A Femboy's '21st Birthday in Vegas

One of the things me and Dan, my boyfriend during college, had a little difficulty with, was the timing of having sex. As a college student with classes starting at 10:00 a.m., if I had free time, it was often late into twilight hour and Dan, who was much older and worked for a window installation company, was more available in the afternoons on weekdays. Sure, I would go see him after class whenever I could, but as a strict bottom femboi, I didn't have enough time to get dolled up and ready for romance. It was a routine that involved bathing, shaving my legs, exfoliating my body, shaving, or plucking with tweezers, the hairs around my privates, cleaning myself inside and out, and applying my favorite watermelon lube and glitter lotion before finally changing into a cute pair of panties and a girly shirt or tank top. On special occasions, I'd even put on some very light lipgloss and fake lashes to appeal to my Danny. Other fems can surely relate, that preparing for a date can be a pretty lengthy and tedious process.

Because of that, there were many days when I would visit Dan after school for dinner, and I would have to stop his advances for sex because I didn't have ample time to fully prepare and I didn't want him to see me naked any less than my best. That usually just meant that I could please him with my mouth and it became a weekly thing where I would swallow him during my afternoon lunch break if he wasn't at work and go back to class in the evening. We still had anal sex but it was much less frequent than you might imagine and it became this thing that we'd plan in advance for. For example, if we took a weekend trip somewhere and stayed in a hotel, we both knew we'd be having sex so I would go get my body hairs waxed at a salon (only my legs and underarms). The positive side of not doing it as much as we both would've liked, was the fact that sex still felt very special and I enjoyed feeling Dan inside of me as much as I did when I lost my virginity to him a few years prior.

One year, with summer vacation right around the corner Dan suggested we spend my 21st birthday in Las Vegas. It would be my first time in Vegas and I wanted nothing more than to unwind from finals and celebrate my birthday with my handsome boyfriend. Dan was 55 and more than twice my age but I never felt more comfortable with a man than with him. We met online via craigslist and I was very attracted to his mature personality. All throughout high school and college I never found guys my age to be attractive because of how immature and arrogant they all were. Dan was my first boyfriend and he treated me like his girl and I could be my feminine self around him; something I've had to conceal all my life. We did get weird looks from time to time in public and we hardly showed any PDA because of it, but in private, it was really a normal, romantic relationship.

Dan told me he'd book everything for us and would even pack for me. All I needed to do was show up with toiletries and my ID. The surprise element was so very exciting and I couldn't think of a better way to spend my 21st birthday than with the man of my dreams in Las Vegas. It couldn't come fast enough. In the meantime, I decided to get my entire body waxed, except for my pubes. It's not that I didn't want to get my pubic area waxed but I always felt shy about that. I scheduled the appointment three days before departure so that I could be silky smooth for my man. The underarms area always hurt more than the legs and thighs but it was a small sacrifice to feel sexy and confident for my man. As for my special parts, I left a little landing strip about the width of a #2 pencil above my dick and completely removed the rest with tweezers. My anus, which Danny called my "pussy" didn't have much hair to begin with, but I made sure to shave the few loose hairs around the area. Dan had a thing for my pussy and early in our relationship he would beg me to send him close up photos of my butthole for his eyes only. I never understood why anyone would find my butt attractive but I felt naughty and sexy doing it for him and if he enjoyed it, that's all that mattered to me. Ever since then, I always kept myself groomed down there. I wanted to look my best for Dan even under my panties and he always appreciated it.

Few weeks passed and we left for Las Vegas on my actual birthday, a Friday. We would be returning on Monday and that's about all I was told. On the date of our departure, I got a text from Dan telling me to wear a cute thong for him so I picked out my red thong and wore it underneath my low cut boy jeans along with an inconspicuous unisex t-shirt. The rest of my clothing for the week was picked out by Dan as he insisted on surprising me with all new outfits for this trip. The thought of it all was so exciting for me. I was also excited to use my ID to get into bars legally for the first time and was looking forward to that.

Dan picked me up in the afternoon and we drove to the airport. He had two small suitcases and carried them both for me, which made me feel like "his girl". Upon arriving at the TSA, I suddenly felt nervous that the agent patting me down would somehow detect my thong and thigh high stockings that I was wearing underneath my jeans but I got through without any unusual attention and we boarded our short flight to Las Vegas.

In the plane I leaned my head onto Danny's shoulders and we held hands. Just thinking about how much sex we would be having made my heart beat extremely fast and I had a small erection in my panties for most of the flight. I felt his manly hands tighten the grip around my fingers as if he knew what I was thinking.

