My buddies want to take me out for my 30th birthday. I normally don’t go out, I’m much more of a homebody than other people in my social circle. They say they’ll buy me drinks all night, and have been begging to take me out for the past couple weeks. ”C’mon man, it’s your 30th birthday! You never go out with us. Let’s get fucked up!” they said. I couldn’t say no, although my plan was to let them all get shitfaced and slip out early.
We live in a small college city, so the bars are usually filled with a younger crowd. Maybe I’ll get lucky tonight and go home with a pretty college girl. That would certainly top my birthday off in a delightful way. I’m not the most suave guy, but I’m no Quasimodo. We get to the first bar of the evening around 9. The scene is good. Not too crowded, but plenty of people enjoying their night. We all take shots to start off, then another, and another. My buddy’s choice of tequila will sure make for an interesting night. The bar a few blocks down has a good birthday wing deal, so we stumble out of the first bar and make our way down the street.
The second bar was packed. I didn’t think we’d get in but all my buddies convinced the bouncer to let us in. This bar was awesome; good music, good food, good drinks and beautiful ladies. We finally made it up to the bar and ordered our drinks and my wings, barbecue of course. This time around we all got beer. Mixing alcohol can end your night quickly, so I made sure to get a glass of water too, no ice. An hour goes by and the wings are long gone, the beer keeps coming and one of the guys is up at the mic singing the same damn song as always, Livin on a Prayer. What a goof. The night moves on, and I actually got a number from a beautiful girl going to the pharmacy school. She told me to text her later. If I don’t forget or pass out early, maybe I’ll get that birthday ending I wanted. We decide to go to one more bar downtown. The night started with 7 of us, but it was down to 5. The other two didn’t handle that tequila and beer mix too well. We hop in an Uber and we’re off.
We pull up to the bar, hop out of the Uber and hang outside while my buddies smoke. There was this woman outside, puffing on a juul with her friend. They were both really pretty. I walked up to her and asked if I could take a few hits, “I only do this when I’m drinking.” even though that was not true. I just wanted an excuse to talk to her. She was short, maybe 5’5, smooth skin, perfect lips, petite. Her proportions were just right. She looked like the type of girl you could throw around in bed. The fellas were heading in so I I said goodbye to her. She said she’d see me inside, nice. More shots, this time it was pickleback shots. If you’ve never heard of it, it’s a shot of whiskey followed by a shot of pickle juice. It actually wasn’t all that bad. More beer and more shots. How am I even functioning? Probably all that water I keep drinking between beers. I’m sure the wings helped. We’re hanging out at a booth, reminiscing of our younger days. We’ve all been friends since high school. I feel lucky to have these guys in my life. We’re all looking a bit out of it by now. My lady friend from outside finally found me. She asked if she could sit with us, said her friend called it a night. She introduced herself as Sarah. What a babe. My buddies got the hint, and they all slowly started heading out. After a bit it was just Sarah and I talking. She was in her junior year and was studying to be an Environmental Attorney. She wasn’t from the area but she planned on staying after she graduated. I told her about my job working for the state, and my degree in who would have guessed, environmental science, and my 20 year old cat Francis. By now it was about 2 am and we were both having a great time talking. She asked if I lived close by. She wanted to meet my Francis. Of course I knew where she was going with this, so I ordered us an Uber and the night continued…
We got to my place, an old brownstone converted into apartments. I love my home. I stumble with my keys, Sarah helped. She wasn’t as drunk as I was. I barely have any idea what’s even going on, but I managed to keep it together. Am I really about to have a one night stand? I’ve never done this, but Sarah was feeling me and I was definitely interested in her. I grab us some water and some popcorn while she’s hanging out with Francis. She said she’s never seen a cat this old. He’s still a kitten at heart. I’m convinced he’s immortal. We pop on a movie, and talk through the whole thing, cuddled up on the couch under a blanket. For August it was cold. I wouldn’t want it to be any other way at that moment. She’s getting handsy, rubbing my thigh and nudging my shoulder with her cute little nose. I grab her thigh and go in for a kiss, she kisses back. After some time, she says she wants me to make love to her. Wow, this is happening. I feel like a kid about to go to Disney World. She grabs my hand and brings me into my bedroom.
Sarah playfully pushes me onto my bed and tells me to take my pants off. This is happening so fast, I’m nervous but I feel like I’ve never been this turned on in my life. She climbs on top of me kissing my neck, rubbing my leg and slowly pulls my boxer briefs off. Her tongue against my inner thigh was sending me to almost orgasm alone. Finally, she works her way to my rock hard dick. I was so hard. The way this woman sucked my dick was incredible. I told her I was going to cum and she stopped. She didn’t want to end the night there. She came up and started kissing me more. I took her top off and started to kiss her perky little breasts. After a few minutes she stopped, got up and sat next to me. “I have a confession” she said. Oh boy, she has a boyfriend. I can’t help this girl cheat. It wasn’t that though, it was something else. “I am not who you think I am.” What could she be talking about? Did she lie about school? Her age?”… I am a trans woman.” Woah… wait, what? I knew what she meant but I still said, “What do you mean?” She started telling me that she has been in HRT for some years and that she’s always been a woman. Well this was awkward. I won’t lie though, I’ve jacked off to trans porn many times. It was always kind of a fetish, but I never thought I’d actually be in a situation like this. I told her I needed a second to think all this through. She seemed upset and started to put her shirt back on. Her tits were so perfect. The HRT did the job. I told her to stop. I pulled her back onto my bed and told her I wanted her. She seemed like she was expecting me to kick her out, but what she didn’t know was that I was even more turned in now. She said she was sorry for deceiving me, but I told her to hush as I pulled on her tight jeans.
