28 I[M] Da[T]ing a trans woman now

So this maybe a bit long, and I’m going to sound like a complete hypocrite, but here it goes. I’m a pretty big guy, 6’2 about 180 lbs, physically fit, not a bad looking guy, plus chicks dig my job. Anyways, I’ve been going to my hair stylist for about 4 yrs now. She has her own salon, about 2 months ago, I walk in like normal, usually packed so I sign in, I sit at wait. She smiles at me and we have our usual small talk. She introduces me to her niece, who’s now working with her and says I should try her as she has about 3 ppl in front of me.
I immediately notice how attractive her nice is so I quickly say what the hell. She tells her niece take care of my favorite firefighter, he is my favorite customer. I sit in her chair, and she begins to cut my hair, we have small talk and what not and I’m kinda really digging her. She finished it up and then asks if she could take a pic and post it to her Instagram account. I don’t mind and asks if she can tag me which I allow. So that happens, 3 or 4 days go by and I decided to get on Instagram while bored at the station. I see the notification and click. I notice get profile and follow, I look at her pics and like fuck shes so sexy. I notice a few pics of her with LGBTQ shit, me thinking she was with one of her friends. Anyways days go by and I kinda stalk her profile. I end up getting drunk out one night with my friends at the bar and notice she’s posting to her story. I decided to slide into her dms, but I kinda did it discreetly.
“Hey, (we’ll call her amanda) are u free next sat, I really like the cut and wanted to make an appointment.” Amanda-“Yeah, what time did you want to come in?” Me-“Anytime you’re free, I’m sure you have a lot of clients” A-“Just let me know I’ll make time for you so you’re not waiting” Me-” About 1 ish? I get out of work about 9 am and tend to sleep till about then” A-“Sat at 1 is great ?” Me- “I’ll even bring you lunch ???” so from there we continue to text throughout the night, as I got more buzzed, I got braver and just told her how beautiful i thought she was. We were sending pics to each other (nothing graphic) throughout the night so I got the vibe that she didnt mind. Anyways I’m not going to lie, I got home and was stroking my cock to her pics, while texting her. I took the plunge and asked her out the next day. She kinda bounced around the question a few times and again I asked her out. She tells me she’d love to, but I may not want to, I ask why and boom she hits me with it. I had no idea. I don’t respond to her for about 10 mins, which was weird cuz during the night it was a few seconds to a min or 2 between messages. I keep looking at her insta and decided to say fuck it. I told her I still love to take her out.
I pick her up and fuck she was looking so good. Jeans which showed off her nice fat ass, nice tits. We end up at buffalo wild wings to watch some college football and have some drinks. It really eased the nervousness for me, I loved how she caressed my leg, would snuggle into me I’d wrap my arms around her. It was great. We were sitting at the bar, when I notice my co worker walk in, I’m freaking out, but trying not to show it. He sees me and comes over, we talk and he introduces himself to her and she played it really cool. We pay and decide to catch the last game at a dive bar. As we walk out, i’m holding her hand and open her door. As shes getting into the car, I pull her to me and give her a kiss, she puts her hands on my face and kisses me back. My hands go from her waist to her fat ass, culling both cheeks. We break the kiss, I spank her and she gets in my truck.
We get to the bar and chill for a bit, both having more drinks and my hands all over her ass. She asks if I want to go to her place for a movie, of course. We get to her apt, I’m buzzed and really into her so the nerves are completely gone. She goes to her room and comes back to her living room in a tank top, no bra, and some super small booty shorts. She sits right next to me on the couch. We put on a movie, but are more so making out. She ends up unbuttoning my jeans and whipping out my 8 inch cock. She is stroking it as shes lowering my jeans to my ankles. She gives me a kiss as she’s stroking my cock, she asks if I want her to stop. Omg fuck no baby. As I sit on the couch she lays across the couch with her head in my lap as she starts to suck my dick. Omg it was definitely the best fucking blowjob I’ve ever had. I play with her hair, put the TV on mute because I wanted to hear her slurping on it and wanted the continue seeing her suck my dick with the light from the TV. I have one hand on her head guiding it, my other hand on her back moving to her ass. I caress her ass, slide my hand in her shorts. Her ass was so soft, I tugged down her shorts with her panties, as she continues to suck on my dick. I caress her ass, sitting there enjoying the service shes giving me. My balls tighten and I can’t hold it any longer “baby, imma cum” i hold it for a few more seconds as she doesn’t stop. I shoot my thick load down her throat, she then cleans me up. I sit there a bit spent, she sits up and I notice her large clit, she has a small dick, which actually kind of works out, cuz that’s obviously not what I want. We go to her bed room and cuddle a bit, we talk about her head game and just have good convo for about 30 mins. I pull her to me and kiss her, she sucks my cock again and get me rock hard. I ask if she has condoms, she gave me one as she put it on me. She asks if I’ve ever had anal sex, I haven’t, she tells me to slide in slow and let her do the work.
We spoon as she reaches around and grabs my dick, she slides it in, I grab her hips and we rock back and forth a bit. I’m finally fully in her as I kiss her neck and back. We start to slowly fuck, she sounds so sexy. We end up in doggie, which drove me fucking wild, hands on her ass going to town. Then she rides me that’s where I lose it, she rides me till i cum. I was using a condom obviously. I’m going to sound like a hypocrite, I’ve never liked transgender people, i don’t mind the gay community, but i just feel that the transgender community tries to get everything catered to them. I’ve been consistently seeing her for about 2 months now, I’ve brought her around my friends, dates, people. Nobody knows, which is good, she seems to be okay with it. The sex is so fucking amazing, best sex ive ever had. I know I’ll probably get some shit talked to me, but who cares. I have pics of her. Kick me if you have any questions chriswhite1996

