Of Course The Offer Still Stands

She had a point. Putting a single dick in my mouth had turned my life upside down, yet when presented with the next opportunity, it didn't feel right. Maybe I was a hopeless basket case.

"The effort?" I asked.

"Yes, to be a true sissy princess takes some serious effort. I know a very interesting couple at one of the clubs that might like you, but they're very selective. I think you could get their interest, but you're going to have to work at it to close the deal."

I was intrigued and agreed a female in the equation might be what I was looking for, yes. So many cross dressers were looking for that very thing. My physical condition, style and deportment, skin care, etc., needed a lot of work, but I was on that path since I had re-located anyway.

We ended the evening on that note. I showered and washed the make-up off, returned everything, including the eye lashes and as I left we hugged as two people that had shared something together hugged. I was entirely satisfied, In spite of the lack of sexual satisfaction.

"I'll send you the pictures," Ms. Sheri said as I departed. "Of course the offer still stands, if you're willing to put in the work."

Ms. Sheri emailed me the photos and I loved them. I vowed to myself that I would put in the effort to be that princess, to the extent I was capable, and see where it led me.

I bought Kevyn Aucoin's 'Art of Make-up'. I took up jogging again and changed my diet. Went through extremes to practice good skin care. I ended up losing 18 pounds as Ms. Sheri and I kept in touch over the next several weeks. I spent hours in the highest heels I could find at the thrift stores, building up my calves. The loss of weight and practice were paying off and heels were becoming almost comfortable. There were many other things involved and the only issue I ran into was a female co-worker examining my thinned eye brows. I caught her studying them on more than one occasion. I think she was on to me as she commented that I smelled nice one day as well. My male clothing had started to become very loose on me as well and I had to buy a few new male clothes.

Ms. Sheri monitored my progress and eventually confirmed a date for us to go out to a club. It was to be a Saturday and we would get ready together at her home. I had found a short A-Line dress with elbow length sleeves in baby blue that Ms. Sheri approved of. It had a sexy skirt that would allow quick access underneath and lacing on the chest in order to encase my fake breasts. I felt so feminine whenever I wore it as it displayed my new silicone breasts prominently and the flared skirt gave the appearance that I had hips. I wore a over bust long line corset in pale pink satin underneath.

She also advised that I visit a clinic for a STD screening. A clean bill of health would be helpful in ensuring I wasn't a clandestine glory hole slut.

Ms. Sheri had also put me in touch with a salon that specialized in a transgender clientele for a waxing the Wednesday prior. I'll skip the details, but I emerged hairless, everywhere, and was feeling good once again by Saturday. It had become quite a process to be feminine. I hoped it would be worth it in achieving my ultimate goal.

Ms. Sheri supplied the wig for the evening. Otherwise, my wardrobe was now mine. I prepared in advance with an enema, and other prerequisites and arrived at Ms. Sheri's around the dinner hour. I had done my nails to match the dress and shoes and wore driving gloves for the trip. After a couple of hours of preparation and a bite to eat, she provided me with directions and we drove separately, just in case.

I had ventured out dressed after dark a few times at this point, so this wasn't the first, but my legs sticking out from under the short skirt of the dress while wearing 4" heels was definitely a first. I felt so exposed and vulnerable. I wore a short women's jacket and carried a small purse along with the overnight bag I had used for my things. I considered how females definitely had the advantage in this regard as they'd experienced this their entire lives. My clean shaven cock and balls went into hiding when the cold air hit the exposed skin between my thighs and padded bum booster panties I wore. I thought I must look sexy and fuckable to anyone that observed me. Ms. Sheri said I would definitely pass in the darkness and was happy to be my escort.

I felt horribly self conscious and poorly dressed as soon as we met up and entered the club. It was a mixed crowd of gay men mostly and only a few dressed in female attire. Ms. Sheri greeted the many patrons that she knew and called me her latest project when anyone asked who the new girl was. I tried to be sociable, but I was freaking out on the inside. I didn't see anyone matching a male and female couple as we made our way to an empty table.

We had just started on drinks when I noticed them making their way towards us. Lisa, I would soon learn, was dressed for a stage performance. He was heavily made up and sparkled all over in a shiny form fitting dress. He wore absolutely beautiful floral pattern stilettos and had a high stacked head of blonde curls.