After landing, we checked into a suite at the Paris and I was blown away by the luxurious room and the view of the strip. We also had a big jacuzzi tub and a little living area. As I was admiring the evening view from the panorama window, Dan kissed my neck and wrapped his arm around my waist. He hastily moved to take off my t-shirt and surprised me by even unbuttoning my jeans. He removed my clothes rather aggressively like someone who had been thinking about fucking all day long. We weren't in the room for 10 minutes and I was standing in front of him wearing nothing but my red thong, striped knee-high stockings and heart sharped pasties that I recently bought on the internet (Amazon wasn't as popular an option back then) on my nipples. The room temperature was perfect and I have to admit, I felt pretty sexy in my skimpy little outfit, if you could call it that. I was ready to have sex right then and there, but Dan surprised me by handing me a small bag with a bow on it.

"Happy birthday cutie pie. I love you." He wrapped his arms around me and presented me the pink bag. Inside was a small box.

"Awww. I love you too Danny. You didn't have to. What is it?" I slowly opened the box and inside was a cute little buttplug with a heart shaped crystal on the end as a decoration along with a bracelet with red and white gemstones on it. Realizing what it was, I blushed a bit.

"I thought I would start off by giving you a small gift Jamie. Do you like it?" my Danny asked me.

It was my first buttplug and I'd always wanted one, but being so shy about sex toys, I reached for the bracelet first.

"It's so beautiful baby. I love it", I reveled. I tilted my head back as Dan's arms remained tightly wrapped around my tummy and gave him a light kiss. He helped my put on the bracelet on my left wrist.

"You can wear this bracelet whenever you have the other gift inside of you. That way I'll know whenever you're ready for sex." Dan's hands were now massaging my breasts. I was pleased to see my red heart stickies staying on my nipples the entire time he squeezed my soft little tits. He leaned in for another kiss and I opened my mouth and invited his tongue. I was pretty turned on by then and I took Dan's clothes off too with some assistance and cooperation. He was rock hard and beautiful as always. His cute pot belly was peppered with gray and black hairs that led all the way to his large pornstar-like cock. He once told me he took Cialis or whatever for making him hard, but I'd like to think that I was the reason for his erection and not some pill. Either way, seeing how turned on he was made me even hornier.

I looked at my boyfriend in the eyes and took a literal breather from making out. He was still standing behind me and we were both facing the glimmering Vegas strip. I could see Danny's naked body in the reflection of the window. The sight of my naked boyfriend always turned me on. He was a well built, wide, 260lbs with dark body hairs all over with large thighs and a seven inch erection to match. I was 5 inches shorter than him and about half his weight, no body hairs and a 4 inch erection at its largest. I always marveled at the contrast even thought we were both gay men. I reached back and grabbed for his cock. It was too irresistible. His hands massaged my recently waxed thighs.

"Can you help me try the birthday gift?" my voice was getting higher and more flirty which I knew Dan could recognize as a sign me getting hornier.

"Of course cutie pie. Is your vagina smooth for me?"

I slipped my thong to the side and spread my feet just enough so that Dan's fingers could reach down there. I held his hand and guided his fingers right to my warm hole. It turned me on that he called it my vagina and it just felt so appropriate for a femboi like me. I felt his slightly cold hands put a gentle pressure on my pussy and rub me in a circular motion.

"I shaved it just for you baby", I whispered to him as he kissed me with full tongue and prevented me from saying anything else. I moaned with his tongue in my mouth which seemed to turn him on even more as his kisses got more and more passionate and sexual.

Dan reached over to the table and grabbed my new buttplug as well as some lube that was also in the gift bag. He also grabbed the bracelet and put it on my wrist. "Don't forget to put this on ok?" Dan reminded me.

I turned around to face my man and our tongues swirled around each other's mouths again. I could kiss him all night. I closed my eyes and let myself enjoy the moment. I felt the cold metallic buttplug press on my anus and I relaxed my muscles to allow Dan to push it in. I wrapped my arms around Dan and held onto his shoulders tightly with my face pressed against his hairy chest. He pressed a little harder and I let out a little moan. I reminded myself to relax. Dan started to push the buttplug in just a tiny bit, in and out. In, out, in a slow and steady rhythm, each time pushing in just a little bit more until my boy-pussy swallowed the buttplug and suctioned it into my body. I remember it being a little more painful than I'd imagined but once it was inside, the discomfort turned onto a sensual, erotic feeling that made me a little weak. Dan readjusted my thong and slipped it back to where it belonged, covering the buttplug with the thin strip of cotton between my butt cheeks.

