Kinky Sex Stories

Shemale Neighbor Sex Story

written by Ian

I moved into my new apartment down by the beach and the neighborhood was known for being somewhat gay friendly. I am not gay but the neighborhood is the only safe one in the area so it was either that or nothing. At first I didn’t even notice who was gay and who wasn’t but over time it became clear that I was one of the few single men in my building. There were lots of gorgeous women but they all assumed I was gay.

My neighbor that shared our balcony was a transsexual and she scared me at first. She was very forward with me from the start.

Hello neighbor, why don’t you come over and suck my cock so we can get to know each other”. Was the first thing Tonya said.

I told Tonya, the shemale, that I was straight but she thought I was just shy. She would love to sunbath her body out on the balcony and flaunt herself in her sting bikini. Then try and get me to come out and talk with her. I brushed her off at first but she was very persistent. I had to give her credit for that.

On a warm Saturday afternoon I checked to see if Tonya was on the balcony and when the coast was clear, I put on a towel and began to sunbath. I must have fallen asleep cause the next thing I knew was Tonya was rubbing sun tan lotion on my bare ass and back and legs. She was humming something about sleep baby boy sleep.

I was surprised to find that I had an erection.

“What are doing?” I asked Tonya.

“I am trying to make you horny so you will want to suck my big cock like you know you want to sexy neighbor.” Tonya said bluntly. “Is it working?”

“I thought shemales were supposed to me submissive and ladylike. “I said.

“Well sweety, I am a top. I like cut boys like yourself. I like to watch as they worship my body and most of all I like to……” she said

“Ok, ok, I get the picture here.”I said while stalling her so she didn’t find out about my hard on.

“Come on, you know you want to suck my cock sweet boy. It’s just a matter of time. I know you masturbate about me but your afraid. I like that. It’s very sweet and nice.” Tonya said.

“What about your boyfriend? Wouldn’t he be upset if he knew you were trying to seduce me?” I asked.

“Never mind him. He is not here but you are my beautiful little boy. Let’s make the most of our time together and give me a little kiss.” Tonya said.

Tonya leaned in to kiss me and I turned my head to the other side.

“What a bad boy you are. Making momma chase you so much.” Tonya said and gave me a spank on my naked butt.

“Ok, enough is enough Tonya. I’m straight and have a girlfriend and you are gay and have a boyfriend. And I’m not going to suck your dick ok? Now hand me my towel and let me go inside.” I said.

“Well aren’t we feisty? I tell you what sweetie, I am going to finish putting on your suntan lotion and then I will leave you alone if you want me to ok? There is no need to hurt my feelings. We are neighbors after all. Can I have a make up hug?”

“No Tonya, just finish what you were doing and then go alright?”

“Now that’s more like it.” Tonya said.

Tonya’s large strong hands began to work up and down my naked legs, thighs, ass, and back. I found myself oddly turned on by all this and it made me a little confused. I wasn’t gay, but I was turned on. It was a warm summer afternoon and Tonya had me very relaxed. I began to fantasize about what it would be like to suck her dick. And the more I thought about it, and the more she rubbed my back, the harder and harder my penis became until it was obvious that I was aroused my what Tonya was doing.

“See, I knew you would like it. But you hurt my feelings. I’m not going to let you suck my cock now. I am finished and you can go.” Tonya said.

“I am sorry I hurt your feelings Tonya. Thank you for the back rub. It was wonderful really. “ I said as Tonya left me there with my hard on.

The next day I saw Tonya sunbathing on the balcony and went out to talk to her. She asked me to put lotion on her and I rubbed her back and all over her body. She was really well built. She could have kicked my ass for sure. She was dark skinned and had a wonderful ass that I admit I would have like to fuck if it wasn’t attached to a cock and balls.

“Have you ever been with a man before?” She asked.

“No”

“Have you ever fantasized about being with a man?”

“No”

“Have you ever been attracted to a transsexual before?”

“Well, yes. One night in a bar I kissed a person who turned out to be a man.”

“Did you like it honey?”

“It was a little strange. I was surprised and scared by it. But I did find her attractive.” I explained.

Tonya turned over and said, “Be a good boy and do mammas front now.”

I tuned her over and saw her cock sticking out of her sting bikini. It was very large. Bigger than mine. I couldn’t help but stare at it for a few moments.

“I know you want to suck my play pole, but I am not going to let you. You are being nice to Tonya now but still, no matter how much you beg, you can’t suck my cock. So just forget about it.” Tonya said.

I laughed and continued to rub lotion all over her front. She had large breasts and her nipples were hard. I was fascinated by her and could not stop looking at her cock. She watched me and grinned.

Tonya invited me inside her apartment and sat me down and made some cocktails.

“Have you ever worn women’s clothes?” She asked.

“Maybe” I said.

“You should let momma dress you up. I can make you a beautiful little girl. It will be fun.”

