Tags: BDSM, Sissy, Transgender, Adult-Youth, Anal, cum play, ATM, rimming, spanking, masturbation, blow jobs, first time, woods
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This is my very first submission and first work of erotica and was not edited by anyone as I'm afraid to share. If you are into this kind of stuff and would like to help me edit/improve also please reach out.
This story contains consensual sex between adults and minors that is completely fictional and does not condone any such activities.
Category: Gay, Transgender, Adult-Youth, Authoritarian, First Time,
Tags: BDSM, Sissy, Adult-Youth, Anal, cum play, ATM, rimming, spanking, masturbation, blow jobs, first time
This story is based on real events of my childhood but have been exaggerated and added to. The names are all different and I tried to keep to my original feelings and limitations. This takes place in my childhood which was a very long time ago in a time known as the 80s.
Basically watch stranger things and thats what it was like, no mobile phones, no internet, and a simpler time.
This all started out when I was 14, my friend Tom and I used to rent VCR tapes from a local place. Yes this makes me old and I still remember be kind rewind. The shopkeeper was probably in his 60s and looked like a dirty old guy. He knew us really well as we were there all the time as it was close by. Sometimes we were just looking at movies if we didn't have money to rent and he was always nice to us either way. One time Tom grabbed an R rated movie and while I didn't want to try it he said let's just see what happens. We put it and a nice PG move up and the guy didn't even bat an eye. From then on we just rented whatever we wanted without concern about rating.
Then one day we ventured into the adult section and grabbed a video cassette, pretty much the first we could see to get in and out as quickly as possible. The adult section was behind a curtain and was a dark little nook we were afraid of getting caught in.
We took it and another movie up and the old guy who just gave us a little wink, and checked us out. When we took it back we started watching the film right away we were so excited. We were rock hard before the movie even started and we started rubbing our cocks pretty quickly after is started through our pants. After a while my friend took his out, and I got a good look at it... It was very large and beautiful. I couldn't take my eyes off of it. I took mine out and was obvious that there was a very big size difference between us. I had a very small penis compared to his giant one. We played with our own cocks for a while and we went off to cum individually in the bathroom.
The next week we rented another adult film, and this one was a little dirtier as we took a little more time finding just the right one. We were a lot more comfortable when we started masturbating together, and I was looking at his cock more than I was looking at the film. I got up the courage and asked him why his was so much larger than mine, and what it felt like. He couldn't answer what it felt like, but he said I could hold it if I wanted to, so I reached out and grabbed his cock. It felt very different than mine, more spongy, and was very hot in my hands. I played with his cock for a little bit but then he told me that he really was only into girls and didn't want to do anything more with another boy so we just kept playing and finished up as usual.
The next time we went to go look at movies he said he was going to pick one out and for me just to trust him. When we got back he put the movie in and fast-forwarded it till it actually started. It looked like it just a normal straight movie with some cute petite women and big men. We were both really getting into it when one of the women in the movie took off their panties and showed that they had a tiny cock like mine. I almost burst right there I was so turned on. He asked me if I liked it and I said I really did and that they were very hot, but asked him if he also liked them as well. He said he really enjoyed it as well and had wanted to see this type of movie for sometime. He went on and said I would look like the girls in the movie as well if I put on panties and a bra, he had always teased me I looked like a girl because of my curly hair. I told him I'd love to if you had any for me to put on not really thinking it would happen. But he actually pulled them out because he had already taken a couple from his sister. He told me to go away and put them on and then come back only wearing them. I was a little bit taken aback but had said I'd do it so I went away and changed, I loved the feel of the silky panties and training bra and admired myself in the mirror for a while. When I eventually came back I felt very sexy but also very scared. He told me that I looked cute and that I should come and kneel in front of him and put my hand on his cock. I was turned on by him telling me what to do and I immediately followed his instructions. He kept watching the porn while I played with his cock and stared at it lovingly. After a while, he said I could put it in my mouth if I wanted. I reached out and licked the giant cockhead and started to kiss and lick it. I then tried to suck him and get it into my mouth which I tried to do but it was much too big for me to fit much of it in. I was inexperienced and not very good at all especially never having played with a large cock and not knowing how to suck a cock properly. Eventually he said, let me work my cock and he jacked it off telling me to just stay kneeling and watch him jack off. I stared as he worked his large cock up and down until he started to grunt and grown. He moved up and put his cock in my mouth as it started to come. I got my first taste of come straight from a cock and it was a bit much as it flooded my mouth. As I started coughing he pulled out and finished on my face. It was extremely exciting, but I was also nervous and didn't know if I did the right thing. He told me to go get cleaned up and changed, and I went to the bathroom and looked at myself in the mirror. I saw my face with cum dripping down my chin and splattered on my cheek still wearing the panties and bra. It looks so hot that I masturbated in the bathroom and came within seconds.
