Kinky Sex Stories

My First Time Anal Sex Story by Jewels Reveda

When I was a teenager, I was often overlooked by the guys at school. I was a nerd and a little bit of a free thinker. Guys usually made fun of my short hair and glasses. They were sometimes quite cruel to me. So when I went to college and found myself in bed with a woman one night and really getting off on it, I was not surprised to discover that I was a lesbian. In fact I was more surprised just recently to discover how much I enjoyed being under the strong and forceful hands of a man. Which has led me to some internal confusion about my sexuality, as well as countless orgasms.

Let me explain. Up until recently, I have only been with three different lovers and they were all women. Fantastic, caring and nurturing lovers who showed me myself and whom, I will love forever. My last girlfriend, Yamila, was very kinky and liked to experiment with all kinds of dominance and submission styles. We had the best sex I ever had at that point and I was completely fulfilled all night and all day. In fact my awareness of sex increased to almost an addiction. If I wasn’t being fucked by one of her large strap on dildos, I was wearing a vibrating egg all day and having orgasm after orgasm.

One drunken night, Yamila and I were out at a college bar to see a great dance band. Turns out that Yamila had slept with the bass player once in a 3way with her old lesbian lover. She told me that usually she is not attracted to men but since he had long wavy hair and was very feminine, she found him a little attractive. She said it was the only man she had every fucked and that he was magnificent for a guy. I found him intriguing too and pursued Yamila to talk to him after the show.

The bass player, Shawn, was very handsome for a man and you might think he was gay because he was so feminine. He had deep brown eyes and reeked of sensuality. However the thought of cheating on my girlfriend never crossed my mind. I just enjoyed talking to guy.

Yamila and Shawn began doing shots of tequila and then they started talking about the one time that they had a 3some long ago during college. They laughed and joked and I began to get very jealous. Yamila asked me to follow her to the bathroom which always meant a “girls meeting”.

Yamila asked me how I felt about Shawn and I admitted I found him attractive but I had no plans to cheat on her much less have sex with a guy. She gave me a big kiss, slid her hands up my skirt and fingered me in the bathroom until I came on her finger. Then she made me lick it clean. We went back out to the bar to say goodbye to Shawn and went home and fucked like we normally did every night. For several hours until we slept.

About a month later I came home from work early and as I entered our apartment I opened the door to my girlfriend Yamila getting fucked up the ass against the wall and making so much noise that she never heard me come in. I stopped in shock and watched for a minute before I began to cry. Shawn and Yamila stopped fucking and Yamila tried to comfort me. She said it was a one time thing and that she was drunk and was terribly sorry. Shawn left and I cried all night feeling very sad and jealous.

In a few days I decided to forgive Yamila. I loved her very much and tried to understand her point of view. I was very interested in what it was like to be with a man and kept asking her questions about it.

Finally she said, “Listen, how would you feel if the three of us got together for just one night?”

Inside I felt very upset by this because it would mean my girlfriend would be cheating on me. But my curiosity won over and I gave in to the idea.

The next night, Yamila and I went out for a bite to eat and some wine and when we returned to our apartment, we found Shawn waiting for us naked and on the bed. I must admit that I was initially turned on by his naked body because I prefer women. But he did have a beautiful cock even if it was not as large as Yamila’s dildo I was accustomed to.

“Hello ladies.” He said. “I am honored to be here to serve you and your every desire.”

“Oh shut up Shawn and start sucking pussy.” Yamila ordered.

Yamila put a blindfold over my eyes and then someone undressed me and placed me over Shawn’s mouth. He began to suck my pussy and my clit until I was numb and so horny I didn’t care who was doing it.

Then Yamila bent me over and slipped in her favorite dildo up my pussy. Someone placed my mouth over Shawn’s erect cock and he told me to suck. And I did. It was a wonderful warm feeling to have a real cock on my mouth vs. a plastic dildo. I began to have multiple orgasms as I was sucking and being fucked. What more could a girl ask for.

