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Teresa, Trish, Nan and Guests
I met Nan on a subscription alternative dating site. Her posts and private messages blatantly communicated she was into dominating men and women but also into transformations. I had been crossdressing in private, sexual settings for a few years which often involved strap-on play but never with a man. In fact, I had never even performed oral sex on a man but was really curious – I just wasn’t sure how to go about it or if I was truly ready.
After only a few private messages about how I would love to be dressed as a woman under her guidance and engage in some play/exploration, we decided to meet the coming Saturday. She told me to get a full body wax the day before.
Nan told me to meet her at a restaurant so we could spend some time together in a neutral location before moving to the next step. She was dressed in jeans and a t-shirt and tasteful heels. Lunch was slightly awkward but anticipatory. As we completed the meal, she said it was clear we had chemistry and that I could just follow her to her house, a 10 minute drive.
After we arrived, she showed me the house including her upstairs which has a master bedroom, two converted bedrooms, one with endless clothes, shoes dressers and a dressing vanity and sink with small shelves of makeup. The other converted bedroom was a play room with blacked out windows decorated primarily in red and black and featured a leather couch in the middle, an elevated, throne-like chair, ceiling hooks, a long counter with toys and restraints of every type.
She then showed me the basement containing an entertainment room that would hold 30 people with a long bar, a large bedroom and a bathroom. Clearly this woman entertains people and has a very interesting life.
Nan then led me the kitchen on the first floor of the house which had a desk and computer where we sat down and looked through images of her dressed in different bondage clothing with men and women in her play room. I saw images of her pegging men, women and crossdressers.
Nan asked me if I wanted to engage in some role play with her involving submission and strap-on play or if I was willing and interested in taking things to something of an extreme? I had to think about it for a minute – I had been fucked numerous times by a strap on so I wasn’t sure what she had in mind so I started asking questions to which she said I had a choice. If wanted to really surrender, I could not ask questions as she would be making all the decisions. I decided to risk it and hope things would be fun but safe. Nan pulled out her phone and began texting with for reasons unknown to me.
She led me to a bathroom next to the play room upstairs and told me to strip down after which she inspected the wax job and remarked it was perfect. Nan left me alone in the bathroom and told me to give myself two enemas with the supplied materials on the bathroom counter. When I was done, I should put on the black silk robe and meet her in the play room.
Nan was now wearing a mesh halter top that showed her tummy, short dark blue skirt, panty hose and black heels. She had also applied a lot more makeup with including shiny black lipstick. She looked stunning.
Before getting dressed, Nan said it was important to take things gradually so she told me to bend over the vanity chair so she could squirt in some lube and then a medium sized plug to stretch me out. Medium to her is what I considered large and it was painful going in but the pressure, once inserted, felt great.
Nan then guided me to sit at the vanity so we could talk about clothes, jewelry and start the makeover.
Nan first applied a primer so the makeup would wear more evenly followed by some concealer under my eyes. Since my skin can be on the oily side, Nan used a matte foundation and then added blush to my cheeks. I have big eyebrows but she filled them in a little with a pencil and had me close my eyes while she went to work on the eye shadow. A bit of waterproof eyeliner and mascara really removed any hint of maleness; I could not believe what I was seeing in the mirror. Nan used a red lip liner before painting my lips with a bright red shade that had endless shimmer.
Nan had laid out a few wigs and decided on a medium length brunette version which she attached firmly. Still wearing only the silk robe, my erection was at 100% and seemed to be distracting her but she didn’t mention it.
Nan gave me a choice of earrings in a box on the vanity and I chose some sexy but smallish clip-on hoops. We finished the jewelry with a pearl necklace.
By this time, I had such a hard erection that Nan said it would be an issue with the clothing and pictures we might take so she handed me a pink condom and had me bend over the back of the couch. She donned a pair of black gloves, removed the anal plug and told me to jerk off while she fingered my stretched and very slippery ass. It took about 30 seconds before I came in the condom at which point Nan stopped fingering me. I thought for sure she would make me eat the cum from the condom but, instead, she put the anal plug back illegal bahis into my ass.
