Losing [F] my anal virginity to my cheating boyfriend’s friend [MF]

I haven’t always made the best decisions especially when it comes to sex. My boyfriend and I had a great relationship for five years. When it was on, it was on. When it was off, it was off. Sex was the power dynamic that made things even in our relationship so when he cheated on me it hurt me a lot. It brought up body and sexual insecurities that I long had, but never faced. His cheating changed a lot for me and this is the story of how I overcame it.

The one rule in our relationship was that my ass off limits. It was never something that appealed to me and away from a few self experimenting sessions with my vibrator it’s not something I was ever curious about.

Ryan was one of my boyfriend’s best friends. He was your perpetual playboy frat brother and always bragged about the girls he would fuck and his workout routine. To his credit though, he was hot and he knew it, but he was also a genuine good person.

I was good friends with his ex Jen, so I knew a lot of the bragging was justified. Jen always said he was slightly below average from a size standpoint, but ate pussy like it was going out of style. For me, if you eat me out with the enthusiasm some people show at the buffet line at a cheap hotel breakfast you’re in.

After the cheating incident, Ryan reached out to comfort me. My boyfriend was a year above Ryan and I, so it felt good to have somebody to talk to about it who knew both of us.

It was a Tuesday night and Ryan invited me over to his apartment to hang out and drink wine. He lived with 4 other guys an off campus apartment that probably should have been condemned, but it had its charm. I walked in and waved hello to his roommates before wading through the empty beer cans to his room. He greeted me with a hug and before I knew it we were both on his bed and he leaned in for a kiss.

I don’t know what I was expecting but I didn’t stop it. I pulled away momentarily as he took my blouse off and unhooked my bra. I kissed him as he gently brushed his fingers across my hard nipples and I moved my hands towards his crotch area. I could feel his semi hard cock against his thighs as we both stepped back and wiggled our pants off.

That’s when his dominate side came out a little bit. He pushed me on the bed and kissed my stomach. Gliding his fingers lower he finally got to panties which were already wet. He could tell I wanted it as I thrust my hips to meet his mouth. He dove in. He kissed my clit as he cupped my ass pulling my my body closer to him. His mouth outlined my slit while he used his other big hand to hold me closer together. That’s when he happened. He flipped me over and shoved his tongue into my ass. I’ve never been eaten that way before and It felt like my blood left my entire body and went directly to my face and my asshole. My panties were drenched and I felt him pull them to the side as I looked back at him.

In that moment, I wanted him to bend me over and spank me. I wanted him to call me his dirty girl, fuck me, claim me, and wrap his arms around my neck and fill my aching ass.

He stated rubbing his thumb on my ass and despite always wanting more foreplay I didn’t want anymore in that moment. I wanted him inside of me. I could feel myself losing control I let out a moan of “more.” He grabbed some lube and I felt the coldness overtake my ass but I knew it was necessary.

I heard the all but too familiar crackle of a condom wrapper opening and I knew it was close. A few seconds later he whispered “now?” and in a moment of reality I laughed and said “I’ve been ready.”

Without much warning he slid into me. I reached back and spread my ass with both hands trying to take him, but I couldn’t. I felt so full as he pushed deeper and breathed harder. I loved every moment and inch of it. I looked back at him and saw his face of determination as he was deflowering ass. Both my elbows were on the bed as I tried to balance myself, but I could feel my pussy throbbing from the unknown pain and pleasure that I was experiencing for the first time.

I yelled back to him and told him to touch my clit. He listened and moaned as he realized how wet I was. In between thrusts, he also spanked my ass. I was close and I let him know.

“Tell me you like fucking my ass” I moaned. He barely acknowledged before I asked again. And again. “Give it to me. I know you can” I moaned again.

He kept thrusting until the moment I said “Matt wishes he could fuck my ass the way you’re fucking my ass.” The thought of fucking his best friend was drenching my pussy and he knew it as he groaned “I’m cumming, I’m cumming.”

As he pulled pulled, I dropped my face into his pillow and my body collapsed in total ecstasy onto the bed. I turned around and laughed as he starred at me and said “thank you.”

“Thank you?” I responded. What do you think I am? He was caught off guard and I told him not to worry.

We both used each other tonight.

Source: reddit.com/r/gonewildstories/comments/ph4rdc/losing_f_my_anal_virginity_to_my_cheating