The next time we rented an even dirtier trans movie with more fucking, ass licking and cum play. We watched for a little while both playing with each other's cocks and getting very excited. He paused and said he had a surprise for me, he had taken not just panties and a bra, but also a short skirt and a blouse. He told me to strip down right there and put them on which I did gladly. When I was done, I look like a cute little girl. He was very turned on and told me to get down and start sucking on him again. I tried my best again. I could barely get 2 inches in my mouth and was doing all I could to imitate the girls on the screen. We had seen them not just suck cock but work the balls, the taint and even the ass. So he told me to start licking his balls, and then start licking his taint. I enjoyed this as was a lot easier than sucking on a large dick. He kind of pushed my head down further, and my tongue hit his asshole and I got a bitter taste in my mouth. I moved back up fairly quickly and he didn't stop me. After more sucking, he told me to get up and turn around, he raised my skirt and started to grab my ass and play with it. I really loved the sensation of my ass being played with. He started to get more aggressive and started to go deeper and start pushing against my asshole through the panties, which really turned me on. He then pulled down my panties, and started to play with my asshole for real. It was great, but he tried to stick his finger in, and that did not go well at all as there was no lube. We really didn't know any better as all the porn we had seen no one had ever used lube. They just stick their dicks in and it was all fine. He tried a little spit, but it was painful still. He then tried to pull me down onto his cock and his cock head which was slightly slick from pre-come started to enter a little bit into my ass. It was way too painful and just wasn't working so I told him to stop. He told me to get back on my knees and suck him more then which I started to do. He kept trying to get more of his dick in my mouth and I kept trying to help it but was not that great. We finished again with him masturbating and then shoving his cock in my mouth when he started coming. This time I was a lot more prepared for the cum to flush my mouth, and was able to swallow and take most of it.
Later on that evening, we tried the whole process over again, and he really wanted to fuck my ass but I told him that it wasn't working. I was really worried that my ass didn't really work that way and that maybe some people could do it and some people couldn't. I honestly really wanted to, but was afraid and didn't think it could work.. He was a little more demanding and rough that time. When I was sucking him he told me exactly what he wanted which was for me to lick his ass like the girls in the trans movie and held my head down when I got to his asshole. This time he kept it there and kept a hand on my head and told me to lick more. It was not my favorite thing and didn't taste great, but not as bad as the first time, and so I got used to licking his ass which he enjoyed tremendously. He was wanking his cock while I licked his ass then quickly moved down and came all over my face. He was happy but he was also obviously frustrated that he couldn't fuck my ass, and that I wasn't a better cocksucker.
It was a couple weeks later that we were able to meet up. This time, though we didn't have a movie and he had plans that he wanted me to do. He grabbed a whole outfit from his sister and told me to get dressed up in it. I asked him what we're gonna do and he told me to just get dressed and not ask any questions. I got fully dressed in the cute outfit and my cute curly hair really made me look like a girl. He told me that he wanted to go for a walk in the neighborhood with me dressed up like this. I was really nervous about going out, but he told me I had to do it if I wanted to stay friends with him and keep doing these things. He finally convinced me and we left his house and started walking. He lived in a very normal neighborhood with sidewalks and houses fairly near to each other but with nice parks and some wooded walking trails about a half mile from my neighborhood. I didn't know a lot of people in his neighborhood so I didn't feel too nervous about walking around. We clearly had a destination he was walking to which was a little ways away. We finally came up to a nice house back in a big lot and away from some of the other houses. It had beautiful gardens as we walked up to the front of it. We saw a nice looking old guy in the garden out front. When I look back on this, he was probably in his 40s and not really all that old. He said hi to my friend Tom, who he obviously knew and introduced himself to me as George. Tom introduced me as Susie his girlfriend. I looked at him, but didn't correct him. George said that he had a very cute girlfriend and he was a lucky guy. he asked if he wanted to go into his house and get a drink, which Tom said absolutely. So we went inside, and he motioned for us to sit up at his kitchen island on one of the barstools while he got out some lemonade.
