panty fantasy leads to my popped cherry (mm) | 2016

background: throughout my teens I slowly developed a desire to experience sex as a woman. It started with some occasional crossdressing experiments trying on panties, bras, stockings and red lipstick whenever I could get my hands on some. I also began to picture myself as the girl whenever I was watching porn - I was mesmerized by the sexyness of a girl on her knees sucking cock and passionately getting fucked and a desire to experience this would begin to overtake me. I never acted on this fantasty till one night when I was 19 - and I had the house to myself.

I was at home alone one summer afternoon, wearing a pair of lace bikini cut panties, preening in the mirror and eventually getting off on imagining myself as a cute chick giving perfect head and taking a man's dick deep inside of me. once i snapped out of my fantasy I took of my panties, showered up, and got back to real life - out for a night of drinking at the bar with my buddies.

Now after a few hours of partying with my buds - it was nearing midnight and my mind was back to fantasizing about wearing panties and being a little bit of a slut. I needed to get that out of my head so I glanced at my phone and decided to text a guy that I had met about a week earlier at a friend's sister bday party- asking him if he wanted to smoke a joint.

Now this guy was 21 - and clearly interested in other boys - as I had initially met him at a friends older sisters party. That night he was hitting on me all night - to which i resisted - but eventually gave him my number using the excuse that we could smoke a joint later that night. We never did meet up that night- but he texted me the next morning asking if I would "come over and keep him company in bed ;)". I was shocked - he was hitting on me as if i was a chick he was trying to fuck . It was weird but made me feel strangely excited and almost vulnerable - I didnt respond until the night I was out with my buds.

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 and we started to make out. This was my first time kissing another dude an it felt very weird. My skin was totally smooth and he had rough stubble - I actually started to kinda feel like a chick kissing a guy and starting getting extremely turned on. After intensely making out for a few minutes I started unbottoning his clothes - feeling his stomach and eventually working my hand down and grabbing his dick- which was rock hard and quite a bit bigger than mine. The next thing I did was start sucking his nipples an eventually made my way down the bed and had was facing down staring at his throbbing cock- which i instinctively kissed and placed into my mouth and started sucking and stroking just as I had seen girls do. I can't remember how long I sucked his dick for but I was losing myself in taking his shaft up and down my tongue and filling my mouth - I began panting. At this point we started making out again with myself lying face up and him lying ontop of me- and didnt realize that I was gonna go thru with next but asked if he had a condom anyway. Of course he did - and lube - He put on a condom and put some lube on his fingers which he then gently rubbed onto my assshole and started fingering me gently to loosen me. At this point I was panting hard and wasnt sure what was coming next - so I leaned down and grabbed his rock hard cock and motioned it up toward my hole... Then he grabbed my hands and kissed me - and started pushing his dick up my ass slowly - It hurt so much at first - I was squealing and he could tell - so he told me to relax and that he would stop if it hurt too much - but he kept pushing and pushing up insdie me.... I was begining to moan and squeal and he kept holding my hand and telling me how cute I was and not to worry. At this point I relaxed - let out an uncontrollable moan and let his cock slide all the way inside me - and then out again as he started to pump in and out of me missionary style- it hurt at first but then as loosened up it felt incredible, I told him how hot he was and to "FUCK ME!" in between pants and moans - i lifted my legs up and squeezed them around his body- he really started to pound me hard at this point.

I was quite drunk at this point so it was easy to imagine myself being fucked as an extremely horny inexperienced 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 dick 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 pounded my hole with 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 cock and took the condom off - then I got on my knees and sucked his cock until he came in my mouth. I felt the hot liquid fill my mouth - I didnt know what to do so 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 silly like a slutty whore.

He then drove me home and I never saw him again. I jerked off on my bed 5 times after grtting pounded like that. I just imagined myself as a girl taking it in the ass for the first time - I could feel it for the next few days. I haven't had any sexual desire toward another man or experience since then. This was 5 years ago now- I fantasize about doing it again - but dressed up in a few slutty items. ;)