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This is based on an approximate date of August 15, 2008 at 8PM as the last time I fucked my wife.

Friday, August 23, 2013

I Think One Of My Boyfriends Is A Crossdresser

"I think one of my boyfriends is a crossdresser."  Now that may sound like a strange way for a wife to start a bedtime conversation with her husband but for us, that would be pretty much normal.  "OK, what makes you say that," was my reply.   What she went on to tell me was he was pretty much hairless from the neck down, underarms, legs, etc.  He also loved rubbing her stockings or anything else silky and slinky she wore similar to the way I would rub her nightgowns and such is what she added.  Since I hadn't met this particular boyfriend she went on to describe him as about an inch taller than me, slim and nice looking but what she really wanted was her input on whether she should say anything or not.  What I advised her was not to approach it head on by asking but the next time she met him wear a really slinky nightgown.  If he was rubbing it like before to say lets have some fun and try to put the nightgown on him.  Well, she did and according to her it worked like a charm.  She said he resisted a little at first but caved in pretty quickly and then it was like he shoved an iron bar in her.  Then  when she knew he was getting close to cumming, she started rubbing his back through the nightgown and that was all it took.  He slammed into her and, according to her, started moaning along with shaking like he was freezing to death.  As they were laying together, she put her head on his shoulder and started rubbing her hand across his stomach through the nightgown.  She said he was usually good for two times but rubbing him got him ready in about half the time.  After they fucked for the second time, during pillow talk she told him how much him wearing the nightgown turned her on, something I had told her to say.  That broke down the wall and he told her he was a crossdresser which was the cause of his divorce.  His ex-wife had barely tolerated his dressing to start with and had gotten less tolerant over a couple of years.  Apparently the straw that broke the camel's back was when he asked her about his fantasy of making love while he was dressed.  She said she couldn't do it because it would be too much like lesbianism and that was the end of their marriage.  My wife, being bisexual had no problems with that and offered to help with makeup and such the next time they met.  She said just the mention of that brought on a third round of fucking with him cumming even harder than he did the first time.  Now let me interject here that my wife had helped me dress and done my makeup many times along with making love a few times with both of us in lingerie, makeup and such.  But she had never suggested or started it herself.  And of all the times I tried to initiate a little "girl" on girl with her, I had probably been turned down a lot more than she accepted.  But here she was volunteering to do so with one of her lovers.  I have to admit that I was a little bit hurt she would propose dressing up her lover for sex but I did understand it also.  My wife was helping "Deidre" to fulfill a fantasy as she had done for me the first time.  They planned their next meeting for a Saturday, starting at his motel room around 8 in the morning and, although she hadn't said so, I expected her home around 4 or 5 that afternoon.  She called though around 3 to let me know she would be very late and if it got too late she was going to spend the night which she did.  I found out the next morning she had gotten Deidre dressed casually and then went for a drive around town after dark.  They went through the drive-thru at a fast food place and got a couple of shakes, went out to the overlook at the airport and watched planes in the special parking lot there.  They even got out of the car for a little while.  Apparently it was the first time Deidre had ever been outside dressed and when the breeze hit her stockings, she almost went into sensory overload.(As sissies, we've all been there haven't we?)  That caused them to head back to the motel room for another round of sex.  They ended up the evening in nightgowns cuddled in bed and my wife said Deidre actually started crying thanking her for fulfilling that fantasy.  I have to say I was happy for Deidre when I heard that part.  Then I jokingly asked about the sex.  She laughed and said she had gangbangs when she wasn't as well fucked as she had been the day before and earlier that morning.  Once she got Deidre dressed on Saturday, they talked for a little while before they began a slow makeout session ending with a blowjob.  I know I've mentioned it before but my wife is world class when it comes to oral sex or as a couple of her biker friends have said, she could suck start a Harley.  Since Deidre and I were about the same size, she had taken along several of my dresses, skirts and blouses for Deidre to try.  They spent most of the afternoon trying on clothes interspersed with a couple of fucks before that evening drive and the nighttime sex.  Sunday morning ended up with another round of sex which of course caused me to want seconds when I found out she had just finished being fucked.  I didn't get it that day though because she said she was way too sore after Deidre had pounded her.  They didn't dress Deidre up every time they met after that saving it for about every third or forth time.  I guess they probably got together maybe 25-30 times over the next couple of years and eventually Deidre actually found a single lady who enjoyed Deidre's feminine side.  I was back to working out of town by then but my wife got an invitation to Deidre's wedding. 


  1. Very hot story. A lot more guys like wearing lingerie than will admit it.

  2. nice story wish i could meet your wife and you too

  3. I wish my wife would cuckold me and dress me in lingerie