“Maybe later.” I said.

Tonya and I had several drinks and talked about sex. All the sex talk was making me horny and then she led me upstairs to her bedroom and picked out some of her clothes for me to wear. I debated letting her dress me and figured what the hell. She stripped me down and then began to put panties, a bra, a skirt, a tight little blouse and stocking on. Then a pair of red high heels. Then she took me to her make up table and began to apply makeup and lipstick to my face.

I could see her 9 inch cock was erect under her sweat pants and began to stare at it.

“Now stand up pretty girl and lets walk about to get used to the shoes.”

I stood up and had a difficult time walking. I admit it was fun to be dressed in this way. She led me by the hand as we walked around the bedroom and I began checking out myself in the mirror.

“Now it’s your turn to dress momma as a man.”

I stripped off Tonya’s shirt, and then her tight sweat pants and then her panties. Her cock was huge. I then dressed her in my clothes. It was fun. We were laughing very hard trying to talk like each other. As we laughed, we embraced and our faces met. She learned forward and kissed ramming her tongue in my mouth. She grabbed my hips and held me like a woman. I was completely turned on and our cocks rubbed together. Both fully hard. It was a strange sensation. I was all mixed up on the inside.

Tonya took my quivering hand and led me to the bed and laid me down. She lifted up my skirt and pulled down my panties and began to suck my cock until I was about to cum. Then she lifted her hips over my face and inserted her large cock in my mouth. I sucked and sucked and sucked and soon she began to pump large amounts of cum into my mouth. I swallowed it all and then she inserted her finger in my ass and I came in her mouth.

What had I just done? I just sucked a cock. Sure, it was attached to a beautiful woman, but still. I was confused.

Tonya held me and started kissing me again. And again I became hard as she did too.

“What a good little girl you are. If you keep making me so horny, I am going to have to fuck you sweet little virgin ass. I know you want me to. But you have to ask me like a good girl.” Tonya said.

“Please fuck me. Oh pretty please. I will do anything you want. I need you to fuck me.” I said in my best girly voice.

Tonya took off my panties and lifted my legs with my high heels on them into the air and spread my legs. She rested her large cock on mine and kissed me deeply.

She inserted her finger in my ass and then the head of her cock. She began to fuck my ass and kiss me. She was fucking me better than I have ever fucked any girl. I was learning new things.

I came immediately. It felt amazingly good.

“Well, somebody really likes this. See I knew you were not straight, and just shy. I love my boys that way.” She said.

She kept fucking me until she was about to cum and pulled out and came all over my face. Ropes of cum on my makeup. I licked and sucked it all off.

We fell asleep together in the bed and in the morning she woke me up by inserting her cock in my mouth. I sucked her off and then she ran a nice warm bath for me and bathed me, dried me off, and put a string bikini bottom on me.

“Go out to the balcony and I will cook you breakfast and meet you there.”

I bathed in the warm morning sun contemplating what I had just done. Was I gay now? Perhaps it was just a one-time thing. Did I enjoy it? I think I did. Do I want more?

Tonya came outside with breakfast and champagne and placed me in-between her legs and spoon fed me. I was totally enjoying it. She was treating me better than any women ever had.

She began to kiss me and stoke my stomach until I was hard again. She undid the sting on my bikini bottom and bent me over and inserted her cock in my ass again. She began pumping and I came almost immediately again.

“I’m sorry Tonya. I am new at this and have not learned how to control myself.” I said.

“That’s ok sweetie, just let momma do all the work.” Tonya said.

Tonya fucked my ass until I became sore. Then she pulled out and came all over my back and rubbed her cum in.

“I have to go to work now sweetie, but when I come home, I want you in my bed and waiting for me wearing something from my closet. Do you understand?”

“Yes” I said.

Over the next month, I was Tonya’s bottom boy lover on a regular basis. I met her boyfriend a few times and he never suspected anything cause I had a girlfriend. My girlfriend met Tonya and they got along very well. Nobody suspected a thing. But we fucked and sucked each other as much as we could. I began to enjoy being fucked in the ass as much as fucking pussy. I also learned how to fuck Tonya in the ass too but she usually preferred to fuck me in the ass.

One day, My girlfriend came over without warning me and caught me on the balcony being bent up and fucked in the ass dressed like a woman. She got very upset and left. Later she called me and we talked.

“Are you gay?” She asked me?

“No. I am not attracted to men in anyway.”

“Well, why were you being fucked in the ass then?” Said asked.

“Well, it actually feels good.” I said.

“Why didn’t you tell me that and let me do that to you?” She asked.

“I am worried that you would think less of me.” I explained.

“No silly, I would have enjoyed it very much. Have you been sleeping with any other women?” She asked.

“No baby. You are the only women in my life and the thing with Tonya was just a one time thing.” I said.

