between my legs' area of my ass-crack although they pulled open my cheeks to get a better view of my virgin pucker.
Then they reached my feet, which was funny as I have immensely ticklish feet, and I was screaming loudly but with laughter, not pain: Next my calves bending my legs back and out and rubbing my well muscled legs and finally the target. By this time I was in a state of euphoria and when they sprinkled the oil all over my ass I almost came, it was so intense. Jamie and Ray took turns at massaging the oil into my ass crack and I felt a well lubricated finger slide in to the first knuckle. It was Ray's and he just let me relax on it. He called to Jamie to put a couple of cushions beneath my crotch with the result, that I was very vulnerable, my ass up and spread. They kept telling me how good I looked in this position. "Like a lamb waiting to be slaughtered" I giggled. I felt Ray climb onto the bed and, with his knees, force my legs even further apart He inserted a second well greased finger all the way in and I gasped with surprise. "I'll shit" I screamed "No you won't" said Ray "It's just your sphincter opening up" Jamie, meantime, was caressing me and saying "Relax Bill, you'll like it, I promise you, just relax, let it happen and I suspect that once you've been done you'll want it again and again" (In that statement he was ABSOLUTELY correct (grins))
Ray finger fucked me for, it seems like hours and I began bucking my ass against them, sucking them into my well greased hole, gripping them and realising how good this felt. I lay there moaning "I like this, I like this" feeling him draw out his slippery fingers. Next I felt his strong but narrow dick head push slowly into the opening of my tight virgin ass. I clutched at Jamie's hand as Ray suddenly stopped all movement when halfway in and told me to clench and unclench my ass muscles. He flexed his cock a few times and it felt a lot better. He pushed it all the way in - I gasped - but it was in pleasure not pain and he started gently fucking me, drawing out almost to the head then pushing in again. I screamed "More Ray, faster" and he opened up on me pounding my hole while I grabbed Jamie's hard dick and balls. "Getting near, can I shoot it into Bill" he asked Jamie "Yeah Ray, shoot it into him, it'll keep him lubricated, let me hold your balls against Bill's while you pump it into him". The pounding continued till Ray screamed "I'm cumming Bill" and pressed deep into me. Underneath I felt the joy/pain of a bursting ejaculation as I spilled my own cum onto the bed.
With Ray collapsed on me, his dick softening, I moaned "Jamie, NOW, I need more" so Ray pulled out his slimy greasy blood flecked cock. Jamie slid a finger into me, sucked it, then mounted me. He got between my spread legs and eased his monster just in till the helmet was locked. He kept telling me "Relax" as Ray slid his cock, still wet with his and my juices into my mouth and commanded "Suck". I slurped it deep in my mouth then felt the massive stretching of my ass walls as Jamie entered me. My tunnel felt like it was being split - as indeed it was, I let out some low moans of pleasure and soon his shaft was completely wedged in me. A couple of minutes later he started a gentle rocking each time his dick moving forwards and backwards in me. I could stand it no longer "I love you Jamie, ride me hard, fuck me deep, It's so-o-o-o-o good" I started screaming "More man, More, fuck me like a stallion, ram it in and out" He couldn't last much longer and I felt his cock swelling and knew I was being filled with his thick juice - We screamed loudly together "I love you" and he collapsed on my back, his gorgeous body drenched with sweat and his column of love still stiff and deep inside me. We kissed and tongued each other's mouths and Ray appeared from the kitchen, grinning from ear to ear, with a bottle of iced champagne.
Still on the champagne we all got hard again and I begged for it again (a born slut (laughs))
This time Ray took me on my back with Jamie at my head, rubbing his cock over my face, gripping my ankles and urging Ray on as he watched the gleaming shaft sliding into me. Ray took longer this time, twisting his cock around in me, sometimes, gripping it and teasing my ass lips with the head. Jamie began stroking his thick hard weapon, I moved a hand onto my erection, and we both shot our loads as Ray, eyes glazed, head thrown back, pumped his cum into my hot hole. Jamie then got into position and while Ray straddled my face forcing me to eat and suck his ass, Jamie held me by the ankles and alternatively gently screwed me and rammed me. I was so open he was able to punch fuck me drawing his cock competely out - then pistoning it all the way in. He remarked that the muscles of my rectum were so relaxed that the hole stayed open and rewarded me by blasting a wad of cum deep into me. I shot my load onto my belly and we grabbed each other in a hot embrace.
"Any time guys" Ray joked as he left, "just pick up the phone, and I'm very discreet" We all laughed but we never had a 3 Way with Ray again. I think Jamie secretly resented not being the first to penetrate me. We did, however, have other 3 ways and he introduced me to many sexual delights. I was in seventh heaven and wouldn't leave Jamie alone. I suspect I tired him out as, a year later, I wakened to a "Goodbye and thanks" note and I wept for four days, - my first lover. I did recover however and the chance of a threeway always causes my dick to swell and I get that certain feeling, in my rectum.
Footnote: Jamie and I did meet a few years later and the sex was grrrrreat as always. Jamie's big dick and his passionate riding did spoil me. However. I did meet his equal on my first visit to New York and, my first black man but that's another story for another day (I've loved 'men of colour ever since')
I now live in Vancouver, Canada
The End
If anyone is interested in reading more of my TRUE adventures or wish to comment on the above please feel free to Email me: bute2@hotmail.com