Of Course The Offer Still Stands

(Disclaimer: All depictions of sexual activity occur between consenting adults over the age of 18.

Please be aware that this is a slow meandering story at the outset. Thank you in advance for your time, should you decide to spend it here.)

Of Course the Offer Still Stands

The time was finally near. After all the failed, halfhearted attempts to pursue my desires, it was finally going to happen. We had met on a Yahoo Groups board back when just about any fetish or kink known to humankind could be found there. Some really nasty, ugly things that I was pretty sure were illegal in most states. My particular interest was cross dressing/transvestism and Sissy Maids in particular. It's a quaint little hobby compared to some of what could be found in those groups at that time. It was an interest Ms. Sheri and I shared. I had been fortunate enough to find her there among the detritus of humanity. The group might have been so specific as 'Sissy Maids in Corsets'.

We've crossed paths on a popular cross dressing site since the events I'm about to describe. I had posted a photo of myself from that first meeting as a profile picture there and received a message from her; "Hey, that's my living room. That picture was taken in my living room." We had a brief electronic exchange, but never really connected again.

I can only hope she will enjoy this story should she stumble upon it someday. I'd like to think she would anyway. One more item to clarify; this was not an act of prostitution. Ms. Sheri was providing me with a make-over service. That was always the expectation from the outset. The only thing that might have been illegal about it would be practicing cosmetology without a posted license.

You might be thinking to yourself - 'this is no big deal'. To me, it was a very big deal. First, we had communicated a while, but it had been all digital up until this dark Sunday night. I was fearful I could be being set up for rape, robbery or murder. It happens. Ms. Sheri had texted me her address earlier and we had spoken just once or twice over the phone. When I found the address it was a dark, older home at the dead-end of a residential street butted up to the Interstate. It wasn't the best neighborhood and one that had had it's character destroyed by an interstate long ago.

Her home was mixed in with much newer duplexes and such. To let you envision it, think "an old lady lived and died here and the yard hadn't been kept up for the last 20 years." It's a common sight in much of suburban America.

Scenes of 'Silence of the Lambs' ran through my head as I made my way up the stairs and rang the bell. I'd left my drivers license and bank cards hidden in my vehicle, just in case. I'm a cautious sort, always over thinking things. Some people say I have "trust issues". In documenting this, it occurs to me there was an email trail, phone records, a text. Maybe I do have trust issues. On the other hand, it would be a perfect location to house a sex slave in the basement. The freeway traffic would drown out the sounds of the screaming.

Ms. Sheri greeted me at the door in full dress. Regalia might be a better word. She had a huge teased hair-do, long blood red nails emerged from open fingered black gloves, the highest of heels, incredible stage make-up, and, I honestly don't remember what she wore for clothing anymore. Some sort of tight dress, or top and tight skirt. She was definitely corseted.

She later shared with me that she had a huge Peggy Bundy infatuation/fetish, which explained the big pile of teased reddish orange hair. She presented a wonderful, polished, Drag Queen appearance.

The interior of the house was what one would have expected from seeing the outside, twenty years or more prior. The wall trim, door frames and built-ins were of aged dark wood, the furniture was of high end antique store quality and it appeared to be spotless. She later told me we were running late tonight as one of her sissy maids with an English Maid cleaning fetish had just left that evening and she was making room in her evening for my visit. I expect Ms. Sheri was the payee in the arrangement, though she didn't elaborate. It was all very odd, and excitingly real all at the same time.

Her demeanor matched her appearance entirely. The voice, her manner of speaking and mannerisms. She was the complete package and I could see her taking the spotlight on stage then and there. My wariness of the situation was fading and I decided this evening was going to be just what I'd hoped it to be.

Ms. Sheri gave me the once over and said I had great potential. I'm small framed, though at 40 years old, I no longer had the same waist size I had in high school. I have nice legs and thin little ankles and my freshly shaved legs felt good in the pantyhose I was wearing.

My thin ankles make my thighs look more fleshy than they actually are, giving me an overall feminine appearance. The downside was my weak calves made walking in the heels she chose for me that evening embarrassingly difficult. I'd worn heels of course, but nothing near 4".

