When I was 18, I was pretty much fully out as a transgender girl attending college in Southern California. I am pretty blessed to be born as a petite Asian male thus making me quite feminine even without the help of HRT. So I was quite excited when some college friends wanted to do a beach trip for our first Spring Break as college students! I had always wanted to try my body in a bikini and although I always believed I had the figure to pull it off, my self-consciousness and fears of judgement always kept me from actually doing it.
So that weekend after we wrapped up finals, I went bikini shopping at a Target with my friend Emily. I picked out a few to try on but the one that stood out was a green and white leaf two piece set that was super cute. Trying on a bikini for the first time and seeing my body exposed, knowing my friends and many people in public would see me, made me so embarrassed! Emily of course seeing me so nervous made me buy that said bikini and off we went.
There are four guys in our group that came to pick us up after Emily and I went to Target:
1. Jason, who was a 2nd year in college, a white mid-west boy who I always imagined as a rich spoiled kid.
2. Hector, a tall lean, Hispanic guy who is a crazy sports fanatic. The guy was such an immature kid back then!
3. Issac, is also a really big jokester who never took school or anything seriously. I do have to admit he was kind of hot though. He had a body like John Cena! Issac probably was at the School gym more than he was in class.
4. Lucas, my roomate’s friend who I had a little fling with early in college
Once we got a spot set up the boys quickly took off their shirts and wanted Emily and I to as well. They were such perverts. College guys are all the same! I was wearing a white sleeveless crop top and some daisy duke denim shorts with my swimsuit under hoping I could stay covered as long as possible. Emily totally betrayed me as she wore the most granny looking one piece you can find. She’s a big girl so I don’t blame her, but she DID go shopping with me so I was upset she made me buy a two piece when she was wearing a one piece!
After pressuring me a bit I finally caved in and reluctantly removed my shirt. My heart was pounding so much even though the initial people to see me were my friends who I had already notified that I was born a male. They kept badgering me to take my shorts off but I totally fought to keep them on.
The beach wasn’t too packed that day as our spring break was slightly earlier than most colleges, but there were still a decent amount of guys around us.
After splashing in the water and playing a little bit of volleyball, Emily and I went back to our camp spot to sunbathe. That’s when I noticed this cute guy a couple feet away from us on his beach chair. His blonde sterling hair was so typical California surfer type. He didn’t seem too tall, but I noticed him glancing at me a few times. When the guys went to go get some food, the blonde cutie finally approached Emily and me.
His name was Todd and he was here with his sister visiting their grandparents and stopping by colleges around town for tours. He was only a senior in high school who was checking out two of the schools that accepted him. Todd was a fresh 18. Like literally 2 weeks into his 18th year on earth, but boy was he cute. He had a boyish charm when he smiled, and I guess I’m such a loser but he was Justin Bieberish to me and you can totally make fun of me for it, but I was a Bielieber when I was younger!
The guys came back and were immediately put off by seeing another guy impede into our group until Todd’s sister came into the picture. Lisa was this gorgeous almost 6 ft model looking beauty. She really was stunning. She was in her mid-twenties and the guys came up with this really dumb compromise.
I’m sure Hector saw Todd and I flirting so he kept teasing poor Todd, calling him a virgin who couldn’t get any girls (I know what he was implying but Todd didn’t get it). Hector was such a jerk even if he was just teasing. But he wanted to keep Lisa around so he proposed we have a little contest.
A lap dance contest -_-;
Hector wanted Lisa and myself to give two guys lapdances, while they judged who was the best. It was such a stupid thing but clearly I had no say like in most matters with our group of friends. Emily was on board too! I think she just wanted to see me squirm and suffer..
Lisa had to dance for Hector and Lucas while I had to give Jason and Todd a lapdance. Surprisingly Lisa was really down for the idea. She was quite the outgoing girl and I bet this wasn’t her first spring break moment.
I on the other hand was so petrified! Not necessarily about the dancing as I actually did cheerleading in high school and middle school so I know how to move my body, but giving a lapdance to a stranger in public was totally out of my league!
