A Top No More

◦Hi. This is my first story here and my first language is not English. So I'm sorry for all the mistakes I'm gonna make writing this story:)

◦It was about three years ago.I was 22 and I was an engineering student and I had a part time job as a math teacher for students. I used to live in dorm but now that I had enough money I thought maybe it's finally time for me to get my own place. So I rented an apartment, not so big, but good enough just near university. Life was going good, I didn't have any trouble. I was in a good position financially, I was studying in my favorite field and I didn't have any problem with my sexual part of life. I'm john. I am 5' 8",not really tall but good enough in my opinion. My looks were good or at least okay. I have a bright skin and brown hair, and I didn't have that much problem getting girls numbers. I considered myself bisexual.

Although I was strictly top and attracted to bottoms. I used to bring girls a lot to my house now that I had a place of my own, but I never had any boys. Someday I thought maybe it would be fun to have a boy over once. I started searching in apps and met someone online. He was a 25, 5' 10" bottom and he had kind of a nice ass. We chatted for a while and finally we agreed to meet at my place. I was kinda nervous because I never really met anyone like this before. His name was mark and he was supposed to be here at 7pm. And we pretty much were clear it was just sex. Finally he arrived. I greeted him inside. He was fine and we started chatting for a little while but I really didn't know what to say. It was really new to me and to be honest I was kind of embarrassed for it. So after a while we really didn't have much to talk about and there was this awkward silence.

◦He finally said((so, should we get into it?)).

◦I agreed. He told me before that he liked to crossdress if it's okay and I really liked having sex with a crossdresser so i told him great why not. I showed him the room where he could change clothes. After a while he yelled((I'm ready)). To be honest I have never been this nervous about the sex even the first time I had it. This was really a new experience for me. So I went in. He was wearing nothing but thigh high. I kinda like it if he was fully dressed in women's clothes but this was okay too. We started. He laid there and I started massaging his ass. As i was doing it I realized i'm not getting hard at all. He had a nice ass and I've had done it with a guy before. I didn't know what was the problem. After a few minutes of massage

◦he finally said((ok ready to fuck me?)).

◦I replied((I'm not getting hard I don't know why)).

◦He said((well do you want me to blow you?)). I said why not. He did but still nothing. He then looked up to me and said

◦((well how do you usually get hard?)).

◦I told him this was the first time this happens to me. Maybe I can get hard by watching porn.

◦Mark said((ok so let's watch some porn. Do you have anything on your laptop or somewhere?)).

◦I said((no but we can watch online. Let me play one)).

◦I opened my laptop and went to a porn website and played a gay crossdressing porn so it could help me get into the mood. As we where watching the porn mark started to run my cock. But still nothing. We keep on watching for a few minutes and then I felt his hand on my ass. I was fully naked at this point by the way. I looked at mark ad said:

◦((what are doing?)).

◦He said((maybe this will help)).

◦I said((no I've always been too I don't like being bottom)).

◦Mark said((well at least let me do it for me. I've come all this way and nothing? I'm verse. I can be both. Just let me cum real fast. I don't even wanna fuck you just tubbing your ass and jerking off)).

◦I felt bad for him. He just wanted to have a good time and now I can't get hard. Finally I agreed.

◦((ok. But nothing more))I replied.

◦He said thank you and started grabbing my ass. Then he asked((can you get on fours in a doggy position. I can cum faster that way)). I said (( fine but just massage and jerk off nothing more ok?)). he agreed. I got on arms and legs on the bed. The he grabbed my waist and said((try to lower your waist and push out your ass a little. That's sexier)). He styled me and now I was in doggy styled position like a pro! He started to jerk off with one while massaging my ass with the other one. After one or two minutes I said((hurry up mark I'm getting tired)). He said((wow John you have a really nice ass did you know that? It's even better than mine man. You are not that hairy either I really like it)). I laughed and said((yeah whatever. Just get it over with and jerk off)). Then I felt a finger around my hole. I said((no no. No fingering)). He replied((oh come on it's just one finger. Please?)). I thought to myself if it helps him cum faster then why not. let's just get this over with. I told him((ok but be faster please)).He licked his finger and slowly pushed it inside my ass. I have never had anything in my ass and I guess was extremely tight. Because it hurt like mf. I said((ouch easy)) he said((sorry)). He kept fingering me. After a minutes he stood up. I said((did you cum?)). Mark said(( no I'll be back I need something. Be back in 5 minutes it's just nearby)). He wore clothes and went out and I laid on bed. He got back really fast with a plastic bag in his hand. I said((what is that?)). He said((nothing. Hey would you we are my thigh high? It bet it looks really sexy on you and I can jerk off and cum faster)). I thought to myself if I say no he is just gonna insist and what the harm anyway? So I said ok and wore his thigh high. I got into on all fours again with my butt pushed out.

◦He said((wow you really look good in that)).

◦He started playing with my butt. Then I felt like he was using two fingers because suddenly I felt a little bit of pain.

◦((What are doing mark it hurts))I said.

◦((You'll get used to it)) replied mark.

◦After a minute marked ordered

◦((I want you to do the work now. I keep my fingers steady and you push back to them))

◦I did as he told. It felt like he was kind of in charge now. Anyway i just did as he told. It was weird. I was practically fucking myself with his fingers. It wasn't as painful as it was before. he ordered me to stop and pulled something out of his bag that he brought. It was a lipstick!. He gave it to me and said

◦((here, put this lipstick on))

◦((What?no way mark))

◦Suddenly he spanked my ass and with a seriousness in his voice he said

◦((never answer someone with that tone when you standing in front of him doggystyle in thigh highs while hr is fingering your ass okay?))

