I was 22 years old and in my senior year of college. I was due to get married in six months and had been with my girlfriend (now wife) for two years.

She left to do a semester in France and I was beyond lonely. Most guys would go get banged by a couple of girls, but I was always faithful to my girlfriend.

I decided to get a hotel at the next large city over for a couple of nights to go hiking. I met a guy on a trail, I didn't think he was gay at first and we hiked together and then he had a very small gay-pride flag in the corner of his SUV when we got back to the parking lot off the trail. I asked if the SUV was his and he said it was. Asking him to me, was unnecessary.

Before you laugh, I am not bi, not gay, but did wonder what it would be like...just once. He asked if I was from the area, I said no...I mentioned I was traveling and it turned out he lived right down from the hotel where I was staying. He told me that I hoped I would enjoy my stay and started to get in his SUV...I said, "Hey...uh, I'm kind of here by myself if you are not busy you wouldn't mind getting a drink around 6 with me would you? I have a strict rule not to drink alone and I would really like a beer."

He smiled and said sure...we exchanged numbers and agreed on a place. He left and I sat in my car for what was probably an hour thinking...what in the hell have I just done?

We met and I was so nervous...we had a great talk and after several drinks he said, "I have a pool at my house why don't you come over and we can swim. I have extra trunks". I knew that accepting this invitation was more than swimming, reluctantly I agreed and we left.

After being in the water and having wine for about two hours, we were sitting close and I could tell he was still trying to assess if I was gay or a straight guy that was beyond naive as to what was going to happen. He reached over me for a towel and I looked at him...he ventured closer and I locked in a stare and he kissed me. Almost instantly his hand went into my trunks and he grabbed my hard cock more expertly than my girlfriend ever had.

We made out for awhile he stopped, got out and said, "Let's go upstairs". I hesitated and he said, "It's up to you...". I proceeded.

We soon got naked and he gave me the best cock sucking of my life...He pushed my head down to his cock and he could feel me push back...my secret was suddenly out, he pulled me back by the hair "You've never done this before have you?"

I sighed..".....no....Jeez.. .no. If it freaks you out, I'll go...I probably should have said something on the trail".

He said, "Do you want to keep going or stop? I'm not much for bullshitting around, so yes or no?"

I nodded. He smiled and said, "Then open your mouth like a good little straight boy". I did and felt a cock in my mouth at the same time. I was both disgusted and pleasured by it at the same time. He said, "This is what your girl feels like...remember, no teeth...suck it like you tell her too" He deep throated and gagged me.

He pulled out and said, "Get on the bed, all fours". I complied. He opened the drawer to grab a condom, "I'll go slow...it's going to hurt, not going to lie..pain goes away in a little big but this is a grin and bear it type thing...I'm not much for fanfare, either you have a high pain tolerance or you don't. If I feel this isn't going to work fairly quickly we are done, ok?" I nodded.

He spent the next several minutes getting my ass lubed up and rimmed it...I finally relaxed..he inserted a finger and said, "This is going to hurt like a bitch...but you're gonna like it". He used a lube that had a numbing sensation. Finally he positioned himself behind me...his cock suddenly felt massive..no way was it going to fit!

He slowly, painfully, got the head in...asking me to keep breathing through it. I was sure I couldn't take any more. The pain did go away as he inched more inside. He said, "It hurts less if I can get it all inside". I told him I wasn't sure if I could take it, it was hurting each time he inched it in. He asked me if I wanted him to take it out and I said no. He started bouncing his cock just a little and the second he felt me relaxed, I felt the full shaft enter so deep it felt like it was coming out of my throat. He pulled my hair back hard when I screamed, "How did that first fuck feel? How does having a cock buried in your ass feel? Are you going to be my fag boy tonight? Huh?" Tears were almost in my eyes..."Yes, I'm a fag, it hurts...omg, it hurts". "Just breathe through it" he said.

I was determined I was going to finish this. I faced forward, braced myself and bravely said, "Fuck me..fuck me now". I loudly grunt/screamed every time his full 9" entered my virgin asshole, but I told him to keep fucking me. There are no words to describe this sensation. Every straight guy needs to try it AT LEAST ONCE TIME. "Jesus Christ it hurts...omg, it hurts so bad". I kept screaming.

He speeded up and was pounding me for all it was worth...my tears were real and flowing. "Hurry, please cum...please...it hurts." He squirted more lube which helped some. He pulled my hair back and said "Would you keep pounding your girl's pussy or hold out? Huh? Which would you do? You are going to expect her to spread her legs and service you the way her pussy is supposed to...you wanted to get fucked, you are getting fucked...say thank you, say thank you for fucking your virgin ass".

"Thank you! Thank you for fucking...my virgin ass. Please cum..." His thrusts got so fast and hard I was getting ready to tell him I HAD TO STOP and then I heard his grunts getting loud as I braced myself to take a little more pounding and then He was unloading, pulling my hair back hard each time. After he was done, he flipped me over like a piece of meat and covered my dick with lube and expertly jacked me off in under three minutes.

I slept about two hours and got up, didn't awake him and went back to my hotel in the middle of the night. I was hurting so bad but no regrets over getting my ass fucked by a hot guy.