Gay Grandpa Stories

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Infinite Scroll

Moving Day

by Jasonh007 on Sep 14, 2017
Erotic Couplings

I knew that Karen and Mark had grown very close over the last couple months, but when they decided to move in together, I was still shocked. It's not that I wanted her to move in with me-although we had been seeing each other for awhile, and sleeping together pretty regularly since that first night we hooked up at the party, I wasn't ready for that kind of c...

A Date to a Wedding

by Inthracis on Sep 14, 2017
Erotic Couplings

I had just moved to a neighboring state. I have some family in this state and a cousin was getting married. I did not want to go to this thing alone, since I did not know anyone yet beyond family, so I asked this female friend of mine (I am a guy) if she would be willing to go with me. It would be a chance to hang out since we had not seen each other in awhi...

This One Night in Orlando

by simplythatguy on Sep 13, 2017
Erotic Couplings

===== Everyone in this story was over eighteen at the time. This is my first story here and I hope to write more. Constructive criticism is always welcome. ===== I loved in Orlando for five years. I had a decent job but was also in a band -three, technically but it was just swapping a member here and there. That being said, I spent a lot of time in clu...

A Walk to Remember

by awantonangel on Sep 14, 2017
Erotic Couplings

That feeling you get when you think someone is watching you. That is the feeling I had when I was walking home the other day. I live and work in Washington D.C., a political hot bed yes, however, the town is over run with awestruck tourists as well. You can see it all as you stroll down the sidewalks or hop on the metro. At least during the day you can see e...

Me, Justin, & Halloween

by Church33 on Sep 16, 2017
Transsexuals & Crossdressers

I had a feeling my brother's Halloween party was going to be lame. I was right. Geek friends and high school drama club kids. I suppose that's why my parents even agreed to let him have it. He was a senior in high school and they knew by now that the kid couldn't get into trouble even if he fell head first into it. It was a chilly October so most of the cost...

My Decadent Friend

by Marlene on Sep 14, 2017
Transsexuals & Crossdressers

I have this friend named Carla. I met her through this other friend of mine named Jeff. Carla’s 22 now and Jeff’s been fucking her and getting her into all sorts of weird shit since she was fourteen or so. And I do mean weird shit! He’s had her in sex parties with her and a couple of gay guys and a couple of straight ones. He’s had her in all sorts of gang b...

Shopping for High Heels

by HighHeeledHoney on Sep 16, 2017
Transsexuals & Crossdressers

This is a short true story which although has no overt sexual content is one which many cross dressers may relate to. I began cross dressing many many years ago and found that I enjoyed the sluttier side of dressing - which you may be able to tell from my stories! I adore high heels (the higher the better!) and love the look and feel of both PVC and leat...

Margo's Weekend

by margobicd on Sep 14, 2017
Transsexuals & Crossdressers

Finally it's Friday morning and soon it'll be quitting time. I've been waiting for this day for 3 weeks. This morning I got up early and took extra time in the shower to make my body nice and smooth once again. I love the feeling of being smooth all over. Only an hour to go till quitting time, 60 minutes till my weekend starts. Finally I'm out of the office...

Seducing Jay at a House Party

by vhunt on Sep 16, 2017
Transsexuals & Crossdressers

Ann seemed pretty happy with the party she threw for her birthday. People were mingling in her garden, talking and laughing while they fought summer's heat with beer. I didn't know many of Ann's friends - in fact, the only face I recognized at the party was her own, but I knew she kept company with mostly single people and any of her gatherings resembled mor...

Diary of a Cross-dresser Ch. 01

by Adikon79 on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on my own personal experiences and any comparison or similarity to anyone else's story, experiences, or copyrighted material is purely coincidental. This story contains adult material and language and should only be read by those legally permitted to do so. The story within is the copyrighted material of the author and should not be redis...