Sex gay stories: Jessica’s surprise. Author: Sxc Jess. The story is including True Story, Anal, Bi-sexual, Blowjob, Boy / Boy, Consensual Sex, Gay, Hardcore, Oral Sex, Threesome, Transvestite Genres.
Sex gay stories: Jessica’s surprise
Author: Sxc Jess
My dream that became a reality.
I have spent most of my adult life perfecting my feminine look, trying to develop my alter ego, Jessica, into a convincing, sexy slut. I’m 5’10” tall, slim build, long blonde which reaches the middle of my back and my best feature is my pert little bum and my long slender legs, which are silky soft with a golden tan due to my regular sun bed use. Now in my early thirties I have had numerous sexual encounters with men, of all shapes and sizes; some good, some bad and a couple of excellent ones.
I started my sexual exploits as Jessica by using Internet sites to advertise myself and soon ended up with a reputation locally. I even started getting guys who I hadn’t spoken to online contacting, because they were passing my number around and often guys would contact on the lunch breaks for a blowjob before returning to work. One guy in particular must of had me on speed dial and used me as his personal whore, not only would he pop round occasionally on his lunch breaks but would have me meet him while he was on a night out with his friends. He would either meet me in a pub car park or come to mine for a blowjob or a drunken fuck.
Probably my most memorable occasion happened when I least expected it to. It all started when I was 19, I had recently moved into my two bedroom flat and set my spare bedroom up as my little boudoir; the wardrobe packed with all my sexy dresses, skirts, blouses, shoes, boots, my dressing table ladened with make-up and perfume, a double bed and in my bedside drawers I had my silicone fake breast forms, lube, condoms and dildos. I took every available opportunity to indulge my fantasies as Jessica and became a part-transvestite, only living my male life at work and with friends and family, all other times I was Jessica.
Friday’s were my favourite day of the week, on returning home from work I would get out of my stuffy suit and have a nice long bath, while soaking I would shave every inch of my body. After my bath I would do my nails while having a glass of wine, however on this particular occasion I wanted to go for a little drive, therefore I didn’t have a drink.
I painted my nails a deep red colour, as I was feeling particularly naughty, after which I applied my make-up wearing; lipstick to match my nails, applied false lashes, plucked and shaped my eyebrows, applying foundation and blusher to my face, finally finishing my eyes off with a smokey effect. I gave my body a good spray with deodorant and perfume before styling my hair. I decided to straighten my hair and leave it down, most of it trailing over my shoulders and down my back but I left a few strands at the front, either side of my head which curved round my face and rested on my cleavage area.
It was then time to get dressed I was feeling so naughty and dirty there was only one outfit for tonight ‘the little black dress’, the dress hugged my figure so tightly it looked as though it had been painted on, the dress had a diamanté choker which secured around my neck as it covered my breasts, under my arms and was no longer than 2 or 3 inches past my crotch, my arms and back were all left uncovered.
To go with the dress I selected a strapless black bra and my tight black thong with a little pink butterfly on the right hip. I chose my sexy black stiletto shoes with a 4 inch heel. Firstly, I prepared my skin on my chest so that I could safely secure my breasts in place with the surgical glue, to negate any embarrassing moments (I learnt that lesson the hard way).
I then put my bra on before gluing my breasts into place. I then spent the next 5 minutes pulling and tucking my cock between my arse cheeks before slipping on my thong. My cock was only small when flaccid so it wasn’t too difficult to do, but for extra security I always wore thongs or knickers a size or two too small to ensure it didn’t fall out. I then slipped on my dress and shoes. To complete the look I added a pair of large, silver hooped earrings and a dainty, silver bracelet. I then spent several minutes at the mirror admiring myself and checking that I looked perfect.
Satisfied with my look I was ready to hit the town. I am very conscious when I’m Jessica and I am trying to leave my flat just in case I am recognised. So when I returned home from work earlier I parked my car round the corner instead of using the private parking for the flats. After checking that the Coast was clear I hastily made my way to my car and didn’t relax until I was safely in the drivers seat. My car was a little two seater, convertible MG sports car, the guys at work used to call it a “hairdresser’s car”.