His female companion was also blonde and her protuberant pair of tits half came into view as she removed her coat. Her breasts were nearly falling out of the confines of a tight leather top she wore; the outline of what appeared to be succulent nipples visible through the thin leather. She was very curvy otherwise and by all appearances, a genetic female. She had wonderfully full lips that caused one's mind to wander to thoughts of a woman's puffy labia, begging to be spread open to find the treasures within. She had nice blue gray eyes as well.

They were indeed an idiosyncratic couple.

Ms. Sheri introduced me to Chrystal, the female of the pair, and Lisa, her male companion.

"You weren't kidding, Sheri. She's a cutie," Chrystal said as she gave me the once over. "I just love your make-up," she said, as she looked me in the eye.

"Thank you," was all I managed to reply meekly as the conversation moved on quickly.

"Good crowd tonight, isn't it, Lisa. I hope you brought your 'A' game.", Chrystal said to Lisa as she surveyed the room.

The waitstaff brought them their order and we chatted. They wanted to know where I came from, how I met Sheri, they were shocked I'd never been in a gay bar before, then not, considering my choice in clothing. How I'd look lovely at a Spring wedding though, etc..

I had been setup with my choice of dress by Ms. Sheri, but I held no malice towards her.

The DJ announced fifteen minutes until the drag show and Lisa grabbed me by the hand and said "Come with me backstage. We can pee in the stage bathroom."

We waited our turn with the few other performers for our turn in the small bathroom. Once inside Lisa whipped out a pick me up and offered me a hit. I obliged her, hoping it would calm my nerves. She chatted as if we were old friends.

She put her hand on my waist in the close quarters and felt my corset. "Oh, I see you and Sheri share similar taste in clothing. Let me see, Doll."

I raised the skirt of my dress to expose myself and she said "Very nice," as she ran her hand over my corset and around to my ass. "You cheater," she exclaimed as she felt my padded ass. It was all very exciting and I could have had sex with her then and there in that cramped bathroom, but the knocking at the door wasn't going to permit that.

"Well, it's time for the show. I'm so glad you came. You better get back to the table," and she kissed me on the cheek as we exited the bathroom. We weren't there to pee, I realized.

It felt like every eye in the place was on me as I made my way back to the table. Note to self, short, baby blue dresses are not evening gay bar attire. When I landed back at our booth Ms. Sheri handed me a compact and tissue, saying "You messed your make-up, Dear." Lisa had left a very noticeable lipstick print on my cheek. It didn't go unnoticed by Chrystal. She smiled.

We watched the show, lasting just a half hour or so, and I relaxed as the buzz worked it's way through me and I didn't have to interact very much. Lisa did a reasonably good job with a Cher song, but a Liza look a like received a wild response for an over the top "Maybe This Time". Liza was awarded the trophy that appeared to be recycled for every show.

The DJ fired up the music and it was difficult to converse over it. After we shared another round of drinks and Chrystal and Lisa danced a bit, Lisa whispered in my ear "Would you like to take the party to our place?"

I nodded my reply. I couldn't wait to get out of there actually. Ms. Sheri passed on the invitation they extended to her, so it would be just the three of us.

I followed their Mercedes closely in my own car. They drove cautiously as we had all been drinking and were all probably perilously close to the legal limit at this point, if not a smidgen past it. We arrived at a very large home in a wealthy part of town. I'd guessed it was a 5,000 sq. ft. home. Someone had some money from some where. I parked in the guest parking spot off of to the side of the three car garage.

We entered through the garage entrance to a truly impressive home. They gave me a quick tour as we made our way to the basement. I had to take my shoes off to navigate the stairs. The stairway led to a large entertainment room, with bar and seating, a very large television and billiard table. It was all tastefully done.

I had to pee badly at this point and Lisa showed me to the basement bathroom. It was like a high end Vegas Penthouse bathroom, bigger than my living room probably, with a three-headed glass enclosed shower and accent lighting. Needless to say, I was impressed.

When I returned the lights were low and music was playing. Chrystal and Lisa were busy making Margaritas at the bar. They poured tequila shots as well, for good measure. It was apparent I wouldn't be driving again anytime soon.

We chatted about this and that and the conversation turned to Sheri and I's interest in corsetry. Lisa said to Chrystal that she just had to see what I was wearing and had me stand and raise my dress.

