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gerry15
1 month ago
Bi-curious Male, 62
0 miles · Minnesota
Profile Stories
11
Ebooks Friends
184
Follows
157
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550
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Stories

Series
stockingluvr

Lila Makes Three

Very quickly, Lila became a wonderful addition to our family.

Lila The 'cleaning' continued as Gerry and Jim brought me to a warm-water climax in the confines of their wonderful shower. Gerry was busy tonguing my ass from the beginning and agitating my clitty with his fingers. As if that wasn't enough, Jim chewed and bit my impliable nipples like it was the first set he'd ever seen. I wailed into the downpour as my new two favorite men brought on a climax like I hadn't felt in far t...

stockingluvr

Very Good Friends - We Add A Third

After some amazing sex, Lila opts to come home with us.

Gerry In the aftermath of our wonderful threesome, Lila and I worked to bring Jim's waning cock back to life as he lay on his back. We were facing each other and taking turns lapping at his scrotum and sagging pole. "You do know that you have an amazing man, right?!" Lila whispered. "Very much so!" "Good, because I have to tell you that I could easily fall for him. Not that I would ever try and steal him from you, but rat...

stockingluvr

Very Good Friends - Adding Another

Nearly a year into our relationship we were ready for something more.

Jim Gerry and I had been dating for nearly a year now. I was staying over at his house during the weeknights, and he came to mine on the weekends. The sex was still quite good but was starting to get a little bland. We'd begun trying some different things, such as hitting the clubs once or twice a month, but neither of us were really into all the excessive noise or the rudeness of some of the people. We scoured the nearby...

stockingluvr

Very Good Friends - Continued

The evening brings us much closer than either of us had anticipated.

Jim Turning around, Gerry came back and kissed me while cupping my groin and giving it a squeeze. He led me through the back door and around toward my car. After one more kiss, he suggested, "How about I meet you at Fratellis in about an hour. I need to rinse off the sawdust and change into something a little sexier." "Okay, but you better not stand me up, or I'll come looking for you." "No chance of that!" he grinned bef...

stockingluvr

Very Good Friends

Our friendship deepens quickly and reveals a few surprises.

I'd moved my print shop to a new location across town recently for a cheaper and more long-term lease. One of my first customers at the new place was a guy named Gerry. As we spoke, I found out that he was the owner of a small business as well. Gerry was a cabinetmaker and created some primo custom-built cabinetry. He'd come in to get some updated cards and stationery and wanted something with a little more pizazz than hi...

gerry15

Noticed By A Woman

Standing outside for a cigarette I was noticed.

I sat behind the steering wheel buckling my seatbelts. I turned the key and looked at the clock as the engine came to life it was 3:20 am as I pulled the shift lever into drive. 850 miles and 16 hours later I pulled off of I75 north of Nashville to a small town called Cadiz. I was through three states and into my fourth. I was in Kentucky and needed a room for some rest. I stopped at a Quality Inn. Parked the truck and tr...

gerry15

Masturbating for my client's neighbor.

Working on a clients house crossdressed.

It started as a very routine Thursday morning. I loaded my truck with the tools I knew I would need for the days work as well as a sexy outfit to wear while I worked.  My wife was working from home as the Covid19 virus had forced her office to keep all employees working remotely. It had been a few days since I dressed and I was urning some fem time. I finished loading my truck and drove the four miles to my client's house...

gerry15

Lunch Date With Clair

My lunch date with Clair turns out to be a lot more than a date.

It was Tuesday morning and I had a rheumatology appointment in Maple Grove at 10:15 am. It was now about 7:30 and I thought I should start getting ready for my appointment and lunch date I had set up with Clair. When I talked with Clair on the phone last week, we decided an early lunch date would work for us. She told me to meet her at Biaggi's at 11:30 am and that she would be waiting. I jumped into the shower and shaved...

gerry15

Meeting Clair

Going shopping for pantyhose.

I was on my way home from the Minneapolis metro area. I was going right past the outlet mall and need to pick up some pantyhose to replenish my supply. I wear pantyhose everyday since I had my varicose vein surgery. The doctor suggested that I wear support hose to keep the problem from coming back.  The nurse at the vascular surgeons office suggested that I wear Hanes Alive pantyhose as they were the right compression and...

gerry15

Practice Pays Off

First time out in public dressed as a woman.

It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time. I got out of the shower and was nice and clean, smoot...

gerry15

masturbating for a woman on a video site while crossdresing

I was messaged about one of my photos on my bio by a woman, she thought it was very erotic.

After years of crossdressing I joined a site that lets me show off a little. I started by reading the stories and then filled out a profile. I added pictures and found it quite satisfying getting comments and friend requests from others.As time went by I found myself enjoying chatting with others on the site and doing some role playing. The chatting was hot and I really liked sending pictures of myself to those who seemed...