A small bedroom off the main room served as Ms. Sheri's beauty shop. It was well outfitted with a make-up table and mirror, shelving with a significant number of wigs, make-up cases and shoes. She started on my eyebrows, encouraging me to let her shape them. I didn't allow her to do much, so she pasted over them and using spirit gum on my forehead, lifted them up off my brow line. It was already becoming a process. She opened a very large make-up case and started to work on my foundation. This wasn't make-up found at the local drug store either. It was professional in nature, with seemingly endless colors of creams, powders, pencils and such. It was not Maybelline.

Ms. Sheri worked and worked, chatting the entire time about this and that. How things had changed in her time. How people just took your money now, instead of calling someone a fag and telling them to get the fuck out of their store, as had been common in years past. We appeared to be similar in age, with completely different life experiences. Ms. Sheri had lived life in the drag scene; a lifestyle very different from mine.

I told her about me, my early interest in dressing and sissy maids. How I was familiar with the drag scene from a distance as I'd ordered publications from Lee's Mardi Gras of NYC. How magazines such as Drag, EnFemme and F. M. I., were like trade journals to me and I gravitated towards cross dressing and transvestite fiction novellas and such. Sissy porn, in other words. I had owned one maids dress I'd purchased from Lee's, but lost it in the purge after my arrest. I was starting over.

"Arrest. What were you arrested for, Dear?"

Oh yea, that part.

I shared how I had only met one cross dresser in my life up to this point. She was somewhat well known around my old home town as she had a strong penchant for exhibitionism.

I had happened upon her twice. Once at the grocery store, where I watched some young teens harass her in the parking lot. It was one of the first warm days of spring and I spotted her in the store wearing her spring outfit. 3" cork wedgies, pedal pusher pants and a ridiculously large pair of fake breasts and big hair. I mean EE kind of things. They were head turning large and worked well for her goal of drawing attention to herself.

I waited for her to exit the store and watched as a few adolescent boys started calling out "Are those real?", "Wow, those are big boobs," etc.. She ignored them entirely and then took her time placing her groceries in the backseat of her car, soaking up the attention. Her ass wasn't bad really. I don't know if she was aware of me sitting in my car watching, but I watched it all.

The second time I saw her was that following winter at the local mall. It was very early on Sunday morning and the mall had just opened. The time of day I preferred to be there. I would buy some feminine articles for myself, on occasion, during such shopping excursions.

I heard a distinct click, click, click. The unmistakable sound of stilettos on a tile floor. The sound could be heard throughout the entire concourse. It was like the sound of a chirping bird to a cat for me as I sought the source of it. She was dressed to the nines in a tight, mid-thigh length skirt, silk or satin blouse, big hair, and a pair of heels only the most skilled could wear with confidence. Her calves were taught and muscular. The way calves look from spending many hours in 5" heels I thought.

She turned the few heads present when she walked along window shopping. I stalked her. I wish I wouldn't have. She was probably aware of me. She stepped into Victoria's Secret, of course, and I took up a seat in the food court nearby. My heart raced and my palms were sweating.

I approached her as she exited the store. She towered over me in her heels.

"You look beautiful this morning," I said.

"Why thank you, so much," she replied with a practiced female pitch.

"I'd really like to get to know you?" I said. So sophisticated.

She looked me over and said "I bet you do. If you really mean that, then follow me, dear," and she headed towards the mall exit. I followed her at a cautiously safe distance. I still recall the nerves it took me to follow her, but I didn't care. I wanted to get to know her in the worst sort of way, no matter what lie in store. I was like a moth drawn to a porch light on a summer night. As it turns out, it was more like a moth to a flame.

She walked into the open air parking garage with her heels still making a clatter, to a white 4-door car. It was odd looking, Italian maybe, and probably the only one in half the state. I realized it was another attention getter. As I approached from behind, she unlocked the doors and sat down in the back seat with her legs hanging out so that her feet were still on the pavement.

There were other cars parked adjacent to hers, providing some level of concealment and she called to me, "Come closer."