I couldn’t believe this, I’m really about to do this. Her pants slid off her hips and out popped her hard dick. I’m not sure how I didn’t notice this at first, but to be honest I wasn’t really looking for a dick in a beautiful woman’s pants. She closed her eyes and started rubbing her tits together as I gazed at her dick. It was bigger than mine, not by much, but it looked so big up close. I grabbed it by the base and went in for my very first blowjob. I can’t say I was doing great, but her moans said otherwise. After a while, my jaw started to get sore and she noticed that I was slowing down. She flipped me over and went back in for seconds. Wow this really is the best blowjob I’ve ever had. I told her I was going to cum, and she stopped again. She then straddled my chest and propped a pillow under my head and began to fuck my face, hard. I grabbed her ass and pulled her in closer. She was riding my face so good. Looking up at this beautiful woman while her hard cock is in my mouth was something out of one of the pornos I watched. She pulled back from me and got on all fours and said, “will you fuck me now?” I quickly rolled on a condom, and slapped her ass. She loved that. My heart was pounding. I looked down at her little asshole and slowly started to put my dick in. I was so nervous I was going to hurt her but she begged for the whole thing. She started backing up into me, pushing my whole dick in her. Her asshole was grabbing me so tight, and it was amazing. She then got onto her back and put a pillow under her waist. She said that’s how I can hit the spot. I’m fucking her, staring into her eyes and holding onto her dick, stroking it as. Her eyes were rolling into the back of her head. She kept saying my name. I was about to cum but she exclaimed, No!”. She pushed me off and quietly asked if I would be in to receiving. This was a little more awkward for me. I mean, I’ve played with my ass before, and I even bought a little dildo to play with, but her dick was much bigger than the dildo I’ve used. She promised she would be gentle.
I’m laying on my back as I watch her put her condom on. She starts kissing my neck down to my chest to my thighs. Then, she spreads my legs and puts them up in the air and tells me to hold put my hands behind my knees and bring my legs to my chest. Slowly she starts licking my balls and pulls my dick toward her. She took my condom off and starts to lick my shaft. I felt so vulnerable. Her tongue starts to move to my asshole and she began kissing it. At one point it felt like her whole tongue was inside me. My cock was pulsing out of control. I told her I wanted her in me. She spit on my asshole and rubbed the rest of her spit on her dick. She stared really slow. Just the head. “Are you okay?” She asked. I nodded and smiled. Deeper she went. The feeling was unlike anything I have ever experienced. It felt different, but I didn’t want it to stop. I asked for her to go harder, and she began pounding me. My legs were shaking. I had to take a minute so she pulled out and kept sucking my dick. I quickly realized how bad I wanted her back in me so I told her to lay on her back as I straddled her and put her dick in me. I started on my feet, slowly squat riding her all the way up and down. Eventually I went to my knees and she began thrusting upward. Stroking my dick as she looked at me in the eyes while I was riding her. She said I was doing better than she thought I would. I bent down and we started to kiss passionately. She asked if she could come yet and I asked her to take her condom off so I could finish her off. I got off of her and took her condom off. She laid me down and started to get into 69 position. Fucking my face as she sucked my cock. I grabbed her ass and told her I was coming. I couldn’t hold it anymore. She went quicker and grabbed my balls as I came in her mouth. I saw black for a moment. My balls ached. After I caught my breath I told her to stand up on the bed as I got on my knees and started to suck her balls and stroke her cock. She grabbed the back of my head and said she was going to come. I grabbed her ass and pulled her whole cock into my throat. I felt her cock pulse as she came down my throat. I looked into her eyes while she came. She bit her lip and I felt goosebumps on her ass. I pulled her down to me and we kissed more. Exhausted, we laid down and got under the covers. By then it had to be almost 5 am. I asked her to stay and she happily said okay.
We stayed awake the whole time. I was holding her in my arms and Francis was laying on my legs. You could hear the birds singing. It was morning. We barely talked since making love, just kissing and cuddles. When the sun was up I told her I had the day off and asked if she wanted to go get breakfast. She said she had schoolwork but it wasn’t that important. We took a shower together. Watching the soap slide down her breasts and drip off her cock was so hot. We got out, dried off and then made love again. Afterwards, we met up with my buddies from last night at breakfast. I could tell they were pretty hungover but I was lucky enough not to be. That water helped a lot. They all grinned when I walked in with Sarah, what they didn’t know was that I had the most romantic, sexual experience of my life.
She thought our night together would have been a one time thing, but it wasn’t. That was the best birthday ever. Since that night, we’ve spent almost every day together. We hike, canoe, camp and make love multiple times a day. I think I love her.
Source: reddit.com/r/eroticliterature/comments/dpmpq1/birthday_boy