It was the middle of summer and living on the coast the town was packed with holiday makers. By the time I made it to my car it was around 10:30 at night and it had just become dark. I thought I would firstly have a drive along the sea front because I loved it down there, to reach the sea front I had to drive through part of the town and I had done really well when until I was just about to hit the coast road when I was stopped by a red light.
Which was fine had the traffic lights not been right outside a pub with 4 drunks stood outside, one of whom was just in his boxer shorts and others tossing his trousers between them. They then saw me laughing and put the trousers on the bonnet of my car, I was shocked and willing for the lights to turn green as this drunken guy in his boxer shorts stumbled towards my car.
He managed to retrieve his trousers from my bonnet and was apologising. He moved away from car but the lights still wouldn’t change, “come on” I was thinking. Once the guy had put his trousers back on he kept looking over and waving, I gave him a little wave back and blew him a kiss as the lights changed and I drove away.
As I drove I thought about the incident at the traffic lights and felt content that they thought I was a woman. After an hour or so just driving through the town and along the coast, playing the incident over and over in my I had filled myself with so much confidence I was feeling bold or more likely stupid. I decide to find somewhere quiet to park and go for a walk close to the main pubs.
This was not a normal occurrence for me, because although I felt confident that people would perceive me as a woman, it was the fear of a drunken guy trying to chat me up. The reason being is my voice which isn’t particularly manly isn’t feminine either and would be a give away.
I managed to find a back street car park on the outskirts of the main drinking area, by this time it was around mid-night and there were lots of people on the street near the main pubs, as I drove past. It was around this time that people were leaving the pubs to either go to a club or make there way home. The car park was empty except for a couple of cars, so I checked my make-up, reapplied my lipstick exited my car and locked it.
I popped my keys in my little black clutch bag and looked up, it was then the nerves hit me, I felt so exposed in this dark car park with the only light coming from a single street light at the entrance. I took a deep breath and began to walk towards the exit, concentrating on my walk; walking smoothly, with my hips swaying from side to side, my head up for confidence and shoulders back. By the time I reached the exit my confidence had returned and I wasn’t having to concentrate on my walk, it was as if it was natural.
I decided to walk home and pick the car up in the morning, my flat was only about half a mile away and predicted it would take me around 45 minutes to walk it in these heels. As I walked the streets I was subject to a few lude comments, wolf whistles and cars tooting there horns, all of these filled my confidence I felt so sexy. I also saw a couple of domestics one which started because the guy was caught checking me out.
I had just entered my street when my phone rang and when I answered it was Steve (my regular who liked to meet in pub car parks). He asked if I was free to meet him because he had a surprise for me, I was a little perplexed but agreed to meet him. I told him that I couldn’t come back into town because it was too far and my feet were already beginning to hurt. So we agreed to meet in a nearby park, the park wasn’t far from my flat, however it was situated in a wooded area which I would have to walk through.
It took me about 10 minutes to walk to the edge of the woods, nervously I took a deep breath and walked along the path through the woods to the park. It was pitch black but for the full moon illuminating the park. The park is your basic park with swings, slides, roundabouts etc. I was the first one there so I sat at a nearby picnic table to wait for Steve, wondering what his surprise might be. I checked my handbag and made sure I had condoms and lube, never leave home without them.
I’d been here about 5 minutes or so when I heard laughter coming from behind me, coming down the path, between the trees. When I turned to look I could see the silhouettes of three men from the moon light, walking into the park. As they walked towards me I was able to identify Steve; he’s quite short for a man at 5’8″ tall but he was built like an ox, he was in his mid-40’s, with short dark hair and his face was always stubbly and worked as a gasman.
