Life After Last Night

Giddy and gay I'm on my way to Jenny's house. My wife, Sheila, is out of town on one of her bi-monthly business conferences and for me that means a Saturday night date. My friend Jenny has a salon in her home and for a guy like me that is ideal.

It's 9:00AM and I've been up and busy for three hours. I started a liquid diet Wednesday when I confirmed the date, but for me – date day means a deep douche.

Among my stash of "special things" is a rig designed for just that purpose. It consists of a pair of two-quart douche bags with individual control valves and a common "Y" connection. The "Y" connection delivers fluid into my body via a double enema bag. This little darling allows one to take two quarts and then writhing in pain, take two more.

While I soaked in a bubble bath and shaved my body this morning, I took four sets of double bags. I can't really get four quarts in me, but once I get past the initial bag I can get more that three in me. I hold them ten minutes before releasing them. I'm clean of course, but I'm not clean enough for a date. When I expelled the last set, I shoved a soapy washcloth inside me where it now resides.

Speeding along, I'm dressed in a gaff, lace panties, white short shorts, a lacy sports bra, a short pink tank top and flip-flops. This might be considered the wrong outfit for a guy to be speeding in, but I've become quite bold with my feminine dress. I'm not passable as a girl under any circumstance, but I love being observed as a transvestite. I was stopped for speeding a few weeks back and the young officer made me get out of the car and stand while he called my information in. He was nervous as a cat and I think he thought he was punishing me in some way, but I thought it was a hoot.

"Hi, Jamie Jo." Jenny said with an affectionate hug and air kisses. She knows and always uses my "fem" name when we are in private. As far as that goes she knows my real name, Jim Carter, as well. Holding my arms out she says, "You're cute as a kitten."

"I'm just a guy in girls clothes. You're the doll." I said. Jenny is four inches shorter than me at 5' 6". She has beautiful features enhanced by impeccable makeup. Her body is boyish with small breasts and narrow hips, but her legs go all the way to heaven.

"We're all set inside. Have you eaten?" Jenny Asked.

"I'm not hungry, but is it too early for a light beer?"

"I've got some cold, just for you." Jenny said. "What's on the agenda?"

"I have a date tonight. I want a face wax, a manicure, a pedicure and my wig washed and styled." I answered as we went inside and I got seated.

"Who's the lucky guy?" Jenny asked, trying to be obtuse.

"Fred." I answered with a glow despite knowing Jenny hated the guy.

"Girl, you can do without that asshole." Jenny said.

"How's Holly?" I asked trying to change the conversation.

As if on queue, Holly walked in. She was stark naked and said, "Hello, sissy boy."

She is a stunning beauty with alabaster skin, strawberry blonde hair and wide hips. She has a very flat chest, but huge areolas. I couldn't keep my eyes off her. No question I would give one of the legs off my stool in hell to look like her.

She walked over to Jenny and kissed her. Jenny ran her hand slowly up Holly's leg then touched her soft amber curls. When the embrace ended Holly looked at me hard as if to say – hands off. But I know the deal here and I respect it except in my fantasy world. Here's a question, if a tranny makes love to a woman is it heterosexual? What if the woman is a lesbian?

Holly slipped on a short robe and volunteered to do the waxing. I don't believe she's a real top, but she never misses a chance to deal me a little pain. While Holly waxed my face Jenny did my wig.

Before they started on my nails I asked for a potty break. I removed the washcloth from my tail and put it in a zip-lock bag I had brought for the purpose. The cloth was relatively clean. I leaned over the tub and took a fleet enema. When it was expelled I inserted a super tampon and rejoined the girls.

I finished my beer and had another while they did my nails with French tips. Jenny and Holly don't drink. I think they might be in AA, but my drinking has never been an issue. We prattled pleasantly about clothes and makeup and a new mall east of town. Jenny kept up her never ending quest to hook me up with a new man.

By the time Jenny put my wig in place and started my makeup it was approaching noon. My wig is a platinum blonde bob and Jenny was applying light tan shades to my eyes. I would use blue green later, but what she was doing would attract a lot of attention as long as I was an obvious male. She applied eyeliner, curled my lashes then colored my thin arched brows. My wife Sheila had a fit when I pierced my earlobes, but Jenny had plucked and shaped my eyebrows over several visits. If Sheila noticed she didn't say anything.

Speaking of my wife, my life with Sheila is pleasant. She refuses to be in the room with me dressed in women's clothing and bitches constantly that I appear gay. I don't have a clue where she gets that notion. I've been on a light regiment of female hormones for two years, I'm very careful about my weight and I do toning exercise daily. As a result, I'm thin with a flat belly, tiny breasts and smooth hairless skin. I have a fair complexion and stay out of the sun. As previously stated my ears are pierced in three places and my brows have been plucked. I wear my hair short and men pay these little idiosyncrasies no mind. Under my white shirt and tie my pierced nipples, naval ring and the butterfly tattoo on my right shoulder would shock them, but otherwise I'm just another smuck.

