Losing My Cherry

It was 1996 and I was living on the coast of Mississippi. I had been married for six years, and my second son had just been born. I had just returned from several months at sea on a Navy ship. My wife was always exhausted and not interested in sex. I, on the other hand, had a perpetual hard on. One day while driving along the beach I happen to notice a sign that said XXX 24 HRS. I was curious because I'd never been in an adult store before. On a whim I decided to see what it was like.

As I entered the store there was an array of adult material including movies, magazines, pictures, lubes, and toys. I was in awe. I immediately went to the magazines and started flipping through one that looked interesting. I had never seen one like this. The magazine had actual penetration shots. I was hard almost instantly.

I browsed through several magazines and made my way into the movie section. There were movies of all kinds from mild soft porn to some of the hardest porn I'd ever heard of. There was bondage, anal, double penetration, lesbian, gay, bisexual, and something I had never seen before, tranny sex. I couldn't believe how good the trannies on the box looked. If you couldn't see their cock, you would swear they were actual women.

I couldn't believe I was actually getting hard looking at a chick who had a cock. I had never even seen a tranny before and never considered sex with another man, but, here I was getting hard looking at men who had to tits. It's not like they looked like men, especially since they were all gorgeous. I really wanted to buy a movie but I was embarrassed to take it to the counter because it was a tranny flick.

After about 20 minutes of browsing the movie section, I walked to the toy section. Walking down the aisle I could see there were many dildos, vibrators, life size dolls, there were harnesses, and all kinds of things I'd never seen before. I couldn't believe there were so many sex toys. I mean, I had seen some before, but I didn't realize there were so many different toys. I had always thought I was experienced but apparently I was wrong.

I was getting ready to leave when I noticed a sign that said "booths" with an arrow pointing toward the door. I realized this must be where you can go watch movies. I looked around and no one was watching me so I stepped through the door into a dark hallway. On both sides of the hallway there were doors, each with a small red light above, some on and some off. I started walking down the hall and noticed several men standing near the back. I went into the first room I came to that had an open door.

The booth was somewhat small, only about 4 foot by 4 foot. There was a bench built in on one wall and on the opposite wall there was a TV monitor built into the wall. Next to the TV there was a bill acceptor and a coin slot. There was also a button marked up and a button marked down. I reached into my pocket and pulled out $2.00 and fed them into the machine. The screen came to life and in front of me I was seen a porn of two men fucking a woman. I thought, wow, this is really cool.

After watching for about 30 seconds I pressed the up button and the movie changed. I scrolled through several channels and stopped when I saw a chick with a guy sucking her cock. It was just like the videos I was looking at earlier. I couldn't believe it. If she had had clothes on, you would never know she had a cock. She was really hot. I realized that my cock was hard and was starting to hurt. I reached down and adjusted my cock. I wanted so badly to stroke my hard on but I was not sure if I should. I mean, I was still a little bit scared because this was all so new to me.

After about 5 minutes of watching the shemale getting a blow job, I decided to leave. I stepped out of the room and headed straight for the exit without looking around. I was sure that someone would recognize me, so I wanted to get out of there fast. When I reached my car my heart was pounding so fast I thought it was coming out of my chest. I knew I would be back, but it would be when I had more time.

Over the next several weeks I visited the store several times. Each time I went in I would browse through the store before going into the booths. Each time I went into the booth I would scroll through the movies until I found a movie with a tranny in it. I could not believe that I, a straight married man, was watching chicks with dicks. On the third or fourth visit I finally got the courage to pull my cock out and stroke it. I couldn't believe how hard I came. Immediately after cumming, I zipped up and left the building.

Each time after that I would stroke my cock while watching tranny porn. I guess you could say I was hooked. I just couldn't get over how good these trannies look in these movies. While watching the movies I began to imagine it was me in the movie. At first I started imagining it was me on my knees sucking a tranny cock. Then I started imagining that I was the tranny. I began to wonder what would be like to be sucked off by a man and what it would be like to suck a cock.