Even if the moon light wasn’t shining I would have been able to distinguish Steve because of his deep, husky voice, which sent shivers down my spine and made me so horny. Steve was wearing a pair jeans which were so tight on his thunderous thighs and forced his package to an enormous bulge at the front and a checkered shirt partly undone at the top. The other two I didn’t recognise, both in their late teens, early twenties, clean shaven with short brown hair. They were both over 6 foot tall and clearly hit the gym by their rippling muscles stretching their obviously, to small t-shirts they were wearing.
Steve greeted me “hello Jess, how are you tonight?” Just the sound of his husky voice nearly made cum. I replied “fine thank you”, he told me that he had been bragging about this little slut [me] who he would fuck on a night out and they have been asking to meet you, so here they were. He turned to the other guys and said “what do you think?”, they stood there rubbing their cocks through their jeans and nodded. He turned to me a asked what I thought to his surprise, unable to contain myself I stood up, threw my arms around Steve’s neck and began to kiss him passionately, our tongues massaging one another’s.
I felt his arms closing around my waist until his huge, shovel like hands rested on each of my arse cheeks. He began fondling my arse as he pulled me tight to him, I could feel his bulge growing, stiffening and hardening against my stomach. I was so engrossed in my kiss with Steve I’d almost forgotten about his friends.
When we finally broke I couldn’t see the other two, until Steve turned me round with his hands on my hips. He put one arm around my waist so his hand was on my opposite hip, while his other caressed my breasts, with my head tilted to the left he began kissing my neck. I looked at the other two guys who were sat on the table of the bench and stroking their exposed, hard cocks.
Their cocks were both thick, hard and at least 7 inches in length. As they slowly stroked their throbbing cocks the precum oozed out making their purple helmets glisten in the moon light. Steve whispered in my ear, which was just pure ecstasy to me and said “show me how much of a slut you are”, he subsequently let go of me and I walked towards those sexy, horny boys. I walked towards the first putting my hands on his knees and slowly sliding them down his thighs, all the time looking in his eyes.
Our lips met and we kissed for a moment, while he stroked his cock, I then slowly slide back up his thighs and maintaining eye contact before doing exactly the same with the second guy. This time I when we finished kissing I bent down towards his throbbing cock and reached my hand out towards the other guys cock. My hand was carefully guided to his cock and as I began to stroke his lubed pole, my lips reached the other guys cock. I kissed the tip and lightly licked his helmet, causing him to arch his back, moaning and pushing his cock towards my mouth.
I slowly began to suck his cock as jacked his mate, as my head bobbed up and down this throbbing pole I was bent over at the waist, with my pert little bottom sticking up in the air with my legs a yard apart and perfectly straight. After a little while I turned my head to engulf the his friend’s cock as I wanked him. As I bobbed up and down these sweet gorgeous cocks, I could feel Steve behind me, grabbing my waist with both hands and rubbing his cock against me.
After a couple of minutes I felt the bottom of my skirt being lifted up and exposing my arse. Steve pulled his cock from his jeans rubbed it between the cheeks of my arse. I was in heaven, being used as a slutty teen girl, it was making me more and more horny. This caused me to suck and wank Steve’s friends vigorously and they began moaning louder and louder. Every time I tried to change to the other person they would try to force my head back down on their cock.
I felt my thong being pulled to one side and my cheeks being spread, ready to take his length I was shocked to feel something soft, wet and flexible poking at my crack hole. It was then that I realised Steve was tonguing my hole. It felt so sexy I motioned my hips to synchronise with his thrusts. I began to moan with ecstasy so much I had to come up for air, throwing my head back and arching my back, enjoying every second of his tongue preparing my crack, while I wanked the other two. Steve then pulled away and stood up, pushing his hard cock against my crack, I could feel his hand on my hip as the other ran down my back. I heard him spit, then a huge dollop of phlegm hit my crack, just above my hole. He used his cock head to push his spit over my hole and massage it in.