"There. How does that feel, cutie pie?" Dan asked.

"Danny, I love it. I feel like I have a piece of you inside of me. It's making me really horny."

"Happy Birthday baby." Dan kissed me on the forehead. "It's making me really horny too, see?" He put my hand on his erect penis to show me how turned on he was. He removed my panties and once again wrapped his hands around my tummy from behind. I was now naked other than my knee high stockings and heart-shaped pasties. He began to play with my cock and the sensation of having a buttplug inside and being stroked from behind by my lover was overwhelming. I started moaning and breathing heavily and my mind went blank. I felt weak to the point of not being able to remain standing but Dan was a strong man and he held me upright with his other arm. We remained standing as he played with my cock from behind.

"Danny..." I attempted to speak to him in between moans.

"Yes cutie pie?" he slowed down the pace of his strokes.

"Can you do that thing for me where you put your penis inside of me and make me feel good?"

"Inside where baby girl?" Danny wanted me to say it.

"My pussy" I said with a hint of embarrassment. It still felt weird calling it that myself. "Please? I want to feel you inside of me for my birthday."

"OK cutie pie. I love you" Dan said. Always the sweetheart.

"I love you too." I made a quick bathroom stop to rub Vaseline coconut oil on my body and gave myself a few sprays of my favorite Juicy Couture perfume. I found Dan already laying on the bed stroking his cock so I joined him and gave him a blowjob. Having a buttplug inside and sucking cock turned me on like never before. I looked up and saw him staring down at me so I took his 7 inches as deep as I could down my throat and started bobbing up and down on his dick. He told me to slow down because he was about to cum and a part of me wanted him to shoot his load in my mouth. I would've swallowed him like I always do but that night we both wanted more.

He pulled my head off of his cock and asked me to get on my hands and knees. I spread my legs apart and turned my butt toward him and got on all fours. He kissed my pussy with the buttplug still inside and I could feel his tongue rotating in circles around my hole. He pulled the buttplug out, which took a little effort since it was lodged in there pretty tight. He moved closer and I felt his penis come in contact with my butt.

"This is my favorite part right here Danny", I said from the doggy style position.

For the entire two years that I dated Dan, he always was gentle and respectful about my needs when it came to anal sex. He knew he was larger than the average man (although I'd never had sex with anybody else until then) and he always made sure to not cause me to feel any pain or discomfort.

He gently pushed the tip of his cock inside of me and paused to let my pussy relax and stretch open. His dick went in much easier than usual, probably thanks to the buttplug that I was wearing until seconds ago. My eyes began to tear up as they frequently did during sex and I buried my face in my pillow to wipe them off. It kind of became a habit to moan into a pillow because Dan lived in an apartment that wasn't very soundproof. That night in Las Vegas, however, I knew I could be as loud as I wanted and I let out a few audible moans.

One of the weirdest things that happens to me, even today, is that my penis gets really small during those first moments of penetration. It gets larger later but during the first few minutes of bottoming, my penis shrinks to about an inch. Early on, I preferred to have sex in the dark because I was so conscious and embarrassed about my dick size but by my 21st birthday I was totally ok with the lights being on and I actually wanted him to see everything. I wanted him to see our bodies connected and sharing an intimacy that nobody else in the world can say they've experienced with me.

On that night I was in the doggy style position the entire time. I don't know how I remember these things yet I can't remember my best friend's wife's name, but it was one of the most memorable fucks I've had in my life. Let's just say Danny fucked my brains out. I remember thinking how much I wanted to be with him for the rest of my life and how certain I was that I was gay. There was always a hint of doubt that maybe being attracted to guys was a "phase", but as Danny was pumping his love in and out of me, any cloud of uncertainty dissipated away. I ended up squirting all over the pillow and the bed and almost immediately after, Dan ejaculated deep inside my body. The pillow that my face was on had huge wet spots from the tears that kept running down my face as well as my semen that shot out of my 4 inch erection. Evidence of an explosive, steamy sex session.

We both hugged each other in silence after that and he picked me up and carried me to the jacuzzi. We took a bath together and he told me about a LGBTQ pool party we could go to. We talked about how Las Vegas was very non-judgmental and we could even hold hands in public at certain casinos. He even bought me a bikini, he told me and we made out in the tub. He also revealed that he had another gift for me as a surprise tomorrow. Oh, and he made me cum one more time in his mouth too but we did that kind of stuff all the time. Being in a bikini in front of others would be a whole different story. I decided I would wear my new buttplug to the party tomorrow and Dan would know because I would have my bracelet on.