I had a shirt that helped me hookup with a girl twice. Part 1: Attempted anal on the beach, Part2: successful anal in the woods a few years later [MF]

Keep in mind, i was a virgin at the time of part 1! Although i had had hookups, i only had oral sex and handjobs at this point.

Part 1:
It was the summer before my second year of college and i went to my friends party near the beach. I wore this shirt that had one witty, funny line written on it. I wont specify what it said just for a bit of anonymity, but its not important anyway. I’ll skip all the boring party stuff because nothing relevant to this story happened until right at the end.

It was late, warm, there was a full moon, and we all had plenty of alcohol in our systems. My friend’s brother had some of his friends over at the party. One of these girls, who i will call Alysa, was introduced to me. She was short, barely 5ft tall, blonde, had a fit body, a very cute face, and medium perky boobs. In contrast, im 6ft tall and average build. She was wearing very short cotton shorts and a t-shirt. She thought my shirt was hilarious and shook my hand to meet me, to which i drunkenly commented about how soft her hands were (Tbh looking back, im pretty surprised this ended up working lol).

We were both already drunk and almost immediately took a walk down the dirt road toward the beach, our hands enclosed on each other’s as we walked. We both already knew what we had in mind. It was honestly this quick. We had met maybe 4 or 5 minutes ago and had left to do the deed lol.

“So, do you have any ideas where we could go?” She asked.

To which i replied “I have a few ideas.”

I had already scoped out the place on the off chance something like this would happen lol. There were these little wooden bridges connecting dirt side roads to the beach. They were hardly bridges, more so ladders to get over the sea wall. And since it was 1AM and the parties were basically back at the houses, no one was traveling them.

While walking toward a bridge i had in mind, we stopped walking and spoke a few words. I cannot remember how the very short conversation went, but that is when we first started making out. Under the shade of a large tree on the side of the road, i pulled Alysa’s short tight body close to mine. At that point we were eager to get to the beach so we hurried there.

Once at the beach, we found a spot near the sea wall and under some trees. We immediately got to making out on the beach. Her back was toward the ocean and the bright full moon was off to my right. I quickly got her shirt and bra off revealing her perfectly shaped boobs and she took off my shirt. We got her skimpy shorts off to reveal a small dark blue lace thong. She pulled my shorts down around my ankles, got on her knees, and released my already hard and thick cock and took it in her mouth without hesitation. For a few minutes, i stood there getting blown. Eventually i offered that we lay down, to which we did. She was bent over with her small but toned ass in the air in her blue lace thong and her perfect tits hanging out while she blew me.

Now let me tell you, if you have a penis and you never gotten head on the beach under a full moon, youre missing out because it is amazing!

Alysa was in control. After a while of blowing me, i helped her remove her thong. She spun her body around and moved up to my face. She then began to ride my face with her pussy, moaning loudly in the night air in the light of the full moon. She was riding my tongue more than me eating her pussy and i was OK with that lol. Suddenly without skipping a beat, her weight shifted forward slightly to so that instead of riding my tongue with her pussy, she was riding it with her ass! I had never eaten ass before so this was very new to me. But i was OK with it. She was a very clean girl, no smell or odor. And i remember thinking that it is true what they say, it tastes a little like pennies lol. Her moans continued as she grinded her asshole and pussy against my tongue. In my head all i could think of how much this girl seemed to love sex and it turned me on. At this point in my life, anal was a big fantasy of mine.

I believe what happened next was she got off, and asked if i had a condom. Unfortunately i did not and she said she was not on birth control.

I was blatant with my proposal
“Do you wanna get fucked in the ass?” I asked

To which she agreed.

She got on her hands and knees and bent over, presenting her fit ass to me.

“Ive always wanted to try this” i said
“So have i!” She replied

“Just dont do it the regular way” she said, meaning vaginal.

Now, keep in mind im a virgin at this time and anal sex takes some practice lol. I have a decently thick dick so when i tried to press it into her ass with only the lube from her mouth, it wouldnt even budge inside of her. I began to rub her asshole with my fingers slightly entering it. She began to moan again.

After playing with her asshole a bit, I positioned myself behind her and was able to fit both index finger tips in her ass at once and began to try to stretch her out a little, to which she responded with more and louder moans. I fit both my middle and index finger tips in her ass and her moans increased. As i crammed four finger tips in her asshole, i began pulling apart. I still can hear her in my head to this day

“Oh my god YES YES YES YES!”

Her string of moaning yeses came at i tried to open her up. I positioned the tip of my girthy cock at her back door and pushed. Still nothing! There was no way sex was happening tonight unfortunately. I lay back on my back to where she continued to suck my dick until it was time to leave. On our way back we exchanged numbers and snap chat.

End part 1
Now, obviously that was definitely not the right way to try anal sex lmao. But it was mine and her first time trying anal and we were unprepared. Not to mention that i hadnt even had vaginal sex before. But, we both had a good great time which is what matters.

Stay tuned for next time where we meet a couple years later because she ended up going to my school, where i finally fuck her in the ass in the woods on campus!

Source: reddit.com/r/gonewildstories/comments/11woo9m/i_had_a_shirt_that_helped_me_hookup_with_a_girl