Stories stockingluvr

2

An Introduction To Crossdressing, The Finale

As Jackie, Chandra and I finished up our food, we chatted about the evening yet to come.

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the...Read On

8

Fucking with the neighbor Paul

A continuation of the ‘Teasing the Neighbor’ series

For the next few weeks, I would visit Paul’s basement about twice a week for a dose of non-stop machine fucking. We would take turns tying each other down and letting the machine take us through multiple orgasms. We also enjoyed fucking each other’s faces and got quite good at deep-throating. This routine went on for about three weeks and at the end of our current session Paul said, “I have...Read On

4

An Introduction to Crossdressing, Pt. 6

As our evening progresses the fun continues.

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls...Read On

6

An Introduction to Crossdressing, Pt. 5

My first time at a not-so-straight club is friendlier than I imagined.

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in...Read On

6

An Introduction to Crossdressing Pt 4

Enjoying our continued weekend as crossdressers.

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my...Read On

10

An Introduction to Crossdressing Pt 3

After all the preparation I want it too bad to go out.

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any...Read On

9

An Introduction to Crossdressing Pt 2

Learning how to be a passable crossdresser

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The...Read On

9

An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole...Read On

7

Teasing the First Neighbor Again, Part 2

The morning after our latest round of exhibitionist fueled male sex I was feeling quite randy.

Waking with a rigid cock on a Saturday morning and no one to share it with was a bit of a bummer, but then I remembered my favorite dildo in the nightstand. After tossing the covers away, I got busy stroking myself while easing the dildo in all the way. It didn’t take very long before I was ejaculating all over my chest and stomach and feeling quite satisfied. I dozed off for about...Read On

13

Teasing the First Neighbor Again

It was time to get into the neighbors pants again.

I returned from the cabin late Sunday night still unsure how to have my way with Paul again, but I was sure something would come to me. Monday afternoon as I pulling into the driveway after a stressful day at work, I noticed Paul in his back yard talking to someone about his large old maple tree. Paul and I had talked about splitting the cost of having it removed as about two-thirds of...Read On

14

Teasing Another Neighbor

I saw Paul a couple of days later when he was out mowing his lawn and I was just getting home from work. After our night of spectacular but short lived sex in the back yard, Paul seemed a little more talkative. He mentioned that he really enjoyed himself and that he wouldn’t mind trying that again. I said that we’ll have to try something different as the best part was the spontaneity and risk...Read On

16

Teasing the Neighbor

I had an ever increasing desire to explore sex with another man...

I have always been an exhibitionist. As far back as I can remember I have always hated wearing clothing and always enjoyed being naked. Once I got my own place I wouldn’t hesitate to walk around the house constantly without a stitch of clothing. I realized that I found it quite thrilling that someone might catch me in this state of undress and take advantage of me, which only made me want...Read On

5

The Driving Exhibitionist

My exhibitionist side, along with my love of crossdressing, prove to be a great combination.

As much as I enjoy the sexual adventure that cross dressing provides me, I think my exhibitionist tendencies take it up a just a bit higher. Contrary to the promises of another meet by Officer Friendly and his wonderfully endowed friend it had been months since they had had their way with me. The lack of attention and the increasing darkness due to the approaching winter had me taking...Read On

22

Another Drive Home

Just when I thought it was a one-time thing . . .

It had been a few weeks since I had my fun with Officer Friendly. I had been looking out for him and had even called once and left a message but got no response. I wasn't too disappointed since I did get to fulfil one of my biggest fantasies, but still wouldn't mind another round. I did enjoy reliving the experience every chance I got by stopping at the parking lot where it all happened. ...Read On

31

The Drive Home

Relaxing masturbation on the drive home turns into something I've always fantasized about.

My commute to and from work is about 40 minutes each way. I enjoy the ride home the most as I use that time to undress from the waist down and enjoy some de-stressing. I always enjoy wearing stockings under my work day clothes and love nothing better than to get in the truck, hop on the highway and set the cruise control so that I can get naked. My office is about three quarters of a mile...Read On