Regardless of how I felt, the music started and Lisa jumped onto Hector who was planted in his chair. After a couple seconds of just standing there like a lost puppy, I gathered enough “I don’t give a shit anymore” courage and squatted on top of Jason. Swaying my bare hips on his chest, and bouncing my booty near his crouch actually loosened me up. Jason kept trying to pull off my shorts and I kept slapping his hand off my ass. After that, I wasn’t as uncomfortable though.
Then the second song hit and Todd was there waiting for me. Boy was he cute. I think he was nervous too. As was I. I walked slowly over to him seated in his beach chair, leaned over as seductively as I could and ran my fingers from his lips down his chest to the outline of his swim trunks. Instead of moving at the same quick rhythm as the first song, I slowed down my body to match his breathing. Guys take deeper breathes when they get horny. It didn’t take long for Todd to pop his little guy up. The first second I turned around and lowered my butt onto his lap his cock shot up through his trunks. His hands were so nice and rough (probably because of the sand) gripped around my waist. I was kind of turned on.
I did my best to give him a mixture of sensual belly dancing and slow twerking until Todd asked me in such a cute voice if I would take off my shorts for him. His voice sounded so desperate and yet so sweet. He must have been in bliss. I actually was quite in the zone too! I wasn’t even paying attention to what was going on next to us.
For some reason, I stopped being hesitant about those shorts and my bikini bottom. After all, I tucked my clit really well after years of practice and I’ve worn lingerie in front of guys before so it clicked in my head to finally let go.
Seeing him want me so bad by the look of his eyes turned me on so much. I mounted myself on top of him with our bodies interacting together face to face, crotch to crotch. Then I proceeded to grab his hand and place it on the rim of my shorts where the button was. Together, holding his hand I forced him to pop that button out of the slit. All while I was breathing softly into his ear. From there I slowly leaned my body back and let him pull the zipper of my shorts down (which were quite short already) until my leaf bikini bottom was exposed under. I got up off him and turned around as close as I could to his body and bent over slowly pulling the shorts down.
For the first time in my life, I was on the beach in nothing but a bikini. It was exhilarating. Like shackles had just come off me and I was light as a feather.
Well the song soon ended and I lost the competition obviously because it was rigged from the beginning. (My guys just wanted a lapdance from Lisa).
As Lisa was socializing with the rest of the guys after the “competition” Todd asked me if he could buy me a drink. I said sure and we began walking to a little beach shack at the end of the beach where they served food. During the walk, i don’t know if he was doing it subtly or not but his hand kept brushing against my thigh ever so slightly. He told me I was his first lapdance and that it couldn’t have been better. I was blushing a little as he told me if we had continued the dance a little longer, he probably would have cum. I was totally crushing on him by this point so I took the opportunity while we were walking next to a family restroom and pushed him in there locking the door behind me.
He was confused and it took him a second to realize what was going to happen. I stealthy slid my hand down his trunks (thank god for loose men’s swim trunks) and brushed my fingertips on the skin of his penis. He was much smaller than I had hoped. Probably 5-6 inches at most but I didn’t mind as I just wanted him and he wanted me. He stepped up and kissed me while I fondled his now erect cock and balls. Todd was quite bushy down there, it was not something I had expected looking at his exterior to say the least.
After our lips parted from one another, I got on my knees and began rubbing my hand on his cock through his trunks. I gripped that meat firmly with my hand and began stroking him through his swim trunks which made him moan out loud. I wasn’t sure at first whether he moaned due to the friction of the cloth on his swimming trunks interacting with his penis or if it was because of pleasure. Up and down, up and down I stroked, with each repetition I tightened my grip on his hard cock ever so slightly. Now I knew he was moaning from pleasure because I saw a little spot imprinting on his blue trunks. He had let some pre-cum out.
I took that as a sign to not miss out of the fun and quickly pulled his trunks down to his ankles and proceeded to gently kiss the outskirts of his cut foreskin. Todd was rather silent throughout the whole ordeal aside from the occasional moans. I think he was quite nervous as I noticed him staring at the door knob and lock a few times. Sensing his uneasiness, I wanted to help him ejaculate as quickly as I could and stopped with the foreplay and took his cock into my mouth.
