I had the Urges and never went through with it...until now.
I was 17, not nearly ready for my first semester at college. I had a steady relationship with my now ex girlfriend and we had sex just about everyday. But every now and than i would catch myself masturbating for old men of free sex chatrooms....the compliments and such that i received made me feel good. I would on occasion dildo my self with whatever i could find when i had the house to myself. During my online escapades men in the area would offer to pound my virgin butt and a lot of the time i would be about to say yes and than exit everything and snap back to reality...but this time was different. After a trip to a beach notorious for its gay population i began browsing craigslist for men wanting sex. I had a very specific age bracket , no lower than 35....thats it. I found a 38 year old man who desired a cross dressing bottom, i had worn my moms thongs before but never explored Deep into the subject so i decided to take up the ad. He desired pics and so did I and before i knew it i was entering his address into my iPhone maps app. I arrived at his apartment after a fifteen drive and as the sound of my Altima beeped as it locked thats when i saw it...the door that has forever changed my life had been pulled open and from around the side of the door i noticed the hand waving in my direction. As i approached i felt my heart pounding as i told myself "this is, here we go". As i entered the doorway i was almost shaking especially because this was my first sexual encounter with a man, he gave his hello and mine in response we did not exchange names for privacy sake as he shook my hand and pulled me in for a hug, i felt his bulge pressing against me through his flannel pajama pants. As we walked up the stairs to his living room i turned around to see his 9 inch uncut cock flailing out of his pants...i could not restrain myself any longer as i immediately began to stroke it, i felt the blood rushing into his dick as i began to lube It up with my spit. I asked hi. What he wanted ,he lowered me by my shoulders until i was staring his monster in the eyes and i instantaneously moistened my lips and began to indulge on my first cock. It tasted so good and with every suck i took it only improved, i asked him to gag me a little so every now and than he would choke me with his long uncut dick. I had hardened him up rather well and he complimented me for my first blow job but he than told me i was ready for more. As i laid on the bed stomach up i opened my mouth and stuck my tongue out as i prepared to give my first rim job. His juicy rim tasted so good as i probed deep inside until my nose was crushed by his tailbone. He than turned and stared deep into my eyes as we jerked each others cocks and whispered in my ears " It is Time". He propped me up on his bed on all fours and began to slowly finger my tight ass, as he attempted to spread my ass open he decided something bigger should be used so he mounted me and gave one deep thrust Sending me into a loud cry as his sack slapped against my ass. As he pulled out he went to the closet and grabbed a ribbed latex condom and Ky jelly. He had me deep throat his cock before putting the condom on and he asked me if my ass tasted good and i replied "Not as good as yours". I beard the latex snapping back against his cock and the lube sent chills up my spine. It was happening i could not believe it, and i felt his cock dance around the outside of my lubed up hole and he drove it balls deep inside me and proceeded to ram me elephant style from behind. The tears ran down my face he pumped harder and harder. My face became buried in his pillows as he drilled my ass continuously denying all pleas to stop because he and I both knew how badly we wanted it. I felt his leg muscles begin to tighten up and i told him to pull out and take condom off as soon as that ring popped off the head he jammed his cock back down my throat and face fucked me until he released his load into my stomach. He pulled out and grabbed my hand, i asked where we were going and he sat me in his bath tub, i figured a bath perhaps but he had kinkier plans as his golden stream began to cover my body. I than cleaned up and he gave me firm spank on the ass and said thank you. As i walked out of his apartment i saw his waving his semi hard uncut cock at me and while i pulled out of the parking lot all i could think was i had a gay experience. The loss of my anal virginity had been taken and it felt so good.
I never did return to him again but i always gaze at his current Craigslist posts knowing that that dick took my virginity.
Since the encounter i had not had another sexual experience with a man and am back to my straight ways for almost a year now. I was happy to try gay sex and i thank the gay community for letting me fuck at,east once.
Remember to always where a condom no matter how much they fucking suck because one wrong move and you can catch some crazy ass shit...don't do it because it could be you. Also avoid drunk sex because that could lead to worse happenings.