Written by iluv2lick83
5 Jul 2013
dressing up for gf ends in first real gay experience
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Apart from some names being changed this is 100% true hope you enjoy.
I've always had and enjoyed an adventurous sex life but apart from a few experimental fumbles when I was young and receiving a blowjob from a guy years ago I'd never had a real gay experience, like most guys I've had a few fantasies about it but nothing more..... Well until last weekend!
To explain first I need to go back two weeks. My names Mark, I'm 29. My girlfriend Louise is 26 and like me is very adventurous and loves kinky sex. I often work away through the week so on weekends we can be like rabbits and nearly always film ourselves to watch through the week when we're apart.
Anyway, we got home Saturday night after a few drinks and was chatting about roleplay games getting excited about tonights ideas but Louise kept moaning how its nearly always her dressing up and that she wants to be in control for once.
As Lou had met me straight from work she said she was going for a quick shower and wanted me to join her, I said I would in a bit but had other ideas to surprise her.
Listening for the shower to start I quickly stripped naked, opening her lingerie draw I grabbed her favorite lace covered bra and matching French knicker set and a pair of stockings. Then looking through her 'dress up' bits picked her short tartan pleated skirt (my favorite for her to wear), white blouse and long black wig.
I'm only just over 10stone so apart from her large breasts our bodies are similar in size so I knew they'd fit ok. Needing to be ready before the shower turns off I quickly pulled on the stockings, strapped on and stuffed the bra, then started to pull on the French knickers.
WOW!! I couldn't believe how the lace felt against my skin and by the time I had them on properly I was so turned on and loving the feeling of them. Blouse buttoned up just above my 'breasts', skirt just covering my ass, wig in place I quickly applied some lip gloss and positioned myself on the chair, opposite I kept looking in the mirror amazed how hot I looked and really feeling horny as her shower ended.
Questioning why I hadn't joined her, Louise suddenly stopped mid sentence as she turned into the bedroom and just stared at me in shock. For a moment I thought id gone too far but then she just smiled and said "oh hi, what's your name?"
The next few hours were amazing together and got it all on film. (if anyone wants to know our roleplay just ask.)
Before leaving for the week I uploaded the new video to my PC and secretly pinched a pair of Lou's lace panties. Alone in my hotel room I'd wear nothing but her panties as I watched our latest vid, playing with myself as the feeling of the lace against my balls and ass drove me wild. We'd often have phone sex and Louise asked if id dress up again after her night out on Friday and wanted me to be a cheerleader and her the sports teacher. Turned on and thinking of surprising her a bit more I spent Thursday evening shaving and waxing all my body nice and smooth before traveling home Friday morning.
Sorry if that went on a bit but wanted to give a full explanation of how the rest managed to happen.
In the evening Louise went straight to Sarahs house to get ready for their girlie night out and my mate John, 34 (Sarahs bf) came to mine for a good drink session and a laugh while consuming some not quite legal substances.
As John flicked through the tunes on my laptop, after plenty of vodka and feeling high the usual bloke conversation of sex came up, like typical mates we've always boasted to each other what fun we've had and both perved on each others home made vids comparing notes. He asked if we had any new ones which I quickly denied dreading the piss taking id get if he saw it, saying Louise found out he'd seen old ones and refused to make anymore. With that the subject changed to something on Facebook and the drinking picked up pace.
Wasn't long until we was low on drink, so quickly taking in another line I headed for the shop down the road. With my mind constantly thinking about fun when Louise gets home, the powder making me even hornier and my growing cock rubbing against my jeans, I quickly bought the drink and rushed home.
Closing the front door behind me I noticed the stereo had now been turned on instead by how loud it was. Walking into the living room I almost burst into laughter... Sat with his back to me I could tell his hand was over his lap and his arm moving up and down as he let out a few groans.
Trying to work out if he was playing a prank or if he'd really not heard me come in, I went to shout to shock him but as I could now make out the laptop screen it was me who was shocked!!