“I am so sorry sweetie.” Yamila told me. “I never meant to hurt you. This is for you in hopes you will forgive me. Do you forgive me?” Yamila asked me as I was getting my brains fucked out.

“Almost” I said.

“Please don’t make me watch your pretty pussy get fucked my a man.” Yamila cried.

“Why not?” I said. “I watched you getting your pretty ass fucked my a man.”

Yamila finally gave in and allowed Shawn to have his way with me. He crawled on top of me and sank his thick cock into my soaked pussy and began to sink it deeper and deeper using motions I have never known before. He was very talented with his hips. He was an excellent lover and better than any women I had been with. I was enjoying it far too much for being a lesbian and began to moan and cry out and smile without even realizing it. Shawn began to kiss my neck very sweetly and then sank his tongue into my mouth.

“No kissing!” Yamila told us. “Anything but that ok?”

“Yes ma’am” Shawn said while he continued to pump my pussy. He fucked me until my juices ran dry after 45 minuets or so. Yamila was watching me and fucking herself with a dildo that she occasionally shoved inside my mouth.

“Yamila, can you get the lubricant out?” I asked.

“No sweetie, time is up. Shawn, it’s time to cum, I can’t stand to watch this anymore.” Yamila said.

Shawn pulled out his hot cock and came all over my small tits as I rubbed it all around just like a slut. And I felt like one too. It was a wonderful sensation to get fucked by a guy under my girlfriends supervision. It was more than worth it to catch them fucking and get this in return. I had a wonderful girlfriend.

Shawn showered off, got dressed, and said goodbye. When Yamila wasn’t looking he kissed me and handed me his phone number secretly and whispered,

“Call me anytime. I am crazy about you.”

I went to bed that night confused. On the one hand I was more in love with Yamila than ever for allowing me the chance to even the score. And on the other hand, all I could do was think about Shawn and his warm cock, long hair, soft brown eyes, and his cum all over my body. I kept these thoughts to myself.

That next weekend I went alone to a bar where Shawn’s band was playing and secretly watched him move on stage. He was beautiful for a man and so darn sexy too. I wished I would not have been blind folded while he was fucking me. And it was at that instant, that I knew I would fuck him again.

After the band finished, I bought 2 shots of tequila and approached Shawn. He immediately gave me a long loving and gentle kiss and held me for a moment. I blushed. The guy really did like me. We did the two shots of tequila and he took my hand and we walked down the street to his apartment saying very little. There was little that needed to be said.

He undressed me tenderly, savoring every inch of my body, licking various crucial soft spots and got me wet and ready in no time. I must have played with cock for 2o minutes. Like a little girl with a new toy. I had never held a real cock before and I was 25 years old. It was wonderful and so well formed. He ball sack was also a fascination for me and I played with them and licked them until Shawn was fully ready to go.

Shawn and I fucked like wild animals for about an hour and I had countless orgasms. I never felt guilty once. How could something that felt so good be so wrong? If anything, I knew why Yamila had succumbed to the forbidden fruit.

Shawn took the lubricant and began to finger my ass. I began to get nervous about it what would be next and started to squirm. He forced himself on me and his weight kept me still. I pleaded with him not to fuck me up the ass but this only excited him more and his showed his huge cock inside of my ass.

It felt surprisingly wonderful and I started to relax. He began to fuck me violently and I began to cum over and over again. He stood me up against the wall and we hand anal sex for more while he reached around and massaged my clit.

I have never known sex could feel so good. I had never thought I would enjoy anal sex. Especially from a man. But as it turns out, I loved it and became addicted to it.

From then on Shawn and I would secretly have anal sex every chance we could. Yamila never found out and I am still her lesbian lover. I seem to be making up now for all those years I never had sex at all.

I suppose I should ask Yamila if she would like to join me and Shawn but I don’t want to chance loosing him.