This story requires a short preamble. I had e-mailed erotic stories and fantasies back and forth with my friend Paul for several months. He liked to be a dominant, so one day I asked him to send me exacting instructions on how he would like me to masturbate, which I would have to do and then describe back to him. He sent the instructions, which involved me getting fully cross-dressed before sitting down to watch a particularly hot she-male video, and about a week later I was finally able to carry them out.
The following day I wrote it up and e-mailed it to him. Unfortunately, Paul read my write-up just before leaving to pick up his girlfriend Tracy on a date. Reading the details of my carrying out his instructions had him so horny that instead of long relaxing sex after an evening out, they had fast and furious sex almost immediately upon his arrival; with her, bent over the kitchen table, panties down, skirt flipped up. Although she admitted to getting somewhat of a kick out of it, she also felt slightly cheated in the deal. I wrote this story for her as an, "I'm sorry." Paul tells me she loved it!
This one is for Tracy
Having learned of Tracy's disappointment with me, as I had stolen the thunder from your date evening, I called her and asked if there was anyway I could make it up to her. She thought for a moment, then said, "come over here tomorrow around 6 PM, bring your best female lingerie and whatever dress is the closest to a maids outfit, some toys and lube."
Reporting as ordered, she led me into a bedroom and made me change, while she watched, into my stockings, garter belt, thong, bra, wig, heels and black mini dress. Once satisfied with my appearance she asked, "what toys did you bring?" I showed her the selection I had brought. "Lube the butt plug…. and put it in, then meet me in the kitchen," she said.
As soon as she left I lubed the butt plug up with the KY and added a little more on my finger, hiked up my skirt, pulled the string from my thong aside, lubed my butthole up and gently slid the slim but plug in, then replaced the thong string.
Once in the kitchen, I was ordered to clean up, using an upright vacuum of which I was instructed to keep the vibrating handle against my crotch the whole time. Tracy watched and giggled, I'm not certain whether because of the awkwardness of trying to vacuum while holding the handle in place or the fact that she knew the vibrations were very pleasurable on my cock, or perhaps it was my unsteadiness on my 3 inch heels. After that chore was completed I was forced to strut around touching up all of the high shelves with a feather duster. Again, this brought more giggles as my mini dress was constantly lifting up, exposing my bottom. Eventually the cleaning was done and I was ordered to serve her tea at the table.
As I stood by, she sipped her tea and, slipping one hand up under her dress, said, "bet you would love some of this pussy, well you're not getting any, just like your e-mail, you will just have to admire it from afar," she giggled as she pulled the skirt up to reveal that she was panty-less. My infatuation with the view was interrupted by the doorbell, "please get the door Jesse," she ordered, politely. I opened the door gingerly, fearing a stranger seeing me all dressed up, and was pleasantly surprised to find a familiar face, "hello Paul," I said as I opened the door wide, "please come in."
Watching from the kitchen Tracy pushes her chair back from the table, slides forward a little bit on it and looks our guest in the eye as her fingers strum across her pussy. "Jesse, go in the other room and remove your butt plug, then return with the KY jelly," she says with a little movement of her head indicating to go. I do as I'm told, making sure to straighten my underwear and dress while in the other room.
Upon my return I am surprised to find Paul standing with his pants around his ankles, stroking his cock while watching Tracy play with herself. "Jesse, lube Paul's cock, now," she tells me; as her face starts to show some signs that the fingers are doing their job. Not being certain of what is going to happen next I generously lube the hard cock offered to me and make certain to stroke it to its full hardness.
Now Tracy looks me straight in the eye, "bend over the table bitch!" Caught off guard, I quickly start looking for the proper place to put myself. "Bend right over the other end of the table," she commands, "you are going to get what I got, fucked by somebody thinking of someone else, let's see how you like it."
Bending over the table and looking at her, I feel the mini dress has slid up, "do her Paul, do her like you did me that night," she said smiling. I feel the dress being pushed further up and the string of my thong being pulled aside, my ass cheeks gently being moved apart, and then the head of a cock, where moments before the butt plug had been; I try to relax as I feel it pushing in and then enjoy that wondrous feeling as my sphincter clamps around the shaft, "ohhhhhhhhhhh," I moan.
"Watch me Paul," Tracy says as she's fingering herself furiously, "watch me as you fuck that bitch, use her ass like you used my pussy."
I feel the rhythmic thrusting in my ass and keep watching Tracy, unfortunately from my position I can't see her fingering her pussy, although I can see her arm moving. But I can sense that all eyes are staring at her and it is very obvious she is geting close, "mmmmmmmm, yes, yes, yes, keep fucking her, use her ass, yes watch me, you can't touch me, but watch me, think about me, fuck her deep while you watch me, watch me, watch mmmmmmeeeeeeeeee…….." she half screams while bucking off of the chair in a huge body wrenching orgasm.
After a few moments Tracy regains her composure, looking up she says, "pump that load in her ass!" I feel the thrusting accelerate and the hands that are on my hips pulling me harder back onto the shaft of the cock that is pounding into my ass deeper and harder until I feel a hard final slam and the hands on my thighs pulling me even harder and the cock spasms and spasms and spasms as it spunks it’s load inside of me. Eventually, the cock goes flaccid and is withdrawn, leaving me to wonder what is next. Tracy looks at me, "did you come yet?" "No ma'am," I say standing up to show the hard on bulging against my panties. "Remove your dress and panties then lay on the floor," she tells me. Again, I do as I'm told. She walks over and straddles me, hiked her skirt and again buries her fingers in her pussy, "stroke yourself off," she commands. My fingers start furiously flogging my cock, which is aching to cum and within moments long creamy streaks shoot across my belly and bra as I let out a huge moan. Tracy looks down at me in giggles, "now we are even, but I've got more plans for you."
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<a href="https://www.lushstories.com/stories/crossdressing/this-one-is-for-tracy.aspx">This one is for Tracy</a>