Straight Best Friend Fucked Me

My best friend I’ve known since we were kids, who is very straight, finally fucked me.

My best friend, Justin, and I have been attached at the hip since 6th grade. We’re now in our mid forties. We are still attached at the hip. We still act like 6th graders and my wife of 20 years refers to him as my husband.

For the longest time I kept my bisexuality a secret from him as I wasn’t too sure how he’d react when he found out. Him and I have had some close encounters over the years. One time in particular, we doubled up on this thick Asian girl we met at the bar. Another time, my wife, myself, Justin and this girl he was seeing all took a vacation to Mexico and the four of us were swimming naked in the ocean which ultimately lead to us having sex with our significant others on the beach.

We’ve been friends for 32 years so needless to say, we’re extremely close and we’ve seen each other’s dicks many times. Boys will be boys I guess. When he did finally learn I was bisexual, he completely supported it.

Nothing special about Justin’s appearance. He’s more or less a regular guy. Average height, healthy weight, brown hair. Penis isn’t anything special, 5.5” maybe 6”.

We were all invited to a mutual friends party. They had just bought a big house and were throwing a house warming party that happened to be around Halloween so it was also a costume party. Our circle of friends are all a bit eccentric but not all of them are aware of my sexuality or my love of dressing in women’s clothing.

My wife and I are both overweight and I can actually fit into some of her clothes. We were both excited for this party because we both like playing dress up. My wife went as me, and I went as her. Funny joke, haha, those in attendance that don’t know I’m a bisexual cross dresser thought it was hysterical.

I had a long black wig just like my wife’s hair. I had black bra and matching black satin panties on. Black stockings and heels, (My wife is very goth) and to finish it off a dark purple dress. My wife did a fantastic job on my makeup as well. Much better than I could ever do.

When Justin showed up he enjoyed the whole thing and even complimented my appearance. I knew he would enjoy it, in fact, part of the reason we dressed the way we did was to hopefully cheer Justin up a bit. His most recent girlfriend had broken up with him about 6 months prior and he’s been kind of a bummer ever since. He’s a 44 year old man and never married and no kids. Just kind of bounces around from woman to woman but this most recent one really broke his heart.

The night progressed as normal as it could. We mingled. Played games. Got drunk. Normal stuff people do I think. The main theme, especially from my wife, was giving Justin a hard time about his love life. In fact all the women there were giving him shit about finding a woman to marry and settling down. That’s just not who he is but they don’t understand.

It was the height of the party and everyone was being loud and obnoxious. We were all pretty drunk or buzzed. I had to pee so bad but the main floor bathroom was occupied. So I headed to the upstairs bathroom instead. I sat down to pee, yes I sat down.. I was drunk enough that I feared pissing all over the floor but sober enough to know that I might piss all over the floor. Plus, dressed as a woman it just kind of felt natural. Plus, plus, I had been on my feet all day at work and now been wearing these heels, and it was much quieter upstairs so I just felt like sitting while I peed.

I just stood up and flushed when out of the corner of my eye I saw the door swing open. It was Justin. He quickly closed the door behind him and locked it.

“What’s up?” I asked

Justin said nothing in return. He took two steps towards me, grabbed me by the shoulders and turned me towards the bathroom sink. I placed both hands on the counter as I lost my balance, and before I could ask what was going on again, Justin was behind me. He had his hands on my hips and I could feel his erection pressing against my ass. I looked up in the mirror and I could see the look in on his face, I had never seen that look on him before.

I felt his hands rise from my hips to my chest as he began to massage and grope my breasts. By now my cock was rock hard as well. I couldn’t believe what was happening! I had joked about getting him to fuck me for years but it was always a joke and I certainly didn’t think it would ever happen.

He kissed the back of my neck a few times as he continued to grope my tits. His breathing intensified and I could tell he was getting hotter and hotter. He pulled up my dress and grabbed a hold of my panties and pulled them down. My mind was racing! Was this really happening?! What if someone catches us? My wife is downstairs and she knows I’m bisexual but we have rules. I have to run everything by her and she has to ok everything!

As my brain continued to swirl I heard Justin unhook his belt and begin to pull his pants down. In a frenzy, I grabbed a tube of lotion on the bathroom counter, and in lieu of lubricant, I squirted a small amount in my hand and reached around to find his cock. He was rock hard! I rubbed the lotion on his dick then quickly lifted my knee onto the counter. Justin wiggles his cock around until he found my eager hole and he began to press. He was NOT gentle but in this situation we didn’t have time for gentle. Someone was surly going to come looking for us and we had to get this done ASAP.

Justin thrust his cock inside my ass. I bit my bottom lip to avoid making any noise. I gasped a bit as he began to fuck me. The lotion made him slide in and out relatively easily. His hands held my hips almost angrily as his pumps became more more aggressive. Bent over the bathroom counter staring directly into the mirror I had a fantastic view of him fucking me!

“Jesus Christ, fuck me! Oh god, fuck me!” I whispered

Justin’s breathing intensified. His grip on my hips almost painful. He started letting out small grunt. I knew he was about to cum!

“Cum inside me!” I moaned just a bit louder than a whisper

Justin thrust his cock as deep as he could and arched his back over me like a dog. He was quietly letting out little moans and groans as his dick pumped my ass full of hot semen. I felt his cock pulsing with each spurt of cum. His mouth pressed against my ear I could tell he was barely able to breathe.

“I’ve wanted to do that for so long.” He struggled to say as he slowly pulled his cock from my ass.

I reached down for some toilet paper and began cleaning myself as quickly as possible.

“What the fuck?! Why haven’t you said something?” I whispered back continuing to wipe lotion and cum from my ass.

“I don’t know. Scared I guess.” He answered “..I guess your wife.” He added

“While I found it incredibly hot that you basically came in here and raped me, you just had to ask. I’m sure she’d be fine with it.” I explained as we casually left the bathroom.

As we made our way downstairs, no one seemed to notice we were gone. In reality I was only gone about 4 minutes at the most.

I had to tell my wife what happened and despite her initial shock and even a bit upset, she understood that I lost myself in the moment and wouldn’t have if it were any other person. To this day Justin hasn’t put in the formal request to my wife to have sex with me. When I have brought it up, he changes the subject or just avoids answering questions. I hope one day he comes around and one day because we could have some fun for sure.

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