"Higher, a little higher, more," Lisa kept saying as she laughed. I kept going in the intoxicated spirit of things until I had raised it over my head. That's when I felt his hands on my waist. When I lowered the dress below my chin, Lisa planted her lips onto mine and immediately started to probe me with the tip of her tongue. Our lip stick coated lips melted together and it felt fantastically good as our tongues danced with one another. It had been years since I'd kissed like that.

I felt Chrystal pulling on the rear zipper of my dress as Lisa kissed me. My heart raced and my cock strained in my panties as they slid the dress off of me. It was all done at a slow pace as Lisa released me and they pulled the dress off of my shoulders and down my legs. They slowly explored me with their hands as the dress fell to the floor. They were truly a unique couple. It was the most sensual I'd felt in all my life I think as I felt Chrystal's large breasts pressing against my back as they sandwiched me between them. I could smell Lisa and my own perfume and make-up over the tequila and saliva we shared. I may never forget that mix of aroma's.

Lisa resumed kissing me as Chrystal explored my padded ass and thighs. She reached around with both hands and explored the front of my panties as she nuzzled my wig away and kissed my neck. I was stimulated everywhere and I pulled Lisa tightly to me and grasped the cheeks of his ass, trapping Chrystal's hands between us.

Chrystal worked her hands into my panties, pulling my trapped cock free of the crotch of the panties. My cock came to full erection almost immediately. She explored my five and a half inches as she worked her way up. Chrystal then nibbled at my ear. I jerked at the sensation and Lisa and I broke off our kiss.

Lisa stepped back and looked down to see Chrystal's hand stroking my hardness through the front of my panties. He turned his back to me, inviting me to unzip his own dress and I obliged him. A beautiful bra and tremendous pantyhose covered butt came into view as he lowered his dress and stepped out of it. He wore a thong and my gaze fixated on his nylon covered cheeks. I reached out and caressed them. They felt as firm and smooth as they looked. He stood there in his heels and pushed his ass out to me, letting my hands linger on him. My cock couldn't become any harder as Chrystal's hands continued feeling me as I let my own hands wander up Lisa's lean back.

Lisa turned towards me and reaching into his hose and thong, bringing his restricted cock into a vertical position. He had a cute circumcised penis, much like my own I thought. I reached out and rubbed it with my palm, then gently squeezed the head through the layers of nylon covering it.

I felt Chrystal find the knot of my corset laces and begin to untie me as she likely watched me explore her husbands cock. I realized this and stopped what I had been doing. Lisa removed my silicone forms as the corset loosened and found my excited nipples with his finger tips. I had been using suction devices on myself for a while now and my nipples had become extremely sensitive. I began to leak pre-cum at his touch. My corset now loose enough, Lisa undid the front clasps and they removed it from my now bare torso. Chrystal ran her hands up my rib cage and copying Lisa, found my nipples and pinched them rather firmly. My balls tightened in my panties and I felt my cock pulse.

I turned away from her to avoid any premature releases and Lisa and I turned our attention to Chrystal. To Chrystal's breasts to be more accurate. Lisa unbuttoned her leather halter to reveal a magnificent pair of tits.

She wore a sheer underwire bra which only served to enhance the appearance of her nipples. They were large and erect. She reached out and pulled us both down to them and we each took a nipple in our mouth through the sheer material. I couldn't recall ever sucking a nipple this way and knew I had surely been missing out up until then. It was a wonderful twist to suck a nipple through the thin diaphanous material. Chrystal moaned and supported them with each hand as we sucked and nibbled them. I wondered what it must feel like to have such wonderful tits sucked simultaneously. Her soft moans confirmed she was enjoying it. I know I was.

She finally pushed us away and unzipped her leather skirt. She kicked off her heels and let it fall to the floor. I could smell her musky scent already as a wet spot was evident at her crotch. She certainly enjoyed our attentions to her nipples. The panties were high cut and had a panel of Lycra and lace that contained her lower abdomen. She looked beautiful in her sheer bra, the nipples wet and lipstick stained, the wonderful panties and stay up sheer hose she still wore. My cock hurt just from being in her presence.

Chrystal stepped back and put her heels back on for effect. She took a seat on a bar stool, picked up her margarita and said "Suck your cocks for me girls. I want to see a show, but if anyone cums I'm going to be very unhappy with you." She handed Lisa a pair of scissors from the bar. I was afraid for a brief second, until Lisa used them to cut an opening in her pantyhose for her cock and pulled it out. He handed them to me to do the same. What a crazy couple. I thought to myself 'they should be making movies'.