By this time I was sucking the other guys’ cocks again, trying to swallow every inch, gagging as I tried to take last couple of inches. Then I felt it, this huge bulbous head pressing against the entrance to my hole, my heart was pounding as the pressure gradually increased. Then without warning my hole opened and swallowed his whole cock, again I threw my head back and arching my back as I moaned in ecstasy and pain at the same time.
Steve held me close with hands, no thrusting just waiting until my hole fully surrendered and accepted his raging beast. Steve u clipped my choker and the front of my dress fell away, it then felt like a hundred grabbing my breast. Steve grabbed my hair pulling my head back and said “I want to hear you scream bitch”.
With that he slowly pulled his cock out, so only the tip was engaged with my hole, he still had my head pulled back by my hair and I had a cock in each hand. I could hear the other two laughing and goading Steve “go on Steve, fuck her tight snatch, make this bitch scream”. Without a second to spare he pulled my hair hard as his beast furiously through me until his hips slammed into my cheeks.
I screamed with pleasure and squeezed those cocks hard. I sighed as Steve drew back again and again he slammed it deep into me, forcing the girlish scream from me. My head was then pushed onto the nearest cock as the pounding from behind me came thick and fast.
There were hands all over my body groping, squeezing, pinching, pulling. My arse and mouth were numb from the constant sucking and pounding. Steve fucked my arse hard pulling me onto him with every thrust, each time I let out a muffled moan, muffled by the throbbing cock in my mouth. After 10 minutes or so Steve began thrusting harder and pulled my head back by my hair, again causing me to arch my back.
I could feel his rock hard cock pulse as he shot his first load deep inside me, he drew back and thrust again as his cock shot a second load of cum. He did the same again as a third helping was injected deep into my arse. He then held me close, groping my breasts and kissing my neck as his cock pulsed and pulsed squeezing the last few drops from his cock. Eventually he relented and pulled out as one of the others took up his place behind me.
There I was bent over, tits and arse on display with two sexy guys one in my mouth and the other fucking me from behind as if his life depended on it, when all of a sudden there was a flash of light. I looked over to see Steve taking pictures of us.
I was pumping and sucking the guy sat on the bench, who by this stage had removed his top and was laying back on the table. I maintained eye contact with him as I sucked and gagged on his cock, his ripped torso glistened and looked so sexy in the moon light. My hands explored his body as my mouth slide up and down his cock. At the same time his friend was hammering away at my crack, his hands firmly around my waist. His cock felt huge inside me but slide in and out with ease with Steve’s cum providing the lubricant. He maintained his fast rhythm even as his cum was pumped inside me, mixing with Steve’s cum. He gave me a nice hard spank before as he pulled out.
One guy left, draped over the table of the bench I climbed on top of him. I straddled his cock which slipped inside me with ease, I slide my hands over his sweaty torso until our lips met. I could feel his cock throbbing inside me as we kissed and his hands squeezing my arse cheeks. After a minute or two I placed my hands on his sweaty, firm chest and pushed myself up, I began to ride his cock and he began grunting moaning with pleasure.
His hands firmly on my waist as he started thrusting into me which caused me to scream with pleasure. After a short time he sat up so we were face to face once more, as we kissed and our tongues thrashed about I wrapped my around his neck. As we kissed I ground my arse on his cock, which was still buried deep in my crack and he hooked his arms under my legs and grabbing my arse cheeks.
He then, with ease, lifted me up so that he was stood with my arms round his neck and my legs handling over his arms, suspended in mid-air he began pounding my arse. Each thrust felt like it was powered by a juggernaut. Sweat was poring off him and I was struggling to maintain my grip around his neck, however I soon felt his explosion deep in my hole.
Once he lowered me to my feet he began putting his cock away, the other two had already sort themselves. I was stood in this park with my dress rolled up round my waist, my bra and thong all wonky and cum running down the inside of my leg as the three guys say “thanks” and walk out of the park. Feeling used I redressed myself and collected my bag as I slowly walked home, savouring the feeling of my arse filled with three guys cum and recalling my time in the park. I was totally oblivious to the walk home the next thing I remember I was putting my key into the flat door.