Every time I went in the store and went into the booth area I would go into the first available booth. One day I ventured further down the hall and went into one of the last booths. Upon first entering, it looked just like the rest of them. I put money into the machine and scrolled through until I found the flick I wanted to watch. After only a minute of watching I pulled out my cock and started stroking. I had plenty of time this day so I was just lightly stroking so I would not cum too fast. After about 5 minutes of stroking I noticed something out of the corner of my eye. I looked over and there was a finger sticking through a hole in the wall.

I was surprised because I had never heard of anything like this. I started to zip my pants when I heard a man whisper. I wasn't sure I heard him correctly. I thought he asked me if I wanted a blow job. I leaned closer to the hole and he whispered again 'put your cock through the hole and I will suck you off '. I wasn't sure what to do. Here I was a straight man watching a tranny flick being asked if I wanted a blow job by a man. He stuck his finger through the hole again and began bending it like asking me to come here.

I was somewhat reluctant to put my cock through a hole in the wall. What if the man on the other side was a psycho. He could cut my cock off and I would die of humiliation. After about another minute I saw movement again and looked down and there was a cock sticking through the hole in the wall. I couldn't believe it. A man in the next booth had stuck his cock through the hole apparently expecting me to suck it. I got scared, zipped my pants up, and left as quickly as possible.

As I drove away I could not believe what had just happened. I was both excited and scared. On one hand, here was a new experience and I was seriously thinking about doing it. On the other hand, what if someone saw me and recognized me and knew what I was doing in the booth. I resolved that the next time I went I was going to visit the same booth and at least get a blow job if it was offered.

It was about a week later and I had found about 2 hours to spend at the adult bookstore. Today was the day that I was going to go further than ever before. I was going to try to get a guy to suck me off. It felt like everyone was watching me as I walked in the store. It was as if everyone knew what I was there for. I almost turned and walked out the door, but I knew if I didn't do it today, I probably never would.

Instead of browsing around the store, I walk straight to the booths. If I was going to do this, I would probably need as much time as possible to get up the nerve. I went straight for one of the back booths. I went in the same booth that I was in the last time. I had decided before I got here that I was going to stay in the booth for long period of time. I immediately put $15.00 into the machine. The screen came to life and I found a good tranny flick to watch. This time I didn't wait, I immediately unzipped and started stroking my cock. I guess that was the right way to go because within a few seconds I saw finger comfort the hole. I was shocked that it was so quick. I began to have doubts again, wondering if I should be here at all. Another few seconds of thought, wondering what would happen, and I decided to go for.

I turned towards the wall and tentatively put the head of my cock near the hole. I heard the man on the other side of the wall say 'oh yeah'. I moved closer to the wall and as my cock entered the hole I immediately felt a wet warm sensation enveloping my cock. I couldn't believe it. My cock was in a man's mouth. I never imagined myself in a situation like this. The mouth on the other side of the wall was very wet and very warm. It felt amazing. I couldn't believe that I hadn't done this before.

I could hear the man on the other side of the wall sucking my cock. The sounds were unmistakable. There was a wet squishy sucking sound just like a couple of times when a girlfriend gave me head when I was younger. It was different because it never felt quite this good. The man on the other said the wall obviously enjoyed what he was doing. He was giving me the best blow job of my life. In less than 3 minutes I was already closed to cumming. I didn't want to cum this soon. I still had over an hour left and wanted to enjoy myself as much as possible.

I reluctantly pulled my cock back through the hole and I heard the man moan. I immediately saw his finger come through the hole again like he wanted me to put my cock back through the hole. I step back and made a quick decision. I knelt in front of the hole and whispered for him to let me suck his cock. I couldn't believe I had just asked a man to let me suck his cock. I watched as the man in the next booth stood up and approach the wall. His pants were around his knees and I could see his cock was already hard. He stepped forward and placed his cock through the hole. It was now or never.

