[MT] My first time with a transwoman, part 2

If you haven’t read [part 1](https://www.reddit.com/r/gonewildstories/comments/8zxq39/mt_my_first_time_with_a_transwoman/) of this story, I encourage you to go do that now. To those of you that have read the first part and encouraged me to write this, I’m not sure it lives up to the first part but here it is all the same.

As I feel my energy returning, I start to plant kisses on her skin. I make my way down to one of her nipples and take it in my mouth. I suckle on it and flick my tongue across it. She moans in response. I gently bite it and she yelps. “Bad boy!” She playfully swats me on the head.

The fire has started to die down and will be nothing but smoldering embers shortly. I test my legs to see if they’ll hold my weight again. They seem to be back to normal and so I stand up. I offer an outstretched hand to the vixen kneeling on the deck and help her up. Continuing to hold her hand, I start to walk to the sliding glass door to take the party inside. She doesn’t follow me. I turn around and she says she wants to stay out here under the stars. I shrug, close the distance between us, and begin kissing her. By the time we break the kiss, we’re both a little out of breath. She wraps her delicate fingers around my cock, starts slowly stroking it, and says, “My turn?” I nod and she squeals a little bit. She goes over to her bag, pulls out a bottle of lube, hands it to me, and then goes over to the railing of the deck.

[MT] My first time with a transwoman

As a disclaimer, I know it can be a touchy subject so if I say something wrong or don’t properly respect what it means to be trans, I’m sorry but I’m still new to this. I’m going to try my best to be respectful but if I fail in that, please don’t go apeshit on me.

After Emily and I broke up, I was kind of a mess for a couple months. I was 31 years old and I realized I wasn’t getting any younger. I wasn’t 20-something anymore and my body reflected that. I felt disgusted with myself and my life. Practically every day on my Facebook feed I saw all my friends out living life. One friend was backpacking across Europe, another one was surfing in Hawaii while someone else was posting pictures of their visit to Turks & Caicos. Many others were celebrating anniversaries, marriages, or the birth of a child. The whole time I was living in my parent’s house with no one to share my life with. I had a job making good money but it still only paid my bills while leaving me with a couple hundred dollars a month for everything else.

[MF] [Cuckold]-ish? Emily gets fucked by “a real man”

I really enjoyed sharing the story about my last night with my ex, Emily, so I figured I’d share another story about her and I. You can find that story in my profile. I’m trying to keep things short but I like to be descriptive. Sometimes I end up just being long-winded instead. I’m working on it.

As I mentioned in my previous post, sex between Emily and I has always been pretty intense, fairly rough, and even a little violent at times. I didn’t really make much effort to describe Emily or I in my previous post so I’ll do that here.

At the time of this story, I’m 30 years old. I’m 6’ 4” tall and I’m definitely rocking a bit of a dad bod as I weigh around 275 lbs. My brown hair is naturally curly, so much so that women constantly fawn over it and talk about how it’s going to waste on a man’s head, but I keep it cut short because I’m a man and I hate dealing with it. I’ve been described as barrel-chested. For the most part my eyes are a blue-gray color though my right pupil has a small bit of brown in it. As for my cock, it’s about 7” long and I can barely get my index finger and thumb to touch if I try to get them around it.

[MF] The last time I would see her

I’ve enjoyed reading everyone’s stories here on gonewildstories so I figured it was time to give something back. It’s about the last time I saw the woman who would completely turn my entire world upside down.

I met Emily at work. We hit it off immediately. I was 30 at the time and she was 33. I’m 6’ 4” with short brown hair and gray-blue eyes. I wasn’t in the best shape of my life when I was with Emily but neither was she. She was 5’ 3” and was a bit on the thicker side. I wouldn’t say she was fat but she was kind of getting there. She had two kids from her first husband and was currently in the process of divorcing her second husband.