We walked into the large closet where seemingly endless choices awaited. Nan liked the idea of red for today so she selected a gorgeous pair of shiny red panties (not a thong), matching bra and black thigh highs with red lace. She helped me into them and adjusted everything before handing me a stretchy red, hip hugging dress. It took a little effort to make it look good but felt so sexy. Next she handed me a pair of red strappy sandals with a three inch heel. I sat on a small bench to put them on. I have worn heels this size many times so I had no issues balancing.
At this point, I thought the transformation was complete but Nan had also picked out some red elbow length gloves to add even more femininity. She said my nails weren’t long enough to be sexy so she would just conceal them.
Finally, Nan handed me a red purse which really completed the look and told me that, for tonight, my name was Trish.
We returned to the vanity where Nan looked through some drawers for purse items. She gave me some touch-up makeup, a condom, a tampon, lube, a small case with four cigarettes and a small lighter. She then gave me some perfume to apply and then put in the purse. Nan had me bend over once more so she could remove the anal plug which she then made me lick clean before placing it in a small sink.
Nan wanted to get pictures so we walked around her house where I posed in different vanilla positions. She said she was really happy with the way I looked and that any man or woman would be eager to spend a night with me.
As we wrapped up shooting pictures in her living room, she led me downstairs into her basement which had a large entertainment room, full bar, big TV, bathroom and a bedroom. I sat at the bar as Nan made us a few drinks and then the doorbell rang. Nan went upstairs but said she would be right back.
Following Nan was was a gorgeous blonde wearing a white dress and white heels with impeccable make-up and hair. Nan introduced the person as Teresa and told her to sit next to me at the bar. Teresa told me Nan taught her how to crossdress about a year ago and that she was a frequent guest here. I now knew at least part of what Nan had planned for me tonight and my adrenaline skyrocketed.
As the three of us talked and drank, Teresa opened her purse and lit a cigarette in the hottest way imaginable blowing smoke upwards. She asked if I wanted one but I said not right now. Teresa complimented me on my clothes and makeup and said we should dance. Nan, still behind the bar, put on some music while Teresa took me by the hand to the open area of the room. After a few songs, we sat down on one of the couches. Teresa lit another cigarette and, after a few puffs, leaned over and kissed me with a full mouth of smoke. We made out for a few minutes, kissing and biting each other’s neck and feeling each other all over until Teresa dropped to her knees, pulled my cock from my red panties and started taking me in.
The sensation of her soft lipstick covered lips and wet mouth was overwhelming as she seemed to take me deeper and deeper. After only a few minutes, I couldn’t resist and started cumming hard! Once she had sucked the last drop of my cum, Teresa slowly moved up toward me and started making out with me sharing the cream that I had created. We kept making out, swirling my cum between our tongues for what seemed like forever until we both noticed Nan was taking pictures of us.
Teresa, Nan and I went back to the bar where the two of them shared another cigarette and we all finished our cocktails. Nan said we both needed to touch up our makeup and that Teresa could help me so we grabbed our purses and went into the large, marble bathroom. We both peed sitting down and then Teresa touched up my face and reapplied lipstick to hers. Teresa asked me if I had ever worn a tampon to which I replied I had not but was willing to try anything tonight. I opened my purse handing the tampon to Teresa for guidance. She had me spread my legs with hands on the counter and fingered me for a while, which gave me another erection, then used the applicator to insert it and finally gave the little string a tug which felt great. She then kissed me and said we should go back out to the bar.
Nan said she thought the two of us girls were being naughty in the bathroom and that we needed to remember who was in charge so she had us stand in the middle of the room embracing one another. From behind the bar, she pulled out a small but mean looking paddle which she then began using on our dress covered asses. As each paddling seemed to increase in intensity, Nan ordered us to make out, pulled up both of our dresses and spanked us so hard — red marks were everywhere. If we stopped kissing to catch our breaths, Nan would strike us harder. Just as I thought I could not take any more, Nan stopped but said she was glad to see I was wearing a tampon.
The evening was, so far, the most erotic night of my life but I knew Nan had more in store for me and for bedava bonus veren siteler Teresa. As we were sipping a third cocktail and nursing our sore asses, Nan said two of her male friends were on their way over and that we would be their lovers for the night. I gulped knowing I was definitely going to lose my virginity tonight and wondered if I had gotten myself in too deep but also knew there was no going back now. Teresa, taking a drag on a cigarette, said she had lost her virginity in this house about a year ago and it was okay to be nervous. She kissed me again and put her hand on my knee.
