So Jess and I met in high school during some youth group stuff. We had an instant connection. She was very quite and reserved, but on her own she was wonderful. At that age we only kissed, but we both wanted much more.
We kept in touch over the years and chatted all the time. When we both got to college we tried to meet up at some point and give in to all of our urges, but we didn’t get a chance to. We sent pictures back and forth to each other and watched each other mature through the years. By the time she graduated college (2 years before me), she had put on a little weight, but still had a face that was cute as ever. She was about 5’4 with brown hair and like a said, a little chubby. She had always had big boobs, but now they were absolutely enormous. We had phone sex and would write each other sexy stories. It was always nice to come back from class and see an email with a story from her.
So a few more years went by and Jess fell in love with a guy. It got super serious and our romantic relationship came to a screeching halt. She ended up marrying the guy (Let’s call him Zac) and we essentially stopped talking. It was a tough spot to be in, but it would have been hard for us to separate our naughty thoughts from every day conversation.
So 5 more years go by and I run across some old pictures and find a picture of Jess and I and a few other friends of ours. Suddenly I am over come with finding out what ever happened to Jess. We never became Facebook friends or anything like that. So I try to find her on Facebook and had a really tough time, but I was finally able to track her down. I shot a DM just saying hi and that I hoped all was well with her.
A full year or so goes by with no reply. Then one day I get a message from her saying that she never thought she would ever hear from me again. I was surprised to hear from her after a year, but also excited to catch up. So we trade a bunch of messages back and forth and find out the following things have happened over the past few years: she got married, had a kid and ended up divorcing Zac. The final thing I she told me really threw me off. She came out as a trans-man who was still interested in men and also had no intention of transitioning. Understandably, I was quite confused, but curious.
I asked lots of questions. Some were quite sexual in nature and she rebuffed those questions. She didn’t want to go there and for the sake of our reconnection, I agreed. So we talked a lot over the next few weeks when one day things took a turn. She started off the conversation about how horny she was. Then things dove into a sexual discussion.
She told me she had dealt with a lot and it has caused her a lot of difficulty mentally, emotionally and physically. After the sexual talk, we felt we could exchange some pictures. I was surprised to see her in the first one she sent me. She had lost a lot of weight and cut her hair. Now she had a pixie cut and was now skinnier than when I first met her. However her boobs remained the same size.
So things continued to escalate and finally got to exchanging some nudes. She was the one to send one first. Her hour glass figure was still a bit chubby, but her tits hung just perfectly above her little pooch stomach and trimmed pussy. She had a cute little smile accented by her thick rimmed glasses. Then it was my turn. I was rock hard after seeing her picture. I turned at a 45 degree angle in the mirror and snapped a photo making sure that she got a good view of my cock and ass. I sent the picture and awaited a reply.
About a minute later, my phone rings and it’s Jess.
“What the fuck?” she says.
“What do you mean?”
“That’s not really you right? You photoshopped your face onto that body right.”
“No that is me, I just took that picture.”
“Oh my god! I can’t believe you have been hiding that from me this whole time” she says as she begins to moan a little.
“I’m glad you like it!”
As I finish talking, I hear her moan a little louder. She was now masturbating while we talked.
“I think you need to come out to Colorado and see me now” she says talking through the moans.
So I looked at my schedule and found a time to get out there. I flew out and met her on a Thursday. I took a car to her apartment as she was working and couldn’t come get me. She opened the door and planted a huge kiss on my lips. Then she pulled me into her place. We separated and admired us both standing in the same room for the first time in many years. It was amazing to finally have my arms around her amazing body.
After that we wasted very little time getting underdressed. Her body was even better in person. Her tits dropped like pendulums out of her bra and my cock shot up in the air after clearing my pants. We raced back to her room and onto the bed. We started to make our furiously when she suddenly stopped.
“So you know now that you will be having sex with a guy, right”. She says.
“Yes, I am quite alright with that”
With that, I rolled over on top of her and entered her. She was the wettest pussy I had ever been in. I sucked her tits while I went deeper and deeper into her pussy. After only a minute or two she screamed that she was cumming. Which was good because after all of this build up, I was getting ready to cum too. I pulled out and blasted a load that reached from her stomach all the way up to her tits.
After all these years we were able to connect, but definitely not under the circumstances I thought would occur.
Source: reddit.com/r/gonewildstories/comments/c5vb8a/first_time_for_everything_mt