Tag: Straight

This took place approx 2 months ago. I had a short-lived FWB situation w/ a girl who was briefly single before getting back together with her BF a couple of weeks later. However, during that time, we definitely enjoyed trying things she never got to experience previously. This of course, includes an awkward threesome with another girl.

My FWB (Sara) was recently single and looking for something casual when we first started talking one day online. She was cute, white, curvy but not overweight, short with light brown hair. By the next day, we had met up for dinner and ultimately ended the night back at her apartment. We only had sex twice that night, but as we relaxed during sessions, we asked about each other’s kinks. I admitted to liking threesomes, and she confessed to wanting to try both MFM & MFF, being more interested in the latter. I asked if she actually wanted to try, and as we talked about it more and more, she became increasingly excited and agreed to try. Sparing details, we ultimately found a willing candidate via Tinder. She was a super cute, white hipster girl with a couple of tattoos and long, straight black hair. The only catch was, this girl (Anna) was not really into girls but wanted the experience. Sara was secretly bi, but we ultimately agreed to just some light touching between girls. Read more »

Some years ago I served in the US Navy. I was stationed in San Diego, Ca. I was young and never really been in a big city before. I’m from a small midwestern town surrounded by farms and coal mines. I was single and I just wanted to get laid. At the time I wasn’t 21 yet, so the bar/club scene wasn’t a good way to meet girls. So naturally, I turned to online dating apps… I was instantly hooked. As well as sites like craigslist and backpage. I was seeing a different girl every weekend or extended leave period. Didn’t always end in sex but I felt like a real player. Didn’t matter to me if I paid for it or not. I met this girl, we’ll call her… Marjorie. Her profile pix were great. She had a great body, curves in all the right places, she was latina, her hair was dyed pink, and she had her tongue pierced. Man, I was intrigued. Of course, did I read her entire profile… Nope! I simply did what I always do. I skimmed through looking at the high lights. Yeah, you’d think a high light would be “btw I’m a tranny”. Yeah, it was there but all I saw was ” tranny” and being the young midwestern uncultured man that I was I assumed tranny was short for transmission, like from a car. Her dad owned and operated a mechanic shop. It made sense to me. The last thing in my mind would be a penis in between this girls legs. So I set up a date a simple dinner and a movie… Classic. I meet her for the first time and I was blown away by her beauty. She was all feminine and woman. No Adam’s apple, smooth skin, beautiful eyes. High heels and thick hips and a very feminine voice. Even her personality was that of a woman. I was really taken back and she really seemed into me right off the bat. We saw some transformer movie Idk which one. As soon as we sat down next to each other I immediately felt the sexual tension between us. I decided to pull a real smooth move by simply reaching over and holding her hand. I was eating Twizzlers so I gave her the first bite from one and then I had the next bite and so on. Until there was one bite left. She grabbed my hand with both of hers and then put my index finger in her mouth… Wow! No has ever done that to me before. We weren’t even past the trailers yet for the movie. I leaned in close and asked if she wanted to leave. Of she wanted to. We left the theatres and we made out in an elevator on our way down to street level. We hopped right in a cab and headed to her apartment. We were all over each other her hands kept going down my pants. I was running my hands through her hair and just holding her close. The cabby threatened to kick us out if we didn’t stop. It was one long ride with her hand down my pants. When we finally got to her place I carried her up to her apartment. As soon as we got inside we were making out. It was dark she pulled her tight dress up and off. As I kicked off my boots she removed her bra. Her body was smooth and smelled beautiful. She aggressively removed my belt and pulled out my cock and put it straight into her mouth. My God! The best blow jay I’ve ever received. She knew exactly what she was doing it didn’t take long for me to cum. I warned her I was but she didn’t even slow down nor flinch. She took all I had to give. My legs gave out on me. I had to sit down. She straddled me on the couch and we continued to kiss and make out. I was almost ready for round two when she decided to give a little strip tease dance. It’s still dark except for the faint light coming from her TV playing music. She takes her high heels off and does a slight erotic dance. I can’t take my eyes off her breasts and the shape of her body. Finally, she slowly pulls her panties down facing away from me. She gets down on all fours and turns around slowly crawls towards. She starts to give me head again. She gets me rock hard in no time. Then she says the most romantic thing any woman has ever said to me. “I want you to fuck my ass baby”. I almost came right. She pulled some lube from a nearby drawer. Lathers herself up, I scoot lower on her couch. She bends over and sits in lap. My cock slides right in her asshole I couldn’t believe how good it felt. My hands on her hips rocking forward and back. She is so tight I can really feel myself throbbing inside her. She puts her feet up my thigh and leans back on me. I thrust up and down inside her. She moans like a woman and turns for a kiss. I slow my thrust and place one hand on her breast while I assist her to turn to kiss me. At this moment I feel another orgasm coming. I felt a little guilty that I’m about to come twice and she hasn’t come once yet. So I reach between her legs to try and finger her but too much of my surprise I find a penis and balls. (Usually, I tell this part of the story where I leave ashamed that I had sex with a man). I felt so good and right. So I grabbed her? Penis? And decided to jerk her off as I would myself. I guess years of jerking off finally paid off because she got as hard as I am fucking her asshole. We kissed and I came inside her. I felt so good and I just wanted to repay Marjorie for giving me the best sex I’ve ever had. So when I pulled out of her I sat her down on the couch. I spread her legs open and kissed and licked her inner thighs from her knees to up to her ball sack. I sucked her smooth balls while I massaged her cock like the way I like to do to myself. When I put her? Cock? In my mouth, I never thought I would ever want it as much I did on that night. With every fiber of being, I just wanted to please Marjorie. I let her hold my head as she fucked my mouth. I wanted to take it. I loved it. I liked the gag her cock did to my throat. I wanted to really push myself. I never felt so alive! She said she was about to come but I was afraid to actually swallow so at the last second I pulled myself off her and jerk our cocks together and kissed her as she came on my cock. Afterwards, we were breathing heavily and we laughed together. Suddenly it sank in at what I had just done. I felt ashamed. However, we spent most of the night talking and we out for sushi. After we ate I went back to base. I never saw Marjorie again. I don’t know which I’m more ashamed of, having beautiful sex with an amazing person, who also has a penis, or never talking to that person again because I’m afraid of falling in love with someone who doesn’t have a vagina. What would you do? And what did think of my first ” tranny” experience?