By now my lips were dripping saliva onto the cool concrete floor. I tightened my pouting lips as I slid them through Todd’s cock, first in a condescending rhythm because I felt empowered looking at his face. I had this boy totally under my spell and I wanted him to know that. He wasn’t fucking my mouth, MY mouth was fucking his cock. Then the door knob attempted to move. Someone was trying to open the door. It was followed by a knock. Both our sensual moaning quickly went silent.
Todd was so nervous that he had to clear his throat to gather his voice. I on the other hand silently continued to suck his cock, but now at an even quicker pace. “Someone’s in here!” Todd fumbled out of his mouth. He had a “Oh Shit!” look on his face but his cock was now harder than ever. It was throbbing up against the top of my throat. Todd then lifted his two hands and grabbed my hair pretty aggressively and proceeded to ram my head forward into his cock. It was his pace now. He was clearly on the verge of cumming and wanted to get it over with. My head was in a frenzy by now and my eyes began to close more often. The head of his cock was ramming the tips of my throat after piercing through my lips. My mouth was full of his pubic hair at the end of every thrust. He kept thrusting harder. Harder. Faster. More violently. Harder.
And then it happened. I felt an explosion of force hit the walls inside my mouth. So warm. So thick. So sweet. The sweetest cum I’ve ever tasted in fact. Some cum taste sour, other salty, and occasionally fruity. Todd’s gooey cum smelled and tasted like pure sugar. I loved it. I couldn’t handle it all and neither was I expecting it. His cum was seething out of my mouth and I gagged for a quick second falling back onto my butt and hitting the door with my head. THUMP! Ouch -_-;
I swear I heard a “Is everything okay in there?” on the other side of the door. Or maybe it was Todd as its still fuzzy to recollect that moment after he came to this day. Cum was still dripping out of my burning lips (thanks to his cock piercing my lips so hard), and I was now leaning against the door on my ass with my legs open. My tucked penis was of course no longer tucked and Todd was looking at me like he had seen a ghost. There was an ever so slight bulge from my bikini bottom with the head of my penis poking out. Todd hadn’t noticed that I had an extra something down there this entire time.
After a couple of minutes of recuperation I finally got up. I swallowed some of the remaining cum in my mouth and rinsed off the rest from my face and my bikini top before walking up to Todd. We hadn’t said a word to each other since he saw my bulge a couple minutes prior. He was coming out of the initial shock when he said “You’re a guy?”
“I was born one but I’m haven’t been a male for one day in my life.” I responded. I wanted to cry.
He seemed to understand that. He gave me a nod as if to tell me “We’ll talk about this outside” and opened the door. Outside waiting for us was this burly Mexican Dad wearing cheap looking sunglasses with a couple kids. He seemed like one of those guys who gets drunk on Sundays watching football. As we scampered past him, he gave us the most disgusted look when he saw some white cum stains on the wall of the door which I had totally forgotten to wipe off.
We power walked the hell out of there!
As we made our way back to camp, it was awkward at first but then I began to giggle. This was such an insane, thrilling and crazy spur of the moment situation. I never had that rush of passion before. Todd looked at me and smiled. We stopped in our tracks. Our feet entrenched in sand. His hand now on the back of my head guiding me in. Kiss.
My heart fluttered. This was quite romantic. He told me this was the craziest thing he did and that he didn’t care that I had a penis. When we got back to camp, we found out that the guys had invited Lisa and now Todd to stay at the beach side condo we were renting out for the weekend. Todd looked my way before confirming with his sister.
We went on to have an amazing night which I will write about another time. But thanks for reading! I know this was super in-depth and I didn’t deliver the goods that you all wanted. We did proceed to go further in our exploration of one another that night, and I wanted to have that memory with this, but the post just dragged too long and I decided to separate them into two posts!
Source: reddit.com/r/gonewildstories/comments/4k1dex/my_tmtf_first_time_at_the_beach_wearing_a_bikini