I reached out and took the cock in my right hand. It felt strange, different than mine, and yet the same. His cock was larger than mine, and felt very warm and hard yet soft at the same time. I stroked it a couple of times and a drop of precum appeared at the tip. I leaned forward and placed the head of his cock on my tongue. I tasted precum for the first time in my life and allowed his cock head enter my mouth. My lips closed over the head of his cock and I heard him moan. I couldn't believe it, I was actually sucking a cock.

Once I had his cock in my mouth I decided to give it my all. I started moving my head back and forth taking his cock in as far as I could get it. He was long, but not very thick, and when I went down I started to gag. I was new in this so it took me several minutes to learn how far down I could go without gagging. I was enjoying sucking cock and actually hoping that the man on the other side of the wall would cum in my mouth.

I was really enjoying doing this. After about 10 minutes of sucking his cock, he pulled his cock out of my mouth and through the hole. This time I heard myself moan. I was really looking forward to tasting his cum. I couldn't believe I was thinking this. Just an hour before I was debating whether to let a guy suck me. Now I was on my knees hoping a man would shoot his load in my mouth. The man knelt down and asked me to let him suck me again. I stood up and put my hard cock through the hole. He had his mouth at the hole because my cock slid directly into his warm wet mouth.

Again it felt better than anything I had ever felt before. His mouth was so warm and soft and went it was like sliding into a pussy with a tongue. I knew I would not be able to last very long. In fact, I was already on the verge of shooting my load. I heard myself moan and I knew if there was someone in the hall they would be able to hear me as well. By this time, I really didn't care. All I wanted was to be able to shoot my load. I didn't care if everyone in the building knew I was getting a blow job.

After about two more minutes I moaned very loud and felt myself cumming. I came harder than I had in years. The man on the other side of the wall never took his mouth off my cock until I finished cumming. I don't know if he swallowed, but he sure as heck did let me cum in his mouth. I was sweating and breathing very hard. My legs were weak and I really needed to sit. I turned and sat on the bench and looked at the hole. After about 30 seconds I saw the head of his cock stick through the hole. Before I could reach it there was already cum shooting out of the end. The cum pooled up on the floor below the hole and I felt sad that I didn't get to taste it.

When the man was done I heard the door to the booth next to mine close as he left. I stood and zipped up my pants and left the booths shortly after with a porn still playing on the screen. As I left the building it felt like everyone was watching me. I didn't care anymore, and I knew I would be back as soon as possible.

It was just a couple days after that that I decided to go back to the bookstore. I had finished the job I was working on at the time, and knew that I had about 2 hours to play. I drove directly to the bookstore, not worrying about being seen, and parked near the back. Upon entering I went directly to the last booth. I knew from my last experience that this booth was sure to be active.

Within a minute after I walked into the booth I heard the booth door next door open and close. I inserted a $10.00 bill into the bill feeder. The screen came to life and I quickly chose a gay porn. I quickly took my pants off as well as my shirt and soon stood in the booth completely naked. I wasted no time and just knelt in front of the hole in the wall and placed two fingers on the edge of the hole. I watched through the hole as the man and the other booths inserted money into the slot and chose a gay flick.

It only took about ½ minute for him to have his pants around his knees. He stroked his cock for a few seconds and turned and approached the hole in the wall. His cock wasn't even hard yet but he placed it through the hole anyway. I immediately started sucking the tip of his cock and was amazed to feel it grow in my mouth. I could really get used to this. The feeling of his cock enlarging in my mouth gave me a sense of power and I decided I wanted to do this more often.

When the man was fully hard I started to bob my head up and down on his cock. I let saliva run out of my mouth all over his cock and I knew it had to be dripping down to his balls. My chin was soaked and dripping. I was trying to get as much of his cock in my mouth as possible. This man's cock was not huge but it was about 2 inches longer than my six. Not real thick so I was able to take it in my mouth without much effort. I was beginning to truly love the feel of a cock sliding on my tongue. I knew right then that I was what was termed a bottom.