◦I was kind of scared now. I didn't answer him and just took the lipstick and applied it to my lips. What the hell was that spank about?

◦After I was done he change my position so I was facing the mirror. I saw myself in the mirror. A small boy on his fours in a doggystyle position. With my red lips and soft brown hair while wearing thigh highs. He put his 2 fingers back in my hole and said

◦((ok baby continue))

◦I did as he said. I was going back and forth with his fingers in my ass. I did it for a while and I actually forgot how I ended up in this position and what was I doing. My eyes were closed and I was just going back and forth with the rhythm. Suddenly he pulled out his fingers of me and picked something from his bag near him. OMG it was a condom!

◦((Hey mark what are you doing?))

◦((I'm going to fuck you))

◦((What?no way. You are waaay over the line now))

◦Mark grabbed my chin and turned my face to the mirror

◦((Look at yourself. Look. A small boy on his fours in a doggystyle position. With red lipstick on his lips and soft brown hair while wearing thigh highs. And a guy has has put his 2 fingers back in your hole while you are fucking yourself with that. Do you really think you are a man? No man would let anyone do this to them. You are a sissy. I'm not even an alpha top and I did this to you))

◦While he was holding my face towards the mirror with his hand, he spanked my ass with his other hand. I let out a moan. He placed his dick at the entrance of my butt.

◦((Don't worry I have been a top too. I'm gonna make you beg for my cock at the end of the night))

◦I wanted to resist a little bit and tried to get myself free. But he held me in place with his hands on my waist. I looked at him with a begging face((please mark don't)). But he ignored me and pushed his dock a little bit into my ass. He spanked me once more and said((loosen up and try to relax. It will hurt less)). Then he suddenly pushed a little bit further and I felt the head of his cock in my ass. OMG! It was really painful. I screamed out of pain and he just rubbed my neck and my hair and said((sshhh baby relax. You'll get used to it)). He the pulled out his cock and did it again. There was a little tear in my eyes. He brought his face next to my ear and whispered((relax babe)) then he kissed my check and wiped my tears with his finger. He then continued to slowly push his duck a little bit further every time. After five minutes of that I got used to having his duck in me. I was still moaning out of pain but not very loudly.

◦((Aah. Easy. Gentle please. Aaahhh))

◦((are you better now Jennifer?))

◦((A little. And who is Jennifer!?))

◦((You. That's what I'm gonna call you from now on. It suites you better. Are you enjoying this?))

◦((Nooo. No way))

◦((Then why is your dick so hard and you thrust back every time I push my dick inside you?))he answered with a little laugh.

◦OMG! He was right. I didn't notice this until he mentioned. I got used to doing this with his fingers and now I was doing it spontaneously. mark said:

◦((now that you got used to it it's time for the real thing)).

◦Suddenly he started to thrust into my ass with a crazy amount of force I have only seen in porno movies. I started to moan.

◦((Uh...uuuuhhhh... please mark go easier.... Uuuuuhhhh))

◦((Shut up bitch you love this. You are leaking cum all over the bed. Ah god this feels so good. You have the tightest ass I have ever fucked. Uhh yes))

◦OMG I can't believe this! I was getting fucked in the ass in my own bed and I was leaking cum too. He was thrusting into my ass and I was just moaning. But I'm not sure if my moans are out of pain or what.

◦((Aahhh...uuuuhhhh...uh uh uh...))

◦Marked yelled as he was fucking my ass

◦((Tell me what are you doing Jennifer ))

◦I didn't answer. I couldn't. The situation was very intense for me I could hardly say any words. I just kept moaning. Mark slapped my ass and yelled again

◦((I said tell me what are you doing slut))

◦He really spanked me hard this time. I let out a night pitched moan and said((I'm..ahhh.. i'm being fucked..uhhhh)))

◦((Yeah that's right bitch. You are being fucked in the ass))

◦He kept fucking my ass. And I loved it!. Wtf is wrong with me??? I had never felt this amount of pleasure before. He said

◦((Do you want me to come in your ass?))

◦I didn't know what to say. It was too humiliating for me. Then suddenly he stopped moving his duck inside me and kept his dick still.

◦((OMG why did you stop?))

◦((I want to hear you say it))

◦I couldn't handle this anymore. I needed him to fuck me.

◦((Ok. I want you to cum in my ass. Pleaaase. Just keep fuckin me))

◦He said(( good girl)) and kept on fuckin me. OMG yes. I love it. I need it. After one minute he said

◦((I'm cumming. You ready Jennifer?))

◦I said(( uuuhhhhh... yes daddy. Please cum inside me))

◦he groaned and said((oh yeah. here it goes babygirl))

He started cumming inside me! I have been leaking so hard for the past few minutes and this finally pushed meover the edge to cum. I was cumming while a guy was filling my ass with his cum! After he calmed down from his orgasm he said

◦((Good girl. You came from being fucked by your daddy?haha. Good girl))

◦he rubbed my neck and my hair while he was saying that. Then he laid on the bed and pulled me closer to him. I gave him a kiss and put my head on his chest as his was running his fingers through my hair. He said

◦I told you I'm gonna make you beg me to fuck you babe:) ))

◦I laughed as I closed my eyes with a big smile...