“I have thought about this a lot. And I am going to try to forgive you. Actually, I am not that hurt by it because it’s not like I can ever give you what Tonya can. And I can understand that if anal sex turns you on, and you were afraid to ask me, then you would have to get it somewhere else. But now I know and I will give it to you. But you must promise to not sleep with Tonya again.”

I agreed and thanked her for her understanding. But soon Tonya seduced me again and I began to wake up with her cock in my mouth every morning.

Then Tonya’s boyfriend caught we one day. I was asleep in her bed when he came over and found me there dressed in panties and a teddy. He became very upset but also forgave Tonya if she promised never to do it again.

My girlfriend and I were having fantastic sex. She would sometimes use a strap on and sometimes dress me up. She loved it as much as I did. Then I would go home and suck Tonya’s cock and sleep with her. This went on for months until I began to feel guilty.

I told my girlfriend the truth and that I was sleeping with Tonya and I was feeling guilty. To my surprise, she told me that she fantasized about watching me being fucked by Tonya and asked if she could watch.

I asked Tonya and she agreed and asked if she could bring a friend to watch too. Why not?

Tonya’s friend turned out to be a handsome large black man named James. This made me very uncomfortable at first. Why had she brought James?

“You will see.” Tonya said.

So as Tonya began to bend me over and fuck my ass, and my girlfriend and James watched, James began to kiss my girlfriend. Tonya held me down so I could not get up. James started to undress my girlfriend and he slid his fingers inside her pussy. She was moaning, as my ass was getting hammered by Tonya’s beautiful cock. At first it bothered me but then it began to turn me on.

He bent her over next to me and we kissed side my side as James fucked my girlfriend in the ass, just like Tonya was doing to me. Tonya and James began to kiss. And soon, people were cumin all over the place.

First I unloaded as Tonya reached around and jerked me off. Then Tonya unloaded on my back. Then My girlfriend began to have multiple orgasms. Then James unloaded on my girlfriends back.

And then we all switched partners. It was like some kind of game of musical chairs. I fucked my girlfriend and Tonya and James began to suck each other off. More orgasms.

Finally, we all collapsed out of exhaustion. Tonya took my girlfriend upstairs for a shower and James and I sat on the couch. James began to message my back and shoulders and then started to rub my crotch. He turned my head to kiss him. I didn’t really want to kiss him but it was not so bad. He then pulled out his cock and told me to suck it. I did. I was not very good at giving head and James came in my mouth in under 5 minutes. Upstairs I could hear my girlfriend being fucked my Tonya. This made me very angry but James told me to calm down and relax and that it was ok.

I wanted to run upstairs but James grabbed me, pinned me down, and began to fuck me in the ass to shut me up. It worked. He was even bigger than Tonya. It was painful and I had to concentrate on relaxing my ass muscles to allow for his gigantic cock to penetrate me.

His cock was so big, I could not cum because each time I tried, my ass muscles tensed up and he just pumped me harder. It was starting to make me delirious, and then it began to make me feel incredible. It was like I was having multiple orgasms but unable to actually cum. I could hear my girlfriend moaning upstairs. Tonya was fucking her good. I began to hope they would continue so I could keep being fucked.

Soon, they came downstairs and found James pounding my ass. I was enjoying it so much that I couldn’t care less if anyone saw me or what. My girlfriend sat down to watch and gave me small kissed as I was being fucked. She also kissed James while he was inside me. Finally James came all over me and as he pulled out, I came too. Loads and loads of cum spewed out of my penis. I had never had an orgasm like that before.

Tonya made us drinks as we all relaxed.

“We have something to confess to you.” Tonya addressed me.

“Your girlfriend and I have been fucking each other for several months now and we wanted to tell you but we didn’t know how. We have fallen in love and wanted to have sex with you one last time before we told you.” Tonya said.

I was shocked. “You mean you are both breaking up with me?”

“Yes, I am sorry.” Tonya said.

“Well, I would have never guessed that.” I said.

“It’s just that I want to be with someone else for awhile. Watching you and James made me certain of it. I think you should be with a man.” My girlfriend said.

“I agree.” Tonya said. “Watching James fuck you, I could tell how much you enjoyed it. It’s ok baby. Sex is sex. As long as you enjoy it, then it doesn’t matter who it’s with.”

James leaned over and kissed me. I thought all this was very strange. On the one hand, I was being dumped and told I was gay. But on the other hand, they were right. James gave me the best orgasm of my life.

“Why don’t you just try if for awhile and think about it.” Tonya said.

James took my hand and led me upstairs into Tonya’s bedroom. He gently laid me down began to caress me and kiss me. It wasn’t so bad. He began to put a finger in my ass. I began to get hard. He began to put baby oil all over me and then he inserted he cock again. And just like last time, I could not cum because he was so large. I kept having multiple orgasms and began to moan and almost black out.

My girlfriend and Tonya opened the door and said, “I see you are in good hands now.”

Shemale neighbor sex story written by Ian.