tagTranssexuals & CrossdressersCrossdressing Playdate at the Lake

Crossdressing Playdate at the Lake

bymontrealjane©

At the end of the summer, I was lucky enough to have some playtime at the lake. I had been emailing and IM'ing back and forward with a girl that I had found on Craigslist. Craigslist is something of a lottery full of timewasters and scary people using many bogus identities, so it takes some time to filter out who really serious to get together and have fun, and who is just fishing for pictures or jerking off to emails.

Eventually she seemed to be real. Karine was visiting from Southern Ontario and had borrowed a condo on the lake that we could use to meet in. It was early September, so it would not be too busy, but the weather was still warm. I have always played before in saunas or a motel room, so I was excited to go to a condo for the first time.

The place was an hour or so north of Montreal. I don't like to spoil the atmosphere by meeting before we are dressed, so we had agreed that when I knocked, the door would be open and I should go in and go to the spare bedroom so that I could get dressed before we saw each other.

I had brought a few outfits with me. i showered, and took my time getting ready. See through G-string, garter belt with stockings, padded bra, heels (not too high) with a black babydoll nightie. I put on my favourite blond wig, and neatened it up, and some lipstick. Dark glasses, just because they make me feel gurly. I am not shaven, and certainly not passable, but I checked myself in the mirror, and with clit bulging in the g-string I didn't think I looked so bad. I went out to the main room to meet my girlfriend for the day.

Karine had sent me some pictures, and she certainly didn't disappoint me. She was slim, totally shaved and wearing a leather dress with stockings. Nice hair and beautifully made up, I knew that it was going to be a good day.

We exchanged kisses, and she offered me a glass of wine. We sat on the couch and it wasn't long before we started to explore each other. While I sat down, she gave me the hottest lap dance I have ever experienced. Her ass looked fabulous under that leather dress. She would let me touch her ass, but I had to keep my hands off the clit as she teased me. She pulled the dress up showing me the outline of her clit under her thong, but wouldn't let me touch. I was rock hard, and she was obviously enjoying herself. She sat astride me, so my hard clit could feel hers through the fabric. My hands were all over her.

She took my hand and led me to the bedroom, and she went into the bathroom to change. Still in the stockings, she now wore a long see through nightgown. I lay back on the bed as she continued the show standing over me. Still wearing the thong, she teased me rubbing her hard clit against mine, and kneeling over me rubbing it gently against my body, and then letting me lick it, again through the fabric, but not allowed to touch it.

Then it was my turn as I made her lie down on the bed, and teased her with my clit. I pulled the g-string aside and stood astride her letting her see it as I knelt down and lowered it into her open mouth. We were soon 69ing as my hands explored her curvy ass.

For the next half hour, we played with each other, sucking and stroking. She lubed her pussy, and I put on a condom. She opened the mirrored closet door so it was at the right angle, and she got on her knees at the end of the bed, as I stood and entered her pussy. I could see in the mirror as she jerked herself off as I fucked her. It didn't take long before I shot my load, and went round just in time for her to come on my face.

We rested on the bed, before we went off and showered separately and changed. She came back wearing a bikini. I wanted to enjoy the day relaxing in lingerie, and had put on my favourite one piece lace romper. We had lunch, and had some wine and relaxed on the couch together in the sunshine. The sliding doors were open to the balcony over the lake, but unfortunately we couldn't sit out on the deck where the neighbours could see.

After lunch, Karine put on some shemale porn on the DVD to get us back in the mood, and she went and changed into another outfit. This time a latex bustier and panties, and leather thigh high boots. Again she started to tease me. I was soon rock hard, and I got the second sexy strip show of the day. This time, I wasn't long before she unzipped the front of latex panties and pulled her clit out for me to suck as she stood over me. I sucked her gently, stroking and teasing her clit all the way back to her pussy. Then it was my turn for the same treatment. she put a little lube on her finger and found my g-spot in my pussy while holding me in her mouth.

We moved again to the bedroom, and her final outfit of the day. A pink babydoll with matching open crotch panties. She looked so fucking hot. Now that she was out of the latex and a real girly girl, she told me to take charge and fuck her like a sissy bitch. I put her on her back at the end of the bed, condom and lube and sunk myself in her deep. She let out a slight squeal, as I held myself still all the way in her pussy. I jerked her clit as I held myself still until she shouted for me to fuck her hard. She came almost right away, and shortly after I was ready. I pulled out and came all over her face as she tried to catch drops in her mouth.

We lay on the bed in our lingerie and hugged for a while, before kissing goodbye. I went back to my room and showered and changed back to my regular clothes before heading back to the city, making sure that we didn't see each other when not dressed as Karine and Jane.

We haven't seen each other since, but we both have the intention of repeating when she is back in Quebec.

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by Anonymous

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by Anonymous02/24/14

Hot

A perfect playdate

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by RebeccaCherie02/19/14

Stunning

Stunning Jane.
Adream come true.
I soooo wished I had another boy to play dress up with when I was a teen.
Xxxxxxx
Rebecca

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by Anonymous02/15/14

great fun

Looking forward to more playtime!

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