With my cock now exposed, Lisa dropped to his knees to take me in his mouth.

"No, wait!" Chrystal exclaimed. "Your little cocks are almost twinsies. Make them kiss for me." She had had a moment of tequila induced inspiration apparently. So Lisa stood back up and we touched our cock heads to each-others. It was a strange evening, to be sure.

"Oh, isn't that cute, I think they like each other," Chrystal laughed to herself.

Rubbing our cock heads against each other, slick from pre-cum, did feel very good, I agreed, and awfully embarrassing to do so in front of a woman. Lisa kissed me, then dropped to his knees and took my cock in his mouth.

He sucked it hard from the time his lips took the head, all the way down it's length. I could feel the head hit the back of his mouth and keep going. He hardly hesitated as he took my cock entirely into his mouth. He pulled it back, and did it again. Then pulled back and sucked the head and tickled my urethra with the tip of his tongue. That was all I could safely take and I put my hand on his head and nudged him back from me. He was an excellent cocksucker.

"Okay, your turn sissy girl," Chrystal said, and Lisa stood back up on his 5" heels.

I knelt down and took his hard cock in my hand. It felt different from holding my own as I kissed the head and touched my tongue to his urethra. I could hear Chrystal telling me to go deeper as I tentatively sucked the head. I did my best to copy Lisa's technique, but felt my gag reflex as I tried to take him all the way. I couldn't mimic that, so I sucked him like I was thirsty and hungry for his cum and his response told me I was doing well at my first true blow-job. I was so proud of myself, considering my history. They let me work his cock for what seemed like several minutes. I wasn't that good, or he had good staying power. One, or both, I didn't know.

Chrystal finally told me to stop and that I had done a very good job.

"I want some little cocks in me," Chrystal stated, setting her glass on the bar. "You girls take your wigs and lashes off, and everything else and meet me in the shower. We don't want to ruin them." She got up and swung her hips towards the bathroom, kicking her heels off as she went.

Lisa led me to a small bedroom off the main room. It had a small bed and dresser with mirror and we stripped and removed our hair and lashes. We made quite a sight. Two hairless, made up men with matching hard-ons bobbing up and down as we made our way to meet Chrystal. It was all very bizarre, and terribly exciting at the same time.

We found Cheryl naked on a small shower bench, about 3 feet square, in the middle of the large shower enclosure. The floor was heated and it was surprisingly comfortable as we entered the enclosure. A black object with a medium size bulbous head lay next to her on the bench. I recognized it as an anal probe.

Chrystal rose and said to me "Lie down, Sissy," as she guided me onto the bench and onto my back. She positioned me such that my hips were on the edge of the bench and climbed on top of me. She kissed me, then found my hard cock and guided me into her wet pussy. She was more than ready for me. I held her huge firm tits as she gently rode me for just a few strokes to open herself.

She stopped her movements completely as she sat on my cock buried to the hilt inside her. It took absolutely no effort on her part to take me entirely and she just sat there on top of me and smiled. "We're going to pop that little cherry of yours sissy boy. You just hold still now."

I watched as Lisa used a liquid soap dispenser to lube the head of the probe. When I lost him from view I felt his hands spreading my legs apart and feeling for my anus. He found his mark and gently applied pressure. Chrystal looked into my eyes as I felt it pushing. She held my shoulders to the bench and made a pout face. "Relax sissy boy, it will be better soon," and the head of the probe spread me and entered. It was painful at first, to be sure. Lisa massaged my thigh and Chrystal pressed against me and kissed me as it probed me further. She parted her lips from mine as she felt the tension in my body ease.

I focused on Chrystal's magnificent tits and full lips as she rode me. Lisa stopped pushing on the probe at that point and Chrystal held absolutely steady on my cock. I wasn't ready for what happened next as I felt a cock slide next to mine through Chrystal's fascia wall. Lisa had entered her ass, with mine in her vagina, and Chrystal purred as two cocks filled her. She seemed to love it and started riding us the best she could as we adjusted to her rhythm. She rode us like that for just a couple of minutes, and then Lisa started working the handle of the anal probe in me and hit my prostate. I nearly screamed and came shortly thereafter. I had been refraining from masturbation for several days and relished in my orgasm. It exploded from inside me and I bucked against Chrystal's pussy until I was spent.