George said that Tom had told him of our little problem and I had no clue what he was talking about. I asked him what he meant and didn't realize that we had an issue. He said that Tom told him about my ass being too tight, and that I was afraid to take his large dick, so we couldn't have sex. I was so embarrassed I turned beat red and I had no clue what to do. He said I shouldn't worry that he has helped many sissy boys like myself with this particular problem. He said, with the proper preparation, it would be smooth and easy, and would not hurt, he also said I would probably love it. I looked at Tom and Tom said please let him help. I was feeling very afraid and didn't really know what the proper thing to do was but with Tom and George both looking at me and asking me to do this I agreed.
George said the first thing I want you to do is agree to do whatever I ask you to do. He said just trust me and he wouldn't hurt me. He said that Tom had told him that I took direction well, and would be a good boy for him. He walked around the corner counter and put his hands on my back and started soothing me with a gentle rub. He moved lower and started grab my butt and massage it while I still sat on the stool. As he got more and more into my ass, I got more turned on. He asked me if I would be a good boy and do what he told me too. I said I would. He said then when you respond say yes, sir. And so I said, yes, sir I would. He told me to get up, and take my panties off and then sit back on the stool with my butt off the edge. I slowly said yes, sir, and got up and started to take my panties off. I was very embarrassed and scared, but also very turned on to be told so clearly what to do. So I got back up on the bar school and pushed my ass off the edge making my asshole fully exposed. He started rubbing my asshole gently. He got on his knees and started to lick my ass focusing on my asshole. Then he started to shove his tongue into my asshole, which is a whole new sensation for me and felt very good. All this time Tom sat watching intently as he licked my ass. After what seem like 10 minutes or so he got up and told me to stay where I was at. He went off and got some oil or lube and brought it back. He poured a good amount on my ass and started to rub it all around. He poured more on and started rubbing it around my asshole and very gently starting to put the tips of his fingers into my ass as he went by. He kept doing this for a little while until he started putting a little bit more and a little bit more in. He eventually got a full finger and was rubbing it back-and-forth and it felt great. when he tried to get a second figure and it started to hurt and I started to move. He grabbed my shoulder and said sit still boy, it'll feel good in a second. So I sat still and let him work it in. The second finger started to feel good and he asked if I thought I could take a third finger which I told him I thought I could so he put a third in and the pain returned but I held still, and it went away quickly, followed by pleasure. After a while of working three fingers in my ass, he pulled them out and told me to open my mouth which I hesitantly did. Then he shoved those fingers into my mouth and told me to suck on them, which I thought was very gross and fought against it. He pulled them out and spanked my ass hard. Hetold me not to resist him and be a good boy. He said he already knew that I licked ass and then I should get used to the taste. I was crying a little, but I managed to say yes sir, and he stuck them back in my mouth. Then he concentrated on moving his three fingers in and out of my mouth and told me to suck as he did so.
By this point, Tom had his cock out and was playing with it as he watched me get violated. George told Tom to crawl up on top of the kitchen island and position himself in front of me. He pulled his fingers from my mouth and re-oiled them and started working them in my ass again, I couldn't tell but he might have started to put a fourth one in as well but he told me the concentrate on sucking Tom off while he worked on my ass. He was giving me hints of how I could get more in my mouth and be a better cocksucker as I sucked, and he told me not to be afraid of gagging. I was working as hard as I could to get better and started gagging a bit, but kept going back to it. All the while my ass was getting worked on by George and it felt definitely like four fingers going in and out of my ass until I felt it go deeper. I didn't really know what was going on until I felt his pubic hair hit my ass, and I figured out that he was actually fucking me, I was shocked and very excited, but kept working on the cock in front of me. He told Tom to roll over and let me lick his ass so I started to lick his ass and again George gave me tips on how to be better. He told me to stick my tongue out and move my head back-and-forth so I fucked Tom's asshole with my tongue. He started to fuck me harder and harder and I the sensations overwhelmed me and I started to cum on the floor. Right after he started to grunt and came up my ass. He told me to get up and come to the couch where he bent me over the side of it and told Tom to get behind me. He then sat down on the couch in front of me and told me to start sucking him. And again I hesitated, because I knew he had just been fucking my ass. He slapped my cheek and told me to clean his cock or he would punish me. I put his cock head in my mouth and my ass and his cum mingled together and started to suck as much as I could. But I realized very quickly was that he was also smaller than Tom. Tom was aiming his giant cock right at my ass that had just been fucked for the first time.