Nan said we had a few minutes to change into some lingerie and prepare, as women, for the night so we headed upstairs to Nan’s closet. I was given a red and black basque with garters, black thigh highs, a pair of black lacy panties and a transparent gown with a pink bow on the back. For shoes, Nan handed me a pair of 3” black heels with a clear plastic toe. I stripped out of my dress and underwear and put on the lingerie. It was extremely feminine looking as I peered into the full length mirror.
Teresa was changing into a pink corset with garters that attached to white fishnets and 5” white, open toe heels. I was in awe that she could walk in those heels but she made it work.
Nan was so impressed by our looks, she took some pictures of Teresa and I holding hands, kissing and hugging.
As we continued to bask in our lingerie, Nan headed back downstairs and told us to visit the bathroom because it would be our last chance for a while. Teresa closed the bathroom door and had me bend over again to remove the tampon I was so much enjoying in my pussy and I suddenly felt her tongue rimming my horny hole which made me go nearly numb. At her urging, we switched places and I essentially fucked her hole with my tongue, going in as deep as I could tasting her ass. She warned me she might cum if I kept going and that we had “dates” downstairs so I stopped and we came to our senses.
Nan had left us different lubes with a rubber needle application bulb which we both used on each other. Teresa said the guys we were going to meet had de-flowered a few crossdressers and that there was nothing to worry about.
As we headed back to the basement holding hands with our heels clicking on the wood floors, we entered the entertainment room and met the guys names Deck and Russ. I was incredibly nervous but also eager. The boys pulled out bar stools for us and lit Teresa’s cigarette while we drank some shots that Nan had laid out. The alcohol was kicking in because my nervousness was fading and I was getting really horny. Teresa told me it was time for me to smoke a cigarette so I opened my purse and took one from the silver case. Deck immediately lit the cigarette for me and I tried to make it look as sexy as Teresa did.
The boys asked us to dance so I took Deck’s hand and we slow danced one tune sort of vanilla like but during the second song, Deck’s hands were all over me. When the song stopped, Deck romantically kissed me. My mind and body were whirling to the say the least. I felt completely feminine as I reached down and rubbed his crotch through his jeans. After a few minutes, Nan directed us into the bedroom.
The bedroom right off the entertainment room was big with a love seat and a comfy chair surrounding the bed. The room was lowly lit but had a huge bed with dark purple satin sheets and fluffy pillows. On both nightstands were condoms, lube, nipple clamps, dildos and a few popper bottles. As we flowed into the room, Nan told the boys to sit in the love seat and for us girls to get on the bed and start making out. It did didn’t take long before I was caressing Teresa’s cock and and she was fingering me again. I noticed the boys were stripping down and stroking their cocks. I couldn’t believe I was fooling around with another crossdresser in front of two naked men but I was in for the duration.
Deck stood up and helped me off the bed and onto me knees where I was, for the first time, inches away from a hard cock that I was about to suck. I started by massaging it but could not help myself and kissed the tip of his cock. I gave it a few more smooches before taking as much of it as I could into my lipstick covered lips. I had throated strap-ons so I soon got the hang of it and was able to take it into my throat and cup his balls. He seemed to have a lot of staying power so I really took my time and enjoyed the new sensation. Out of one eye, I could see Teresa doing the same to Russ but with more savviness.
I could tell Deck was close to cumming so he pulled me up and had me lay down on the bed. As he joined me, he opened my legs and pushed them back and kissed me deeply. I felt a finger enter me and then two and then three as Deck prepared me for a life changing experience. He made me lick his fingers when he thought I was ready, kissed me and slowly pressed the tip of his warm, hard cock against my well-lubed anus. I put my arms on his ass cheeks as he continued to enter me until he was yatırımsız deneme bonusu fully inside. Painful as it was, I knew it was right as Deck slowly started sliding in and out of me. I was in heaven as he started sawing into me while kissing me and biting my nipples through my basque. I had never felt like this before; a handsome man’s cock inside me and kissing my lipstick painted lips with my heels in the air. I wanted it to never end.
