Pippas Story

Published February 23, 2024 tag category
Pippas Story

*** A Story Of Feminisation.

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls.

Reflected before me was a sexy, if a little sluttish looking woman in her thirties. The only discrepancy being that I was actually a 37-year-old man, happily married and, here at the precise instruction of the woman I loved and was married to.

She had returned home a day early, from a trip to her sisters place, in the country. What she found as she walked in, was her husband wearing her underwear and, fully made up to boot. She insisted that, if I wanted to remain married to her, I would agree to dress up for her, whenever and wherever she instructed me to. I was flabbergasted and truly lost for words. I didnt want to lose her but I knew she could be a vindictive cow, when she wanted.

I agreed meekly to this arrangement, which is why I am here, about to enter a transvestite club on the Earls Court Road, fully transformed into my female persona, Pippa. In my hand I hold a sheet of paper and, have instructions that I must show it to anyone that I speak to, once inside the club.The paper reads as follows:
I have been instructed to show this to anyone I talk to.

Please read it thoroughly. Please note that the woman you are talking to is actually my husband. He is known as Pippa when dressed like this. I have asked him to fulfill a mission for me. It is in four parts, the first of which he/she completed by entering the club. She cannot disclose her mission parts until they have been accomplished but, if asked about it once she has completed them, she must answer all questions fully and truthfully. Barring her identity, Pippa must reply honestly to any question she is posed and has been asked to be reasonably accommodating to peoples requests of her. She is not to be harmed or marked in any way. Have fun!

I paid and went downstairs to the bar and dance floor. The barman wasnt busy so I went to order a drink, as he approached I realised I was going to have to speak to him. I nearly lost my bottle but he was already asking me!
As humiliated as I felt, I handed him the piece of paper and watched blushingly as he read it all. His smile grew as he read through the wording and, handing it back he asked what I wanted to drink. I ordered wine and handed him the money. He disappeared to the far end of the bar and, I saw him talking animatedly with a small group of very convincing cross dressers.

He pointed right at me and 2 of the girls walked right over to me and, striking up conversation immediately. I handed them the paper and grew nervous at what might happen. One of them confirmed that this was true with me, asking me if it were a wind up. I reassured them of its validity and that I was a willing participant in this whole affair. One of the two whisked away my instruction sheet and took it over to the rest of the group where, she passed it round to them all. I saw each of them read through it, occasionally glancing over to look lecherously at me. The one that had stayed with me leant forward and planted a quick kiss on my lips, her tongue licking mine briefly.

She held me by the forearm gently stroking my silk gloves as she said, "I think its time that you met the rest of us Pippa, because I get the feeling were all going to get to know you pretty well tonight." She smiled knowingly as she looked me straight in the eyes.
I was wearing some seriously classy clothes that really gave me the look of a high-class hooker. Long shiny red silk gloves, a thin red suede choker around my neck and a black and orange snakeskin three quarter length PVC coat were the items that framed my torso. Underneath I wore a see through red blouse with a thigh length patent black /skirt/leather-skirt/">leather skirt, concealing a blood red suede Basque which had been fitted especially with a patent leather waist reducing corset and that snapped shut using a thick flap that was made as a harness that firmly held my manhood in place, hidden away between my legs.

My wife had fully depilated my body, leaving me as smooth as a babys bottom from head to toe and, had insisted on buying me a pair of silicon falsies which were now stuck on my hairless chest, giving the impression that I had /real/real-boobs/">real boobs which were held tightly in place by the Basques three quarter cups. She had also made sure that the waist-reducing corset was as tight as possible before Id left the house, pulling my waist in from a chubby 36" to a much more appealing and feminine 26".
Over the bottom flap, I was wearing a pair of lacy tanga knickers and, covering my legs was a pair of red silk hold-up stockings with a Cuban heel and lacy patterned top. My footwear consisted of a pair of leather boots, which came to just above my knees and sported a fairly thin 4" heel, making it difficult though not impossible for me to keep my balance and walk with a fairly feminine gait.

My eyebrows had been plucked and shaped and my wife had made me up very convincingly, spending a lot of time on my eyes, making them very bold and eye-catching. My lips also were full and glossy, in a bright red contoured with a dark lip pencil. To top it all off, my wife had insisted I wear a bright red short wig, styled into a modern cut that was swept forward over my ears and part of my cheeks.

