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I would start off with my first sexual experience with a guy (which did not happen until I was 24), but that experience was subpar and did not end with a climax of any sort. At least, not a sexual climax; the guy became angry with me when I told him I could not suck his cock anymore and left, but not before letting me know that he should kick my ass.

Okay I will explain that one first. This was back when there were still Craigslist personals, before the days of Tinder and Grindr. I had recently admitted that I was gay (I now realize I am bisexual) to my then girlfriend/baby-mama, and we had split up shortly after. I was free to explore my sexuality at last and had my own apartment to host a willing participant. So, I was browsing through personals and decided to put up one of my own. It read something like this:

“Single guy, 24, looking to suck a dick. Can host.”

There were probably a couple more sentences, but I cannot remember what they were or might have been. I received an email reply within minutes from a handsome, tall, slim guy in his early 40’s. He had very short hair that was gray in some parts, piercing gray-blue eyes and some stubble. I provided him with my address and phone number, and he showed up within the hour. I remember being terrified when I saw him at the top of the stairs and walking towards my place, but also very excited to finally live out a fantasy I have quietly had since I was young (though I would not even admit to myself that I wanted it until I had come out).

I held the door open for him and he smiled at me as he stepped into my living room. I gestured to the couches and he took a seat. I sat on the other couch and tried to make small talk. The small talk lasted maybe 30 seconds to a minute before I knew I wanted to get this going right away. So, I took the plunge and asked ‘So, how big is your dick?’

He answered, ‘Well why don’t you come over here and find out.’

Oh my god, this is happening! I thought to myself as I got up, took 2 steps to stand right in front of him, and got down on my knees. With my hands shaking a bit, I reached out and fumbled with the top button on his jeans. I was so nervous that Ataşehir Fetiş Escort I could not, for the life of me, undo his jeans. He saw this and decided to undo them himself, then lifted his ass off the couch so he could slide them down to his ankles, along with his boxers.

There it was. The first cock other than mine that a man has decided to show me. I have seen other cocks in my life, but they were all incidental. This was with intent, and I could not wait any longer. With his cock right near my face, I knew there was no turning back (not that I would want to turn back any way). I leaned forward, grabbed his soft cock, and lowered my mouth onto it, taking the whole thing in my mouth in one swoop. I slowly bobbed up and down on the cock as best I could, trying to get it hard, and while I was sucking my very first cock he reached out to mine through my pants and began fondling me.

Normally, I think, this would not have been a problem at all. In fact, it would have added to the experience in a very good way, but not this time. I was very irresponsible with my sexual history and had contracted an STD a couple of years before. While this was happening, I had an outbreak and did not anticipate any reciprocation, so it threw me off guard. I did not want this guy to see my nasty looking cock as I knew that would be the end of it, so I took matters into my own hands.

I raised my mouth off his cock after a few seconds of his fondling and told him that I was so sorry, but I could not do this. He gave me a very angry, scary look, stood up, pulled his pants up and while buttoning said ‘I should kick your fuckin ass’ while storming out of my apartment. I said that I understood and closed the door behind him.

See? Not that great of an experience. It did open that door for me though, and I was eager to suck my next cock. In that apartment, I hooked up with 2 other men (2 separate occasions) before I moved out, and they were fun. The experience I would like to tell here though, is far more exciting. It was the one time I bottomed for a shemale.

No, not a crossdresser, a shemale. She had D-cup tits and a 7-inch cock, and I Ataşehir Gecelik Escort found her the same way I found the other men: Craigslist personals. The ad was mostly in Spanish, but it had her phone number in it. I texted her and sent her a picture of my face, and she responded with her address and a message telling me to come over right now. Looking back on it, this was a stupid way to meet someone, very dangerous. But I did it, a lot.

Shaking with nervousness, I got in my VW Jetta and drove to her apartment, which was only about a 15-minute drive. I parked on the side of the rode just around the corner from where her apartment was, stepped out and locked my car, a bit worried that it might get stolen as this neighborhood was kind of ghetto. Pushing the thought back, I walked up to her apartment and knocked on the door. After about 30 seconds of nervous waiting, she opened the door wearing nothing but a towel to cover her tits and cock.

“Hi baby come in!” She said quietly and backed up to give me room to enter. I stepped inside and closed the door behind me, locking it. I turned back around to see that the towel had dropped to the floor.

There she was, my first shemale encounter. She was a few inches taller than me, Latina, curly hair and a couple extra pounds but not fat. She had her hair up in a high ponytail and was wearing pink lipstick on her thick, luscious lips. She smiled at me as she walked over to her bed (it was a studio), grabbed a red throw pillow with gold dangly tassels all around the sides, walked back over to me and dropped the pillow at her feet. She beckoned for me to drop to my knees on the pillow, and I did.

Now her cut, thick cock was pointing straight at my nose. I did not hesitate; I grabbed her cock with my right hand and engulfed it with my mouth, bobbing up and down feverishly while jacking her off. She smacked my hand away from her fat cock, so I held my hands behind my back and kept bobbing. It was pure ecstasy, finally getting to suck a shemale cock on my knees like a little bitch boy. I loved, I fucking loved it. After a couple of minutes of this, she put her hands on either side of Ataşehir Genç Escort my head and began fucking my face with vigor. I gagged a couple of times but did not give a fuck; this was easily the hottest experience I had ever had (still to this day).

After face-fucking me until tears were coming down my face, she demanded that I get up and go to her bed. I knew where this was going, so I walked quickly to her bed, removing my clothes as quickly as I could on the way, and crawled onto it on my hands and knees, arching my back and sticking my oh-so-ready ass into the air for her. To make it even more inviting for her, I rested my head on the bed, sticking my ass out even more.

Once she got her condom on and rubbed a little lube on my asshole, she gently and slowly started stuffing her beast of a cock into my ass. I had never had a cock in my ass up until then, and it hurt a little bit getting it all the way in. She was patient with me and took her sweet time, pushing one inch at a time, until her cock was swallowed by my ass. Then she sped up and started fucking my ass hard, stopping every few minutes to take her cock all the way out and tease me. This drove me crazy until I was begging her to put it back in and fuck me. I still masturbate thinking about the teasing, then the fucking, then the teasing again.

She did this for about 10 minutes, then abruptly pulled out, whipped the condom off of her cock and demanded I started sucking it. I did without hesitation, very eagerly. I was so turned on I felt like I was losing my grip on reality and was eager to do anything she asked. I crawled up to her cock and stuffed it in my mouth, remembering to let go with my hands to let her face fuck me if she chose to do so.

I must have been so nervous/delirious/excited that my cock did not get hard during this at all, and I did not notice until she was reaching for it for a possible 69. Once feeling that my cock was soft, she ordered me off of her cock and said “Ah, too bad. Maybe next time.”

I stopped what I was doing, embarrassed and a little upset that we were not continuing.

“Do you have 20 dollars?” She asked.

A bit surprised, I answered “No, I’m sorry.”

“Okay, then next time, you give me 40 okay?”

“Okay.”

I put on my clothes, said goodbye, and walked out of her door. There was no 2nd time, unfortunately, but God I wish there were. This was, easily, the hottest experience of my life.

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