As I was sucking I could hear the man moan on the other side of the wall. I could tell from his moans that I was doing a fairly good job. I was sucking is cock like I could imagine someone sucking mine. I was trying to make him feel good by doing the things that make me feel good. After about 5 minutes of sucking I decided I wanted to try to get this man in my throat. As I went further down on his cock I encountered the wall. There was no way I was going to get him in my throat through the hole.

I decided to be bold and pulled his cock of my mouth. When he pulled his cock through the hole in the wall I whispered to him "how about if we get a private booth together?" He said OK and gave me a booth number to go to. I quickly left the booth I was in and headed to the booth that he told me to go to. I was only in there for about 30 seconds when he stepped in with me. I could not believe the size of this man, he was easily 6 foot six and very well built. I am just 5 foot eight so he dwarfed me.

When the door was locked he turned to me and unzipped and unbuttoned his pants and let them fall to the floor. Without even being asked I dropped to my knees and as he put a couple dollars in the machine I engulfed his cock in my hot mouth. I gave myself a couple of minutes before I started to get him in my throat. The first few times I tried I gagged a little. He realized what I was trying to do and placed a hand at the back of my head and the next time I went down on his cock he pushed hard and forced his cock down my throat. I didn't have time to gag. I cannot believe I had half of this man's cock down my throat.

I was ecstatic, only the second time I had a cock in my mouth and about 4 inches of it was down my throat. No one had ever deep throated me, but I wanted this man to really enjoy my blow job. He held me there with his cock in my throat for a few seconds before he let up pressure and allowed me to bring my head back out. I immediately went back down and this time I took his cock in my throat on my own. I continued this action of bringing my mouth all of the way off his cock and then driving is cock head down my throat. I was so hard I couldn't believe it. My cock felt like it was ready to explode and I hadn't even unzipped my pants yet.

After a few minutes of my sucking and deep throating him he pulled out of my mouth. He told me to stand up and when I did he said " I really want a fuck your tight ass!" I wasn't sure if that was what I wanted, I mean, I had thought of it, but I wasn't really prepared for that today. I told him I couldn't because I didn't have any condoms. And he told me he had condoms and lube and he would make sure that it felt very good.

As we were talking I hadn't realized he was undoing my pants. Suddenly I realized that my pants were by my ankles. He was stroking my hard cock through my underwear. He reached inside my underwear and was rubbing my cock and balls with one hand while the other hand reached in the back of my underwear and was rubbing my ass. He was making me feel so good so I decided what the heck, and I told him that as long as he went slow and promised to stop if I told him to that I would let and fuck me.

I couldn't believe I just told a man that he could fuck me. I was standing in a small booth in an adult bookstore half naked while another half naked man slipped a condom on his cock and was preparing to fuck my ass for the first time. I was excited and nervous at the same time. I had not come here today with thoughts of being fucked, but now that it was about to happen I felt more turned on than ever. I only wish that I could have a camera to take a picture of my face the moment his cock entered my ass.

He turned me away from him and told me to bend some at the waste and lean on the wall in front of me. I realized this put my face right next to the screen and it was showing a close-up of a man's cock sliding in and out of another man's ass. I felt something cool and wet touch my ass then I felt a finger entering my ass hole. It was a little bit uncomfortable but not unbearable. This nameless man was sliding his finger in and out of my ass. After a few seconds it started to feel real good and I moaned a little. I guess this was his sign because he pulled his finger out and I felt something larger pressing against my ass.

I realized he had placed the head of his cock at my hole and was getting ready to slide it in and take my virginity. I felt the pressure of his cock head and then I felt my hole opening. There was a small amount of pain as the head of his cock spread my hole. I could feel the head spreading my hole and sliding into my ass. When the head of his cock was past the ring of my ass he stopped and let me get used to his cock in me.

As I stood there leaning against the wall with a cock in my ass, I couldn't help but think of how my life would never be the same again. The pain was already starting to go away and I realized my cock was as hard as it had ever been. I knew that when he started to fuck me I was going to enjoy it.