When Tom started to enter me, it was an extreme sensation, some pain, but more pleasure. Tom was at least nice enough to go slowly and wait for a little bit once his cock was fully into the hilt. I assume George had given him some tips. So now my best friend is fucking my ass with his giant cock. And I'm licking clean the cock that had taken my virginity. Tom didn't last very long before coming in my ass. He pulled out and cum started flowing out of my ass. George told me to get up and go get on my knees and clean off Tom's dick as well which I did without hesitation. George came over and started pushing his dick in my mouth too. I could only get their two heads in my mouth, but we were having fun. Then George turned around and told me to lick his ass too. His ass tasted much better and cleaner, and so I got into licking his ass. He bent over to so I could go back-and-forth, licking Tom's ass and his ass.
George told me to go back on the stool and stick my ass out which was nervous about because it was fairly sore from getting fucked for the first time by two men. He came over and told me that I had been disobedient and didn't do what he told me when he told me to, and didn't say yes, sir, when he gave me a command. I apologized and told him I was sorry and that I would do whatever he told me and say yes sir. He said that he would give me a pass cause this is my first time, but that he had to show me a little bit what punishment would be like if I didn't obey. I wisely said yes sir and he started to spank my ass over and over again and I started crying while he was doing it but oddly enough was getting hard again. He spanked me just until my ass was red. He told me that this was just a sample and then if I disobeyed, he would spank me much harder and with a flogger.
He became more gentle after that and asked me how I felt. He wanted to know how my ass was doing and I told him it was sore, but I enjoyed myself and like the experience. He mentioned that he was a doctor and if I had any lasting pain to come back right away and not tell anyone else about it. He asked me if I had cum and I told him I had, and he saw the come all over the side of the kitchen cabinet. He said in the future, I would have to ask permission to cum, and I said yes, sir. He said as punishment for coming without permission and to earn coming next weekend that I would have to ask Tom if I could lick his ass at least two times next week. I hesitated again and so he said three times I guess and I said yes, sir before it became more. He said that I had to ask him when we were not having sex at random times and different locations. If Tom told him I had done this and licked his ass well, then I will be allowed to cum next week but I can't cum at all during the week. he asked if I understood and I said yes sir he told me to put my panties back on and head back to Tom's house.
We didn't speak much on the way back, but when he got into his house, he held my hand as we walked down to his basement. He said he was very happy that I could take his cock and that would be having lots more fun together. I smiled and said I was very happy to be able to satisfy him and that I would have to keep working on my cock sucking skills which he smiled and agreed. He told me that he loved how I looked, that I was super cute in girl clothes and that I would be a perfect sissy boy for him. That make me feel very happy and I felt I had accomplished something.
Next week at school on Monday we were between classes and going to bathroom together and I was pretty sure we were the only people in the bathroom so I asked him if I could lick his ass. He looked at me and took me to the big stall and locked the door then pulled his pants down. I got behind him on my hands and knees and started licking his ass. I licked up and down, swirling my tongue around his asshole and then shoving it in and out. The bathroom door opened and someone walked in and went up to the urinals. I froze and stopped licking but he tapped my head and then pushed it into his ass further. So I continued to lick his ass till the other kid left. He pulled his pants up and opened the stall and walked out of the bathroom. I closed the door to give me some time to reflect when I heard a flush from the far stall. I freaked out and sat as still as I could, I could see a little bit through the cracks and saw my English teacher walk up to wash his hands, he gave no indication that I was there and just left.