Although they could not be seen whilst I was dressed, my /mistress/">mistress had also given me a pedicure including painting my nails scarlet and, had stuck false nails to my hands with superglue, making sure that I had no hope of removing them, they too were painted in the same vivacious scarlet polish.

The corset made me stand very straight, pushing out my chest and bum and accentuating my curves, while the fairly thin heels on my boots meant that I had to be very careful of my balance while I walked, making me sway my hips a little in a very sexy and enticing manner. As we walked toward the rest of the group, we stopped to put my coat away and get a ticket in return, leaving my upper body showing the sexy Basque and corset through the sheer material of my blouse.

As we got closer I realised that not all of the group were crossdressers and that 2 of the party were stunningly attractive young women. Myself included there were 6 of us in all and each member of this little gathering had a big wide smile plastered over his or her face, all that is except for me.

I had begun to dread the situation and all the while grow excited at the prospect of the evening to come.The group consisted of a married couple Melanie and Alphonse, better known as Alison in his TV state and, a threesome made up of a very stern but beautiful looking woman in her thirties together with the two girls that had made the initial contact with me. Both of these were transsexuals, one pre-op TS the other a fully transformed post-op TS. All appeared to be very sexy and feminine women, with the exception of Stefanie the pre-op TS who looked exactly like a model but, was sporting a semi-erect penis that was strapped in a leather harness, clearly visible in shape through the Lycra skirt she was wearing.

Davinia, the post-op TS was the first to begin the introductions explaining her TS status and nodding to Stefie who, in turn explained she was a TS and that she and Davinia were here as a trio with their Mistress Marikka. The imposing figure of Marikka immediately approached me, looking me up and down appraisingly as she did so. She stopped only inches from my face and starring me right in the eyes, she said: "Nice to meet you, Pippa. You have attained a suitable standard. Youre Mistress must be very pleased with you. Will you agree to becoming my third /submissive/">submissive for this evening, in the absence of your true Mistress and, abiding fully by her prior instructions of course?" Stunned and surprised by this unexpected turn of events, I found myself agreeing to do so without truly thinking through the implications of my actions. "/good/good-girl/">good girl." Was all that she replied.

Before I could think Alphonse was introducing himself, as Alison of course. She explained that she was here with her wife Melanie and, that they said that they were sisters when he was dressed in public. He also explained that it would be his/her 21st birthday at precisely three minutes past midnight, which was why the group were out celebrating together. "I hope that my joining you will be able to make it a more memorable experience still." I blurted out nervously. "Oh, it will believe me!" exclaimed Melanie, as she leant over to make the final introduction.

They all grinned as they turned their looks upon me. We chatted for a while and drank a good few cocktails, as the group made me feel more comfortable and, less resilient! Melanie came up with the idea that as we were her playthings this evening, we should be entertaining her, requesting that we three dance a while. "I dont think I can dance in these heels." I said without thinking. Marikka looked over at me and replied: "Youd better learn then and quickly, because it wasnt a suggestion!"

I realised that Id just been issued with my first command and, tottered over to the dance floor, the 2 girls egging me along the way. It took a few minutes for me to get my balance but as the beat started to fill me I got bolder and bolder. I realised that I was being sandwiched by the girls, Davinia in front of me and Stefie behind, every so often allowing her strapped in cock to brush up against my backside. As the sandwich got tighter I felt Dees boobs brushing up against me and, pushing me back into Stefs ever-growing member.

They started running their hands all over me until Dee grabbed my face and kissed me deeply. As she did this, Stef was rolling my skirt up over my waist, which allowed his dick to poke my arse through the strap of my Basque. What horrified me was that I was becoming excited at how publicly I was doing all this and, I could feel my own cock growing ever bigger, pushing backward against the Basques strap stretching toward my own arsehole.The set finished and we headed back toward the group, neither girl allowing me to lower my skirt and adjust myself.

Marikka instantly noticed and ordered me out of my skirt. I was told to put it in my handbag and continue the rest of the party without. I blushed under the make-up but did as Id been instructed. The bulge under my legs was obvious and Melanie decided it was time to join in. she hiked her skirt up revealing her bare pussy and, leaning onto a bar stool told Alison to start eating! Ali got to her knees and began licking with all her might, juicing Mel right up.

