My [F] first tranny [TF]

There’s a tranny chaser up in here…

It’s me. I’m the tranny chaser. My entire sexually-active life I’ve had a very distinct interest in all things gender bending, androgynous, trans, drag, and cross dressing. I know very specifically what I’m into and it’s hard to make the stars line up in my favor. But, it finally happened. She contacted me as her male self on Plenty of Fish, which on my profile states I’m into TS/CD so she felt comfortable telling me right from the start she was a cross dresser with interest in going full-time. I’m feeling it. I’ve had men approach me before that cross dress in the bedroom, just lingerie and panties… that’s not my deal. I mean, I like those things too, but I want it to be more than just a sexy bedroom activity. Like fisting, or crying about my dead father. Read more »

[MF] a week of spanking and sex: Sunday (pics)

Angela: five-six, about 150 pounds, around 30 years old. Long brown hair, dark brown eyes. Soft all over. Her breasts are probably a C or D cup, but I don’t remember exactly. She has children, and when she’s naked she’s completely unselfconscious about the changes that having children made to her body. I think she’s gorgeous and sexy. Oh, and she’s a squirter, too. Every single time.

Me: Six feet tall, about 290 when this occurred, mid-30s, brown hair, blue eyes. My hands are pretty large. That’s about all you need to know.

[Tuesday](https://www.reddit.com/r/gonewildstories/comments/58jemg/mf_a_week_of_spanking_and_sex_tuesday_pic/) | [Wednesday and Thursday] (https://www.reddit.com/r/gonewildstories/comments/58ptvi/mf_a_week_of_spanking_and_sex_wednesday_and/) | [Friday](https://www.reddit.com/r/gonewildstories/comments/58ybt1/mf_a_week_of_spanking_and_sex_friday_pics/) | [Saturday](https://www.reddit.com/r/gonewildstories/comments/5971wu/mf_a_week_of_spanking_and_sex_saturday_pics/)

I really wanted to have sex with Angela one more time, and had plans to do that when we got home, but Angela had other ideas.

“I want you to spank me until I safe-word, or until I’m crying too hard to say my safe-word.”

The sheer amount of trust in that statement is staggering, and given that I thought the week wasn’t going as well as it could have, I never thought she would ask for that. But she did, and all thoughts of sex exited my brain. I could have sex with other people, but not many of them would make that request. Read more »

How I [M] Got my Ex [F]

I was 19 at the time and average looking guy. Weighting 150 lbs for 5’9″ and she was probably 120 lbs for 5’6″. It all started during college in one of my classes. I noticed how pretty she was, she had those dark hairs, voluptuous boobs, small belly, good waist and nice ass. Ohhh that ass. She had also the prettiest smile I’ve ever seen and she had a small space between her two front teeth but it’s what made her special.

So we met during a small in class teamwork. She was alone and I asked her if she wanted to join us for the task and she accepted. After the work was done, we talked til the end of the class and we really clicked. I didn’t it through and after the class was over, I just said goodbye and left. The next class, it was my turn to be alone and she offered me to join up and I accepted. This time, after the work was done, we both added each other on Facebook. We chatted during the weekend and as I was showing her to my sister to have a feedback (I was really self-conscious at the time), I noticed she deleted me from her friend list. When I asked her why, she told me that her boyfriend didn’t want us to talk, even though we weren’t saying anything bad because we were trying to know each other. But she didn’t tell me she had a boyfriend so I was really surprised of this and stepped down by respect. Read more »

Never thought LARP would lead to this [Group]

Apologize in advance for the fornatting. Writing this on my phone in a moving truck at work. Also there are like 9 people involved here so I’ll put up a short description first.

Me (31/m) tall, awkward, gangly, short spiked hair

Nick (30/m) toned muscle, 0 body fat, GQ coiffed

Adam (27/m) thick but muscled, ponytail

Abby (28/f) tall, skinny, goofy but sexy, kinky curly hair that,would reach the floor if she ever straightened it.

Sam (29/f) average height, bit thicker but in all the right places. Amazing tits and ass, medium length dark hair.

Maddy (25/f)

Dee. (22/f) small, short, slight, looks like you’d break her just by looking at her.

As stated previously, I am an avid gamer, and have spent the last two years with an incredibly fun, tight-knit group of Werewolf the Apocalypse LARPers. My in-game pack have really become like family to me, except for my actual RL brother, oddly enough.

Flirtatious, perverted, sexually charged family….. so maybe the metaphor falls apart pretty quick. Unless you’re into that sort of thing. Read more »

Tinder Date [M] [F] [NC] [tease]

I met Jen on Tinder a few weeks ago. We’ve been on a few dates and have always had a good time, although we’ve never sealed the deal if you know what I mean. Tonight, we grabbed dinner then went to a small club to go dancing. Jen looked sexy as hell tonight, her large breasts were bursting out of her low-cut top, and her skirt hiked up high on her thigh as she walked. She has a gorgeous figure with a little waist and a curvy ass.

As I’m driving us back to her place tonight Her hand is high on my thigh, just barely brushing the side of my cock and balls. I shift my weight a bit and pull her closer, she knows exactly what she’s doing and she knows what I want, she is such a tease. Finally I pull up to her driveway and pull her in for a kiss. We’ve been on 4 dates now and I can’t take much more waiting. I need to feel myself inside her, to taste her, to see her beautiful lips around my cock. She reciprocates the kiss, and giggles shyly. I unbuckle our seatbelts and slide my seat back. She coyly climbs over onto my lap, straddling me, kissing my neck. Her skirt is hiked up high now and she is grinding on my cock through my jeans. I need this release, I need her mouth, I can’t take it much longer. I put my hand between her thighs but she quickly bounces off of me and back to her seat. “I had a great time” she says, as she goes to leave the car. What? I suggest going up to her place but she says she wants to take things slow. Ok, I take a deep breath and say my goodbye’s. Read more »

Our first threesomes [MMF][MFF]

So my BF and I have been together for 5 years now. I’m 24 and he is 25. We have a very good communication when it comes to sex and in general as well and I would describe our relationship as spicy (from anal to squirting we do everything). He has been the one bringing up most of the topics but I ended up always saying yes and actually sometimes being even more desperate to try. For instance he actually said we should record ourselves but I was the one taking the camera the first time. He said we should put it online and I actually created our amateur account on some famous site. Anyway, that’s not the point.

Two years ago, be brought the topics of sex with multiple partners, that is going for MMF and MFF and even just fucking with other couples. At first I was a bit shocked but then I kinda understood him but the project stayed a project till very recently. Both of us wanted it but both of us also knew we would be jealous and we would not stand it.

But we figured out that we could probably do it anyway. That’s how we proceeded. Read more »