As I stepped between the cars so that I could see her sitting there, she lifted her hips and hiked up her skirt and pulled a sizable penis out of her panties. "Is this what you want, lover boy? Go ahead, show me how much you want to get to know me."

I hesitated as she stroked the length of it with immaculately manicured nails. Her large testicles were evident in the high end panties that encased them. I wanted to pet them in their Lycra glove. Lust overcame me and I got on my knees and took her cock from her and engulfed the head in my mouth. It was the first time I'd held another cock since I'd reached adulthood and the feel of it was intoxicating.

I worked her stiffening cock with my mouth and brought her to full erection. She wasn't a petite person, nor was her cock. It nearly filled my mouth and I had difficulty working my tongue around it. I was beginning to taste pre-cum over the first tastes of talc, when I heard someone speaking.

"All right, break it up. Break it up," said the Mall Cop standing at the opening created between the cars. As I released her cock, my first instinct was to run. The door of her car wasn't going to allow that very easily. I was cornered and broke into a cold sweat.

As I stood, the guard was talking. "We told you we weren't going to let you slide again, and that was only three weeks ago. Here you are doing the same shit. We're done putting up with this. You're going downtown this time."

He looked at me and said, "You're in the wrong place at the wrong time. I hope it was good for you"

She started giving him the "Fuck you Mall Cop" routine when the police cruiser pulled up. We both took a ride downtown in separate cruisers and were booked on public lewdness charges. Once the police report came out, it quickly led to divorce for me.

My wife had tolerated some dressing on my part over the years, but sucking cock in the mall parking garage was a bit more than she was willing to deal with. Just the public nature of it had forced her hand. How could we really stay together after the gossip started? We didn't, is the short answer. She had a daughter, Emily, born before our marriage, so we had no children to fight over. Emily was more empathetic to my situation actually and we still keep in touch.

My job became unbearable as a result of the incident as well. An arrest record for public fellatio with a cross dresser tends to have that effect. That's how I ultimately found myself on the other side of the country and in Ms. Sheri's setting room. If change was inevitable, I decided I might as well try and make the best of it. I was now a sex offender in the state of Iowa anyway, but at least it was only a misdemeanor and I could still seek employment elsewhere.

"That's some bad ass luck, Hon. Damn," Ms. Sheri said after I'd finished. "Let's put that in the rear view mirror tonight." She continued applying her craft and I tried to sit quietly at this point.

Her false eyelash collection had an impressive array of options. She picked one she thought would suit the look she was after and glued them over my own. Their application seemed complicated, but wearing them wasn't as cumbersome as I expected. I wasn't allowed to see the results of her efforts, just yet.

Once she was satisfied with my face, it was time for corseting. I had worn my own cinchers and the like over the years, but not a real corset. I enjoyed the feeling of the constriction as much as the effect they had on my figure. It's hard to explain to those unfamiliar with the feeling it invokes. The corset Ms. Sheri had me step into was not a lingerie, just for looks, kind of garment. It was made of heavy cotton and a massive amount of stitching for the stays and laces. It was a classic under-bust Victorian model and looked like it was made to wear for a contact sport participant.

I raised my arms over my head and laced my fingers together as instructed and Ms. Sheri tightened the laces. I'm sure the corset was capable of a greater waist reduction, but Ms. Sheri advised that it took time to adjust to wearing a real corset. It still impacted my breathing and I noted it would be great for my posture. Wearing a true corset caused me to think of a female bosom spilling and pulsing out over the top of a over bust model. I now felt for myself the reason for the rise and fall of the exposed upper breast being the visual effect of forced shallow breathing. I loved it, even though this one didn't provide that appearance. Perhaps another time, I thought.

I was then fitted with a bra consisting of full cups and overlaid with intricate lace stitching. It was a full C cup. Ms. Sheri produced silicon breast forms from a container and assisted me in adjusting them in the cups. I'd read of other cross dressers opinion that true breast forms were a must have, been had never purchased any for myself. The weight and bounce they provided convinced me of their appeal. I decided I must have a pair of my own, and soon. I loved the weight and jiggle.

Ms. Sheri helped me slide a short black satin slip over my head so as not to mess up her makeup job and I smoothed it over my torso. It added a wonderful contouring effect to my improved feminine shape and I would have been happy not to add any additional clothing.