I was very pleased that the spotlight had fallen away from me and onto the horny couple. We watched as Ali brought his sister off with her tongue, Mel indian santali xvideo came ferociously gushing her sticky juice all over Alis face. She looked down at him and smiled.

"That deserves a return of favour little sister, get up and remove your panties my love." Ali did so immediately, freeing her rampant throbbing 8" hard-on, which sprang forward thrusting out in front of his body. "Lean back against the stool as I did when you ate me Darling." Ali was ecstatic at the thought of his wifes lips around his knob but was surprised when Mel ordered Pippa to her knees in front of his cock. "Your turn Pippa, eat up and eat it all now, you hear?" Marikka pushing the hollow of my back, propelling me in the right direction and making me almost fall to my knees.

I had never given head to a man before and, this little stallion was as hard as rock and twitching in my face. I began by licking the balls and worked my way up the thin long shaft, to the bulbous /circumcised/">circumcised head at the tip. The stem was pulsating making the head throb almost to bursting. I grabbed all of my courage and wrapped my lips around it, sucking and licking as I descended the first 6" of this bulging mass of meat. I began pumping up and down the stem until finally I managed to open my throat and take him/her in fully. As I did this I felt a gush of sticky goo pump into my throat. I almost gagged but tried aimlessly to drink it all down, I would have too had he not pulled out and spunked over my blouse.

I stood immediately she had finished cumming and, stated to the group that I had just achieved the second part of my mission. I had been instructed to have at least one cock spunk into my mouth and, I was to drink as much spunk as was possible this evening. Marikka smiled leeringly at me and nodded to herself satisfyingly.

The blouse joined my skirt making my bag bulge awkwardly. It also left me in only my underwear and publicly to boot. Marikka immediately decided that once was not enough and made me repeat my performance with both Stef and, more embarrassingly with the barman, openly behind the bar, so that anyone who wanted a drink could see what was happening. So I was currently in my undies, dressed as a woman with my /cock/cock-hard/">cock hard as rock but held in between my alain lyle porn legs and, I had just drunk the semen of three men that Id only just met!
What I wondered could possibly happen next? No sooner had the thought crossed my mind that, I heard Mel exclaim loudly: "Alison wants to taste Pippas clitoris girls! And since her birthday is rapidly approaching, I think she should have her wish. Any objections ladies?" Marikka gave it her full approval and ordered me to lose the panties. Once they were off I felt her hand as it unclipped my Basque and, released my still throbbing manhood from its satin prison. I opened my legs a little and allowed it to stand proudly to its full 7" capacity.

Marikka ordered Stef and Dee to prepare me and, they started kissing my face, lips and neck intensifying my excitement and making my dick throb wickedly. My bum found the stool and I leant back as I allowed my first man to give me head. Ali was an expert; she drove me wild as she bucked her head up and down my pole. As I began to scream I felt someone push my panties into my mouth, quietening me so as not to become a nuisance to the club. I came in buckets but Ali somehow managed to drink it all in, then she stood up and kissed me letting a mouthful of my own cum run down my throat.

I again exposed that the third instruction of my mission was complete. To be blown by at least one other partner, preferably a man. Stef managed very quickly to get me hard again as Marikka ordered me to fuck Dee and to cum in her TS pussy. It took me a lot longer to cum this time and, it caught me by /surprise/">surprise happening as it did when I felt Stefs dick pushing its way into my arse. This was it, the final part of my mission! I couldnt hold back as I felt the pressure building me to a shattering climax, deep in Dees tight hugging pussy. A moment later I felt warm and sticky inside, as Stef followed suit.

We were all practically worn out as a cheer went up to celebrate Alis birthday. We drank some more and I explained to the group that my mission was complete and, following strict instructions, I must now return to my wife and graphically describe my evening while she tried to coax another /erection/">erection out of me. I quickly retrieved my PVC coat and put it over my underwear, having first positioned my bits back into the Basque.

I was heady with all that had happened to me, yet I felt fulfilled at the fact that I had completed my mission in its entirety. My wife and Mistress greeted me eagerly as I returned home, quickly guiding me into the bedroom, but thats another story...