Teresa was laying prone beside me being fucked from the side as she reached over and started kissing me which didn’t last long because Deck turned me around so I was on my knees. I asked him if I should remove my panties but he said he liked pulling them to the side. As Deck entered me again, it was completely different because he was firmly holding onto my hips and pounding his cock harder and deeper than before. I was losing control and sort of fell into a daze – I don’t know how long he was fucking me this way but I had no way of caring by the point. Finally, Deck pulled out, slapped my ass REALLY hard and called me a whore.
Before I could even catch my breath, I noticed Russ pulling out of Teresa and pouring lube onto his dick before ramming his cock, which was bigger than Deck’s, into me, going really deep and causing a pain I had never felt with any strap-on, even a big one.
I noticed Teresa was now sitting down on the love seat smoking a cigarette as Deck got in front of me, slapped my face and said, “Bitch, take my cock now!” I opened wide and sucked him as much as I could even though I could hardly concentrate on anything with this big cock hammering in and out of my pussy.
So, there I was, fully transformed into a woman wearing lingerie and heels being fucked in both ends with an audience.
Russ was breathing really hard and I was totally cum drunk by this time so I couldn’t keep Deck’s cock in my mouth. Russ started cumming, I could feel his cock twitching and his warm cum in my bowels. It was THE most erotic moment of my life. I was completely spent by now as Russ slowly pulled out and moved off the bed sitting down next to Teresa. Deck laid down on the bed and ordered me to mount him so he could also leave his seed inside me. Deck’s cock slid easily into my hole after the stretching and violent fucking by Russ not to mention it was slippery from all the lube and Russ’s jiz.
Deck pounded me while holding me up by my under arms. He was slamming into me, my butt cheeks slapping his balls, and came in just a few minutes after which he tossed me aside and got off the bed.
I was now alone on the bed with my make-up a total mess and my ass stretched wide from being fucked by two guys for what must have been 45 minutes. Teresa came over and embraced me with a kiss. Deck and Russ both said that was one of the best fucks ever and that we should have some drinks. Nan said not yet and ordered Teresa to lay on her back and for me to squat above her. My legs were like noodles but the boys helped me balance above her face. With Nan’s insistent direction, I was able to push out most of Russ and Deck’s cum which dripped into Teresa’s mouth. I rolled off her and collapsed. Teresa sat up, lit a cigarette and let the cum and juices from my ass slowly drip down from her mouth and onto her chest as Nan took more pictures.
The boys and Nan left the room, used the bathroom and congregated back at the bar. Teresa kissed me with her cum covered lips and shared her cigarette with me. We needed put ourselves back together so we walked to the upstairs bathroom. I told Teresa that was the most intense thing I had ever done but that I had no regrets. When we looked in the mirror, we appeared like street hardened hookers. My makeup had run all over my face and my lingerie was soaked. Teresa must have engaged in some very deep throating or gagging as her eye makeup was a disaster.
We stripped down, put on robes and reapplied our makeup leaving us looking really good again. Nan had laid out some simple clothes for us to wear. For me, another pair of red panties, a red silk chemise and some sexy slippers with a good heel. Teresa put on the same outfit but in black.
When we entered the basement room, the boys and Nan were in the bedroom with the door closed but we could hear a lot of noise so they must be having a good time.
Teresa and I sat at the bar, I was really sore, had another cocktail and some cigarettes. Nan and the boys finally walked out of the bedroom completely naked, clutching their clothes and left the basement.
Teresa and I had been drinking and smoking for a while when she remarked that she got fucked hard by Russ but that he had not cum in her and wondered if I was up to fucking her and filling her with spunk. I was getting really tired and wasn’t sure I could perform but Teresa was pushy so we had an energy drink and headed back to the bedroom.
The sheets were nasty so we quickly changed them and laid down on the bed kissing and softly touching one another. I was on top of her and had fingered her to a near orgasm before very slowly putting my cock inside her. We must have made love for over an hour, alternating between positions and who-fucked-who before I finally filled her with cum with my tongue in her mouth and her gorgeous legs pinned back. We stayed in this position for a while kissing and caressing each other untilI we fell asleep.
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