Ms. Sheri then produced a ridiculously short, royal blue maids dress. My first impression was the unusual fabric. Ms. Sheri explained that it was made of acetate and not a cheap item. The second impression was that it would not fit me. She assured me that it would and had me step into it and pulled it up. I felt a chill as it slid up my legs and over the slip. It was gorgeous. I noticed the arm pits had some appearance of being bleached out and it was apparent it had seen some wear. Ms. Sheri zipped me up as I admired myself. My heavy breasts, my cinched waist, my smooth legs. I felt so feminine. I find it difficult to convey the feeling being dressed like this invoked for me.

A hair cap and shoulder length dark brown wig was then added, the strands or hair caressing my cheeks. Ms. Sheri spent several minutes brushing and arranging it before she was satisfied with the look.

Then came the shoes. I had only owned 2 ½ or 3" heels previously and these appeared to be 4". They were classic black pumps and showed some wear. Ms. Sheri commented on how the toes had some scuffing, and there's only one reason the tops of toes get that way. There had apparently been a certain amount of cock-sucking done by previous wearers of them. I was enthralled with the look of them on me. My slim ankles were angled down and my toes were wedged in to them in an exquisite way.

I tried to stand and take a step and my legs wobbled and Ms. Sheri had to catch me. She laughed and said "I thought you said you'd worn heels before?"

"Not like these." They made me feel incredibly tall as I stand about 5' 9" normally. I was now over 6' and it made a drastic difference in my perspective to the floor. I was able to navigate my way to a floor length mirror. Ms. Sheri had kept me from viewing myself and I was shocked at my appearance. I was sexy. I was beautiful. It had been worth all of this. My cock stirred and expanded in my panties and hose.

All I could say was "Thank you."

Ms. Sheri said "I've impressed myself I think. You're the cutest one I've had in quite a while."

"Really. You think so?"

"Oh, yes dear. I know some people that would love to spend some time with you. All sexy and cute, and practically a virgin."

"I'm not a virgin," I replied, then I thought 'oh, that kind'. Then I asked "What kind of people?"

"Lot's of people. A few transsexuals I know would love to break you in, dear. Cute virgins are hard to come by these days." There she went again with the virgin. It was quite distracting.

I had to agree, I did look good though. My nose and facial features in general had allowed Ms. Sheri to create a wonderful illusion. The lyric's to Lou Reed's 'Take a Walk on the Wild Side' ran through my thoughts.

We then did pictures with a digital camera. Ms. Sheri then connected the camera to a monitor on the Setting room wall. It was out of place in the otherwise traditional decor.

My favorite was one where I was seated on a straight back Victorian style dining chair with my legs crossed and the dress riding up my thigh. My left leg was crossed over the right and showed off my svelte ankle as the shoe dangled in the foreground. My waist was narrow and my chest was voluptuous. I looked as feminine as I ever had. The photo was to be masturbation fodder for me for over a decade afterward. I was a sissy maid. I wasn't me anymore.

What transpired next is embarrassing to share.

Ms. Sheri said "So that's it. You just want to prance around looking girly then?" and looked me in the eye.

I knew what she was getting at, so I told her. "I want to put your cock in my mouth." I didn't say I want to suck your cock.

So Ms. Sheri obliged me and I took the semi-erect penis she presented to me and held it in my hand as she photographed me. I kissed the head and put it in my mouth, all captured for posterity. I didn't get a full erection from Ms. Sheri and I wasn't really trying terribly hard to do so. It was minimalist fantasy fulfillment and that was the extent of it. Ms. Sheri understood it for what it was and we we both acknowledged and accepted that.

She had me stand in front of a mirror and pull my hose and panties down and squirted some lube in my hand and told me to get myself off. That didn't work either. I wasn't there to get myself off in front of her. I was certainly enjoying myself that evening, but jerking off looking at myself in the mirror wasn't what I was after either.

Ms. Sheri looked at me and said "You are a strange sissy. I don't think you know what you really want, beyond being a princess. I'd love to show you off sometime though, if you're willing to put in the effort."