The next day was Tuesday walking home from school we passed by some woods with a walking trail and I asked if I could lick his ass in the woods.
He agreed and we walked down the trail a little bit to a space behind bushes and he told me that if I wanted to lick his ass I would need to take my pants and underwear off and put them on the ground to kneel on.
I was unsure but did as he said. He pulled down his pants just enough to show his ass and told me to get to work. I licked his ass for a bit before he turned around, pulled his cock out and started shove it in my mouth. I did my best, but gagged a bit as he kind of shoved it in my mouth deeper than I wanted. He fucked my mouth for a while, and then pulled it out started wanking it and came all over my face. He put it back in my mouth so I could suck the last come out of it and then pulled up his pants and left quickly. I was stuck there half naked, and with a cum covered face so I started to get up and I heard noise coming from a little bit away. I turned around and saw a guy with his dick out, wanking it and looking at me. He came over and told me to get on my knees again and then shoved his cock in my mouth. he pumped it a few times in and out and then started coming right away. I swallowed all of it and looked at it up at him and he said he'd love to do this again sometime. He then put his cock back in his pants and walked away while I got my pants on and used my underpants to wipe my face off and walk home. When I got home, I masturbated furiously while thinking of the events earlier.
The next couple of days, I was trying to ask Tom if I could lick his ass in safer places, and he kept saying no. It got to be Friday and we had agreed to meet on Saturday with George so it was my last day to get three asslickings in. I was desperate, I kept begging him all throughout the day at school, and he kept saying no. On the walk back, he asked me if I had sucked off the guy who was watching us which shocked me as I didn't realize he had seen him. I told him I had and I didn't think I had a choice in the matter. He said that's great because he's over by the trail entrance. I looked over and saw him and blushed. He was looking at both of us. Tom started walking over him and told me to follow so we went over. The other guy said that he really enjoyed our show from the other day and that he loved my sucking skills, which I still think we're not very good at this point. Tom asked him if he wanted to play with me again, and he absolutely said yes, so the three of us walked further into the forest area following the guy whose name we still did not know. He let us to a little private area that had a log in the middle of it. Tom told me to get fully undressed and put my clothes on the ground again so I had somethin to kneel on and something to put over the log. I was really nervous of doing this in front of the stranger, but he had already seen me half naked, but I never been fully naked in the woods before. I took off all my clothes, put them on the ground and my shirt over the log. They had already pulled their cocks out, and were playing with them, so I got on my knees and started to suck the stranger. I was going back-and-forth between the stranger and Tom's cock and was getting better by this point getting more of Tom's big cock in my mouth. The strangers cock was decent sized but not as big. Tom asked if the stranger had any lube, and the stranger said he definitely did and pulled it out of his pocket. Tom told me to get up and pulled me over to the trunk where he bent me over he asked the stranger if he wanted to fuck me first. The stranger moved over, poured some lube on my as and his cock and shoved his cock up my ass fairly quickly. It had been almost a week since I've been fucked and so it hurt a bit going in but at least wasn't sore anymore. While the stranger was fucking me Tom got in front of me, bent over and put his ass in my face so I could get my ass licking in, I thanked him and started to lick. The stranger kept fucking me and then started to grunt and fill me up with his cum. Tom told him to come around and have me clean off his cock with my mouth. The stranger said that was pretty dirty, but he was down with it and came over shoved his dirty cock in my mouth and made me clean it off. Tom said that if he liked having his ass sucked and licked, he should turn around and let me do that. So the stranger turned around, spread his big ass cheeks apart and backed up so my face was buried in his large ass, while Tom started to put his cock in me. This went on for a little while until Tom came in me as well. He pulled out and as the come dripped out of me he grabbed some of it and rubbed it on his cock then came over and had me clean his cock off without me knowing he had done that. I sucked and licked his cock clean, tasting both his cock, my ass and both of their cum. The stranger had his clothes back on by that point, and gave Tom a note with his number on it, and said he had some other friends that would love to use me.
Next chapter:
The next weekend with George and Tom, and a few other encounters.
Future chapters: movie rental guy (who I honestly got fucked by in the back of his seedy movie rental shop), Coach, English teacher.