I quickly turned out of the room, head spinning. He'd been wanking to me dressed as a girl giving Louise a lap dance. It was obvious it was me he was watching so there's no mistake.... Its got to be him winding me up. My thoughts got broken as John blurted out in broken breath "god that's hot". I looked in again, his arm going faster, face closer to the screen, he wasn't joking around, he was now watching on screen me slightly bent over, skirt revealing most of my cute ass, panties pulled to one side as Lou kissed and teased before tongue fucking my ass and John was loving watching it.
The shock by now had completely gone and I suddenly noticed how turned on I was. We've seen each other naked plenty of time but never before had any thoughts crossed my mind. It was like the drink, sniff, seeing the vid and especially seeing John wanking over it had put me on auto pilot as I crept upstairs.
Like I'd been possessed moments later without a thought I'm stood back behind him but closer than earlier and in the best girlie voice I could do "excuse me sir, I'm here for my detention"
John jumped, trying to hide his hard cock as he turned around his eyes widened when he saw me stood there in white knee high socks, mini skirt, fitted shirt stretched over my stuffed 'breasts', school tie and blond wig in pigtails. I felt so sexy as his eyes looked me up and down and his hand moved back to his cock.
"been as sir is enjoying watching the video of me how about a real dance?" I sheepishly said.
He got straight into character telling me how much of a naughty girl id been and if I wanted to get out of detention I had to do as he says. Walking over I began to give him a lap dance rubbing my tits and ass against him. As I teased his cock with my hips and looked into my eyes a sudden realisation of everything shot into my mind but before I could think anymore he started kissing me passionately.
I went down to my knees, taking his cock in my hand I started to lick all the way up the shaft and head before taking my first ever cock in my mouth. John let out a massive groan as I took it as deep in my mouth as possible building a good rhythm it didn't take him long until his warm cum shot down my throat, tasted so good as I tried to swallow it all as he faced fucked me.
"am I being a good girl sir?"
"your a naughty little bitch who needs to be punished " he grabbed my arms pulling me up and spun me around, bending me over the table, my ass peaking out of the mini skirt just infront of him. He gave three hard slaps to my right cheek sending a shockwave through my body. With a hand gripping each cheek and pulling my panties to one side he buried his tongue deep in my hole feeling amazing as it moved around inside of me, his hand reaching around, sliding inside my panties and began wanking me off. Feeling myself getting close to explode I tried to turn but he just pushed me back down, I couldn't hold it anymore John eating my ass was driving me wild making me scream out as I filled my panties and skirt with cum.
He continued licking away until my cock stopped twinging, then with one hand still pinning my hips down he brought his cum soaked hand to my mouth and ordered me to eat my juices.
Still trying to catch my breath after cuming so much I felt his big cock pressing against my tight virgin hole, with only his spit for lube I said there's no chance he's getting in me.
"did I give you permission to speak? you walk around school with your little skirts teasing all the boys, well now its time to get what you deserve!"
I felt the pain as the first inch went in but that was nothing as he grabbed my hips and in one push forced deeper in me, I almost cried with pain and felt like id pass out. John allowed me to recover slightly before pulling back and thrusting forward again.
With every stroke I could feel my ass widening as he goes deeper and deeper. The pain was still there but pleasure was starting to take over and I started pushing back against him. His thrusts started getting harder and faster and as I looked over my sholder I saw the orgasm building up in his face. I felt his cock twinge inside of me and then the wet feeling as he cum nice n deep to completely take my virginity.
He stayed inside of me for a few minutes, making me want more but both knew the girls could come home at any point. My ass felt strange as he pulled out but was soon replaced by his tongue as he licked and sucked my hole clean.
he said id been a good girl taking my punishment and after a passionate kiss I went upstairs to change back into my clothes apart from the lace panties and we carried on the night as if nothing had happened.