[MT] My girlfriend became my boyfriend, who became my biggest fetish

Three years ago I started dating my best (for all I knew at the time) female friend. We are a good match, so the relationship was pretty good. Our only problem was our sex life.

At the time I knew my partner had some deep trauma regarding sex, so we took our time. A year into the relationship we had a talk about our non existant sex life, which ended with my partner coming out as a trans man. After the initial shock, we continued stronger than before. My boyfriend is in a pretty shitty medical condition, so transitioning will probably never be an option. His family is religious, hence he is closeted and presenting himself as female for the time being.

So now I have a biologically female boyfriend, who to the unsuspecting eye is a hot pawg. It’s kind of an awkward situation sometimes, but I do my best to make him feel manly. Turns out we could never have penis-in-vagina sex because he hates his vagina. The next logical conclusion was “Dude if we are gay, shouldn’t we just do anal?”. Which was a great idea. Half a dozen of tries and two buttplugs later we were fluent in anal, and turns out anal is the best. It’s tighter, ribbed, and I can go way deeper. Doing it made him feel manly, which made him horny, and him being horny made me even more horny.

[M]y First Gay Bath House Experience with several [M]en

There I was, on my knees as two thick, throbbing cocks waived near my mouth. My hands gripping both of them… I start to stroke one while I guide the other eagerly into my mouth. The room was small and dark with only a faint red glow being casted from the lights above. The air was warm around our naked bodies as the three of us intimately embraced. I’ve never met the two men before I asked them to play, but that doesn’t matter… not in a place like this.

Roughly thirty minutes prior, I was sitting on the bed inside my AirBnb in Paris. It was 10:30pm when I decided to work up the courage to go to the closest gay bath house, which was only a 5 minute walk for me. Next thing I know, I find myself turning the corner down an empty alleyway. My heart starts to beat faster as I see the sign in the distance glowing bright. As I approach the door, I’m buzzed in. After speaking extremely broken French and nodding in agreement to the shirtless male receptionist, I was handed the key to a locker. I wouldn’t say that I’m fully comfortable being naked, but I found it easier than expected to strip my clothes. I grab my hand towel and head to the lower floor to start exploring. Surprisingly, my nerves begin to calm as I discovered what was on each floor. The basement had a sauna and jacuzzi. The first floor were lockers, a gym and the lounge. The second and third contained small, private rooms, dark rooms, glory holes, sex swings and a smoking section.

[MM] Massaged for the first time

Hi,

This is a real story, it happened about a month ago.

So… let me introduce myself. I’m not fond of stereotypes but just to give a context: I’m 31 and I consider myself as a straight cis-male. Never had any adventures with another guy, not attracted physically or emotionnally by men. However, I’m open-minded and totally non-judgemental (it’s not even a consideration to me).

I’m just out of a ten years relationship with a woman (married two years together), with a house to sell and everything, projects vanishing. I’m quite fine overall, but as you can guess, the past few months were a bit rough. That’s how, a month ago, I’ve had the idea of getting a massage to relax properly.

Actually, this idea was in my mind for a while now, being teased (and somehow “in control”) by a bi or gay massage therapist was quite appealing, I couldn’t really explain why; however I’ve always considered this as a harmless fantasy. Being single again though made me reconsider this. So I started looking on the net for local “massage therapists”, I was nervous yet turned on while going through all the ads. Didn’t want to go to any weirdo, the idea was to only be massaged, nothing more, but by a guy with experience.

[MM] – How I got my first boyfriend at 35.

I met Matt in 5th grade. I was new to school and he sat next to me in class. From then on, we were inseparable. During Jr High, we almost always spent the weekends together crashing at each other’s houses. In high school we were always partying together. In college, we were room mates. People used to call us JD and Turk because we were so close.

When we graduated college, life happened. I had to move a few towns over for a job. We got girlfriends and moved in with them. We stopped partying. We started talking less. I knew it was normal. This is what happens to adults, but I hated it. I found that most nights, I would have rather have hung out with him than my own girlfriend. Of course, I knew I had to keep that to myself. You don’t build good relationships like that. Plus, my feelings for Matt where always more intense than normal friend feelings and I had learned over the years how to suppress that.

