The year I graduated from college, I did an internship in Miami. I enjoyed my time in Miami, especially meeting Latina girls. I would often go to the same bar where there was a friendly Latina bartender who also lived in the same apartment complex as me. Every time I saw her at the bar or around the apartment, she would flirt with me. Although she also flirted with many muscular black men, I was the only non-colored guy she showed interest in.

One night, I went to a bar/club in South Beach and saw the attractive Latina bartender. She was 5'10" tall, weighed 175 pounds, and had a great figure with curves in all the right places. She was wearing a bodycon tight pink dress. I was attracted to her, but I knew she would probably not be interested in me and was only flirting for tips.

I talked to her a few times at the bar and eventually asked her to dance. To my surprise, she said yes. While we were dancing, she pressed her butt against me. This was always a risk for me with attractive women because I had a small penis. I was a great dancer, but if I got an erection, they would feel how small I was. Despite this, we continued dancing in this manner for a while, and then she grabbed my penis on the outside of my pants and whispered in my ear, "I prefer guys with small penises because they are the best for anal sex." I laughed and asked if I was small.

She replied, "Yes, but don't worry, baby. I'll make you orgasm harder than ever before." I agreed, and she turned me around, spanked my butt, and rubbed against me. We danced for over an hour. At midnight, she said she was leaving and might see me another time or at the bar later that week. I was surprised and asked why we weren't going home together tonight.

She giggled and said, "Not tonight." When I asked for an explanation, she said, "Babe, you can't know the truth. You're very attractive, but I don't want to risk getting hurt again." I asked how she had been hurt, and she mentioned being physically assaulted. I reassured her that I would never do that and suggested that if she didn't want to be with me because of my small penis, I could pleasure her orally.

She smiled and said, "That's the thing, I don't have a vagina. I have a large penis." I was shocked and didn't believe her. She grabbed my hand, placed it under her dress, and guided it to her tucked penis and testicles. She told me it was tucked, but could I feel it? In disbelief, I nodded.

Then she revealed that the last time she brought a random guy home, he beat her up upon discovering her secret. That's why she preferred to sleep with regulars from the bar. I asked if she only received anal sex, and she explained that it depended on the situation, using the terms "topping" and "bottoming." She winked at me and said she would be the one "topping" me. I laughed and mentioned that I had been anally penetrated before, so she shouldn't tempt me.

She expressed doubt and said she didn't believe me. To prove my point, I guided her hand to my small penis. She suggested going to the bathroom since there were single stalls available. We entered the bathroom, and she offered to either have anal sex with me there or receive oral sex. I laughed and said it wouldn't be possible in the bathroom, so we should go to my house. Curious, she asked why, and I explained that wearing panties to the club was a way for me to avoid casual hookups. She laughed and insisted that I show her my panties.

I pulled down my pants, revealing my purple lace cheeky panties. She giggled and complimented me on how sexy they looked. Then she raised her dress, revealing her untucked penis from her black lace panties. It was large, uncut, and approximately 8-9 inches long with significant girth. I asked how she managed to tuck it, and she smiled, saying that sometimes she inserted it into her own anus. She then instructed me to suck it before she would proceed to penetrate my anus. I got on my knees and began performing oral sex on her penis. Afterward, I stood up, and she pulled aside my panties and spat on my anus. As she inserted her penis, I moaned in pleasure. She assured me that only 25% of it was inside and encouraged me to relax. She then pushed further, and despite my initial resistance, she managed to penetrate me completely. I screamed, and she giggled as she thrust in and out.

Curious about the duration, I asked her how long she intended to continue. She replied that she would keep going until she ejaculated inside my anus because it was the only way to tuck her penis back in. I moaned and pushed my hips back to meet her thrusts, now finding pleasure in the experience. She asked where she should ejaculate, and I requested that she do so inside me. She agreed and filled my anus while I moaned and my panties became soaked.

Afterward, she withdrew her penis and asked if I wanted to dance more or go home. I asked if she would be coming with me either way, and she confirmed that she would. I suggested we dance some more, and then we went to her place.

Once there I asked if i got to fuck her ass. She laughed and said no you are a bottom with that little cock. I said it’s not that small I have fucked lots of girls. She giggled and said oh, how many? I asked since when? She said since ever.

I told her well I had a longtime HS and longtime college GF so that’s 2. Other than that 3 before Miami and 2 in the 6 months since I have been here. She laughed and said 7 total? I respond yeah but two I dated for 7 years.

Then she said how many fucked you more than once? I said girls? She said oh so you have fucked guys? Drunk and not thinking I said no I was always the bottom for guys. She laughed and said oh my let’s start with girls how many did you fuck more than once and how often?

I said my 2 GFs. The HS one we fucked like 10 times and the college one fucked my ass all the time? She said fucked your ass? Was she trans? I said oops not what I mean no she used a strapon.

She asked so when did you last fuck her? I said um after she started pegging me we slowly stopped fucking and I would lick her or get pegged. She say that’s hot, lucky girl did you ever come from the strapon? I said no.

Then she said so guys too? I said yeah 8 so there 15 total. She giggled and said so more guys have fucked your ass then girls you have fucked. I said well I mean they were my roommates.

Then she asked if I ever came from just anal. I said yes a few times when in chastity and panties but when I get hard I always stroke. She said omg who locked your cock? I said my ex gf. She giggled and said do you are submissive, Why don’t we make a deal. I said ok what?

She said you wear these and pulled her panties off handing them to me. Then she said and I get to fuck you til I cum three times. If you cum hands free. I get to fuck you 20 times. I said ok and if I don’t? She said you can fuck me 20 times, However anytime you cum handsfree from me fucking you after you cum handsfree the first time we add 10 fucks. I said not gonna happen I don’t cum hands feee like ever.

She said challenge accepted. I slid on her panties, and she penetrated me anally. First she fucked me with my legs wrapped around her kissing me as she fucked my ass. Her stomach had my cock pinned and I came as my legs shook. I told her not fair her tummy rubbed it.

She said ok climb on top. Then I rode her as she wiggled her hips and squeezed my ass. She pulled me down in a kiss as she came in me I came again.

I was panting hard when she pushed me off and started fucking me doggie spanking me telling me what a slut I was as she and I came together again.

I moaned I came three times. She giggled you get my cock 40 times. I moaned yeah. Then she said do you wanna be a top or be my bottom boyfriend? I said your bottom boyfriend. She said good you will also be cleaning cum from my booty if my top bfs come over ok. I moaned yes as we both fell asleep.