As a teenager, I had a grown from admiring and jerking off to hot girls in porn, to slowly becoming jealous of them wanting to BE them, instead of wanting to fuck them. This fantasy grew into some experiments with lipstick, panties, and stockings during my later teens – but never more than that. However – everytime I jerked it to porn- i was picturing myself as a girl on her knees sucking dick and getting fucked.
one summer evening, my little fantasy got the best of me – I was slipped into the lace panties I had hidden in my room and pleasured myself watching a girl get fucked – pretending in my mind I was her.
After my session – I decided to go out to the bar with some buddies and forget about my secret slutty desires. After a few drinks I got bored with bar scene and decided to text a gay guy I had met a few days before.
Background – I met a guy who was a couple years older than me at my friends sister bday – she was friends with him. He started hitting on me that night but I was embarrassed and didn't respond. We did exchanged numbers tho – he wanted to maybe meet after the party to smoke a joint… I gave it to him… for the next few days he was texting me nonstop hitting on me as if I was a girl – it was so weird – he was treating me like I would text a chick I wanted to fuck! But i didn't really respond.
HOwever- this night I did respond – I asked him if he had a joint… He texted me back and asked if I wanted to come over. So I hopped into a cab and met him at his apartment. He offered me a beer and we chatted for a minute before he asked me if I wanted to watch a movie because he had no weed.
The tv was in his bedroom so we both lay on his bed and started watching the transporter. After about 5 minutes of laying next to him on his bed he touched my hand – I grabbed it and leaned over and we started to make out. This was my first time kissing another dude an it felt very weird- he was older than me and had stubble all over his face – I was starting to feel like a girl haha. After making out for a few minutes I started taking his clothes off and grabbing and stroking his dick. The next thing I did was start sucking his nipples an eventually I had made my way down to his dick which I started kidding and then slipping into my mouth and sucking. Can't remember how long I sucked his cock for but he figured out it was my first time and started talking about how slutty I was. At this point we started making out again with myself lying face up and him lying ontop of me- I then asked if he had a condom. He put on a condom and put some lube on his fingers which he then rubbed onto my hole and slowly fingered me for a few minutes. I was starting to moan a little at this point. Then I grabbed his dick and guided it toward my ass a lifted my legs up… He started to push the head of his dick in… It hurt so much at first – I was squealing like a little bitch so he held my hand, kissed me, told me it would stop hurting and pushed in harder… Eventually it was half way in… loosened up, moaned lifted my legs a little more up and squeezed them around his body- his cock pump all the way inside me and he really started to pound in and out of me hard at this point.
I was drunk and moaning at this point and was imagining myself being fucked as a girl – so I asked him to fuck me doggy style on the bed. I turned over and let him start fucking me from behind. When I started to push back on his cock he told me not to move and to let me fuck him. After a few minutes he pulled out, told me to stand up and bend over his bed- he then fucked me bent over. After this we got up onto the bed again, he lay down and I hopped ontop and rode his dick while facing him. At this point I was bouncing up and down and felt like a complete slut. I was riding him so hard he said he was going to bust. I slid off his dick and took the condom off – then I got on my knees and sucked his cock until he came in my mouth. I swallowed his cum and proceeded to put my clothes back on. He asked me if I wanted to be finished off – but I said no- I just wanted the experience of getting fucked like a slutty whore.
He then drove me home and I never saw him again. I jerked off on my bed 5 times after getting fucked like that. I just imagined myself as a girl getting pounded. I havent had a sexual desire toward a man since then…but the experiment of crossdressing is creeping into my head again…
Source: reddit.com/r/gonewildstories/comments/3ryp19/crossdress_fantasy_leads_to_popped_cherry_mm