[MF] fun night in the city with my Latina GF back in the day

So I thought I’d share some stories from back in the day. I’m pounding this out on my phone so excuse my typos please. Long wind up. Thanks for hanging in there

Back in college was dating this hot little Hispanic Chica. Loved her from the first day I saw her… Busty, short, curvy , great hair, great smile. Total spark plug. Fun and fiesty. I got to know her and we hooked up … she was DTF most all the time. As I later found out … without clothes it got even better. Short little hour glass. 32DD breasts with perfect nipples that tightened up and stood tall when teased, perfectly trimmed pussy… that instantly was wet, wet, wet.

Me, classic white guy. Dark brown hair. Not cut, but certainly not sloppy. 6 ft and 185 lbs. spose I look better with clothes on than off but oh well. my game is more about being smart, fun, a bit of a smart ass, and love to get various groups to party together. The more the merrier. Love adventure. Truth is I love women and I love women’s bodies … been told I’m “….an x-rated romantic”.

[MF] Fingering the Fiancée of a Feminine Frat Friend

This is a story about a public sexual encounter I had with a friend’s fiancee (more like acquaintance’s fiancee if I’m being honest – I couldn’t help myself with the alliteration in the title) in front of him at his birthday party.

*****

*Background*: I met Josh in grad school. The class sizes were small and we worked together on a few group projects, and so I got to know him decently well. I think Josh likes the idea of being a guy’s guy, but most would describe him as very effeminate – he is small framed, wears expensive flashy clothing, and speaks with a nasally, gay lisp. Many of my gay peers jokingly expressed relief that there was someone ‘gayer and more flamboyant’ than them in our class. Josh was extremely sensitive about his masculinity and sexuality, though, often giving knee-jerk reactions to any jokes that might even insinuate he is gay, and talking about sex and women (reminiscent of scenes from The 40-Year-Old Virgin) or about cars and hanging with his frat bros. I don’t want to get too far into armchair psychology, but it really seemed like an unfortunate case of bad case of repression and a lack of self-acceptance.

An Underground Club and Public Sex [MF][MFF]

Last week, Stacey started talking about this club some of her co-workers have been hitting up. I’m game for anything, but Kate wasn’t up for it. She told us to go, and specifically said if either of us were gonna hook up with anyone we were allowed, but be safe.

I asked her what the vibe was and she said it was one of those speakeasy style places where you dress like the prohibition. So, we watched some YouTube tutorials and put together some outfits and headed out. We get to this shady place in the warehouse district. If it wasn’t for the cars being mostly fancy af and there being a valet, I would’ve bolted.

We get to the door and it’s a legit slide the port open and ask for the password thing. Stacey told him that night’s password (Hocus Pocus), and he let us in. So, what I gather is that these popup places get some social media influencer types in for free, tell them the password, and they spread it. We get inside and it looks fantastic. Edison lights, the bartender in a hipster mustache, young upwardly mobile people having a blast. The music was good, too. The right amount of modern indie hits with big band flavor.

I was in a polyamorous relationship. Part 4 : An orgy to remember. [GROUP]

I had partaken in many orgies with Brian and Derek, but this is the one I enjoyed the most.

It was like any other weekend with the boys. I woke up to Brian’s tongue in my pussy on a Saturday morning, sucked both Brian and Derek off, had breakfast with them….. you know, the usual. Brian had told me the day before that they would have a bunch of guys over for a sex party, several of whom were into women, as well as men. I was in, obviously.

In the early afternoon, the guys began pouring in. I had met and fucked some of them before. There were nine guys there, including Brian and Derek. Two of the men were gay and they had made it clear that they wouldn’t do anything with me (I was glad to have gotten this out of the way).

We had moved the living room furniture into other rooms and had laid out several mattresses on the floor. Bowls of condoms and tubes of lube were placed strategically around the room and the stage was set for a glorious sex marathon.

[FF]ucking my tiny, slutty friend for the first time. [Long]

So this is a write up of the beginning of a year and a half of very good (and occasionally kinky) sex with someone I consider a very close friend. We recently stopped seeing each other because she moved away, but I wanted to memorialise this intense period of my life and thought it might be worth sharing. I put a marker for where the sex starts. Hope it makes sense.

——

I noticed Yasmin immediately as I walked in to the classroom on the first day of the first semester of university. She had just finished making herself a cup of tea in the kitchenette in the corner, and as she turned back to sit down, her dead eyes (resting bitch face in all its glory) glanced in my direction as I stood in the door, looking me up and down. Her face was beautiful but cold and I made a mental note to keep clear of her, I had just gone through a drawn out breakup with my live-in girlfriend and I was looking for ^good vibes^ only, no drama and all that Tinder bio crap that you believe when you want to make changes to your life. I sat down a few rows behind her next to some guy and did the usual small talk before the orientation session began. As it started, I found myself watching the back of her instead of the slideshow, and began to take the rest of her in.