Popping My Anal Cherry

by Daniel

Gender: Male
Age: 23
Race/ethnicity: Caucasian
Current location: Wisconsin
Highest education received: Some college (not currently in college)
Relationship status: In an Open Relationship
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bi-Sexual, Dominant with females, Submissive with males
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 0

Popping My Anal Cherry

How long ago did this hookup happen? 2 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends turning into Fuck-Buddies

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? His name is Brian. He is 6′ even, brown hair, skinny, muscular, hazel eyes, beautiful tight ass, and a rock hard 7 inch cock. I knew him through my girlfriend at the time (her and I had an open relationship and he was one of her fuck buddies.) I had known him for two years before the hookup. I thought he was a very sexy man.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began one night while at my girlfriend’s house. Brian and I were sitting on the couch, waiting for my girlfriend to return from grocery shopping. We were talking about our personal things when he mentioned that he has been curious about being with a man. I told him that I was bisexual and that I had been with a man before. I had always been on top with my previous male partners and told him it is better than anal with a girl. I continued to tell him that I myself have never been on the receiving end of a penis. As he started asking more questions, I noticed he was becoming erect. He then asked a final question, “Can you show me what it is like?” I responded by climbing on his lap and we began kissing.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Our kisses were getting deeper and faster. He began to grab my ass. This made me kiss him harder, for it turned me on immensely. We took our shirts off and he began licking my nipples. This had never been done to me before, but I loved how his tongue circled around them and how his lips sucked on them. He then started to twist them gently, and I started to breathe harder. He twisted them harder. I moaned in pain and excitement. For some reason, I was enjoying the pain. I kissed him ferociously, our tongues dancing with each other. He said, “Shall we go to the bedroom?” I nodded. He leapt on the bed and I climbed on top of him. The kissing continued and he squeezed my ass harder then before. He began pulling my pants down. I pulled them down all the way, so he could grab my naked bottom. He squeezed it with such force that I moaned in glee. I lowered myself and removed his pants. Brian said, “Danny, this is amazing.” As I revealed his monster 7 inches of erect manhood. I told him, “You want me to put my mouth around your giant here?” He nodded as I began licking his cock. I put my mouth around him and began my blow job. He began moaning erotically, which made me go faster and suck more in. He then said, “Are you my little bitch?” I had never been submissive before, but it turned me on more being called a bitch. “Yes, sir.” I replied. “Let me show you how I treat my little bitches.” he said as he grabbed my head and slammed my mouth on his cock. He started thrusting his enormous cock down my throat. I had lost all control over what was happening, and I loved it. I swallowed his entire 7 inches. He pulled out of my mouth and flipped me over. “Ok, you little whore, my turn.” He began sucking me off. For his first time giving a blow job, he was incredibly good. He was magic with his tongue. After he was done, he said, “Stay right there, my pet.” I replied, “Yes, Master.” as he walked over to the end table. He opened the drawer and got out the anal lube we both use on my girlfriend. He told me, “Lift up your legs, bitch.” I did as high as I could. I could feel him applying the cold lube on my asshole. He made circles around it with his fingers until eventually one went in. I moaned greatly. This was the first time having something in my ass. He fingered me gently. It was painful at first, and then it began to feel amazing. He started going faster and stuck another finger in. This was the best I had felt in bed before. I begged him, “Please, Master Brian, ram my tight ass!” He lubed his cock as I held up my legs. “Here I come whore!” he said as he stuck his penis inside me. It was very painful that first thrust and I moaned hard. Then he continued to thrust and the pain turned into the greatest pleasure I had ever known. I screamed as he kept going deeper and deeper, faster and faster. My ass was being stretched out for the first time and it was magical. I came from the intense pleasure. It landed on my belly and chest. Brian pulled out and started licking up my semen. He then kissed me fiercely. He then demanded that I get on my hands and knees. “Of course, great one!” I replied with glee. I stuck my ass in the air and buried my head in the pillows. He started fingering me with three fingers and slapping my ass. My moans of painful pleasure filled the air. “You fucking little whore!” he said, “You want more of my cock in your ass?” “YES PLEASE MORE!” I yelled. He mounted me and began ramming my ass as fast and deep as he could. I took his entire cock in me. We both were moaning as loud as we could from the pleasure we both shared. He shouted, “Here it comes!” and came inside me. The warm liquid was so soothing, it made me melt. We heard the door open as he pulled out. I could feel his cum leaking out of my ass. It was so good. My girlfriend opened the bedroom door and said, “I never thought I would see the day.” and smiled. She said, “Finish up, and come help. Take your time though.” I flipped over on my back and Brian climbed on top of me and we kissed gently. He said, “That was the best I’ve ever had.”

Did you have an orgasm? Did your partner(s)? Yes and so did he.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t, for we both knew we were clean.

What were your REASONS for having this hookup? The mood was right and to help my friend find out he was bi.

Were alcohol or drugs involved? If so, how much? No.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We both cleaned up and helped my girlfriend with the groceries. All three of us then watched a movie, snuggled with each other, and feel asleep. I felt amazing about this hook up. My expectations were that we can do it again, and those expectations were reached. Brian and I are fuck buddies now, and we’re both enjoying ourselves.

To whom did you talk about the hookup? How did they react? I talked to my girlfriend about with Brian. She reacted with jealousy, as the story turned her on and she said that next time she wants to watch.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both of us.

Do you regret this hookup? If so, why? No, not at all.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best things were helping my friend  find out that he is bi and losing my anal virginity. The worst thing was that we became too tired to go a second time. That hook up taught me that I love being submissive with a man more than being in control.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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