I told Sheila I was having erectile dysfunction and in fact that is the truth. The hormones seem to have reduced the size of my equipment and it takes a lot of work for me to come. Sheila wanted me to take Viagra, but didn't seem too unhappy when she had to settle for cunnilingus. It's a good arrangement. I like to give and she likes to receive. She makes an occasional run at my cock, but it is truthfully a waste of time. It takes me 20 – 30 minutes to jack off if I have lots of visual stimulation.

Jenny has a shaded patio so we sat outside and ate a light lunch. I had yogurt and they settled for fruit and cheese. After lunch I combed my hair, put the wig in a case and said goodbye in Jenny's favorite way – a stack of twenty-dollar bills. Jenny warned me to be careful and she wasn't talking about riding around dressed as a girl. I got the message but my blood was hot with lust and building.

Chapter Two

Back home the next order of business was a nap. I removed the tampon and replaced it with a heavily greased medium butt plug. After slipping into a floor-length flannel nighty, I set my alarm for 4:30, took a sleeping pill and settled into bed.

Upon awakening a jolt of reality ran through my limbs. I could hardly contain the joyous thought that I would soon be in his arms. My high-heel mules clattered across the floor as I began my packing. Jazz music and Scotch whisky aided my happy task.

I packed one gaff and set one out to wear. My panties are pure spandex and lace high cut briefs. I prize them for their beauty and utility as additional restraint. I packed two pairs of white and kept one out. My garter is smooth white satin with three adjustable straps per side. I added the garter and two pair of white hose with seems up the back to my bag. My brassieres are spandex and lace matching my panties. They are front closure with "A" cups, which my tiny breasts barely overflow.

When I wear a bra (which is often) I wear elaborate silver nipple shields. That thought in mind I pulled my gown off and sat down at my dresser (another item that got Sheila's dander up) to install them. When they were new the barbells in my nipples were difficult to remove and replace. These days I've graduated to 10-gauge studs and they are stimulating to remove and replace. My nipples must be pulled through the shields before the studs are put in place. That task finished I stand and admire my beautiful slender body made more perfect by its feminization.

The thought occurs that covering this creation would be in bad taste. So I decide to finish my packing in the buff, but something is needed. I have a fat black butt plug from which two-feet of chrome plated chain dangles. I run to the bathroom and make the exchange. When I return to my packing the chain bangs the backs of my legs and wiggles the plug.

I pack a white bra and keep one out. My dress is lovely, but I'll describe it later. It goes in a hanging bag. I'll wear a highly starched, white, man-style shirt and white shorts to the Motel. A yellow scarf will add some color at my throat. White leather flip-flops with ½" heels show off my new French tips. I get short of breath just thinking about wearing this outfit, about going outside in it, about being seen in it, about talking to someone in it.

A trip to the kitchen with my tail jangling is rewarded with a shot of Scotch made civil with a splash of soda. Then it is back to packing.

My restraints and paddles are kept in their own case. My skin burns as I place the case in my bag. I willingly provide Fred with the tools to hurt and humiliate me. I'd like to say no to my madness, but instead I caress it and eagerly await its evil spell.

My makeup case fits snuggle inside my bag accompanied by a two-quart enema bag and a feminine sprinkle. My dress shoes are in a cloth bag. I include a yellow two-piece swimsuit and yellow wedge-heal sandals. The last item is my gift to Fred and my case is ready to go.

Since childhood "dressing up" has been my greatest thrill. My mother's tangerine shorty nighty flickers in my mind as I slip my arms into my bra pull it across my chest and snap it shut. After I replace my dangling chain with a tampon, my powdered genitals rest comfortable inside my gaff. My panties are more natural than my skin. Each button on a girl's shirt is special when you're a guy. Shorts seem even shorter when they zip in the back. Somehow my yellow scarf reminds me of a boy scout. Dressed like this I guess I am scouting for boys. I comb my hair in a normal male style, put a tiny gold stud in the upper hole in each ear and fill my purse.

Purses are uniquely feminine. This one is a white leather shoulder purse with a big non-functional yellow bow. I carry a small jewelry bag, my wallet and keys, a delicate handkerchief, two tampons and twenty condoms.

A last minute look in the mirror revels a trim reasonable nice looking male in feminine attire, an obvious bottom, and an obvious tranny. It was just the look I wanted. I loaded my suitcase and wig case in the trunk of my convertible, donned a pair of sunglasses with big, round, white plastic frames and set off on my adventure.

Chapter Three

My first stop is the grocery store down the street from our house. Shelia would faint if she knew I was going into "her" store dressed like this. She would assume every person she knew would see me, think I was gay and never speak to her again. Of course, the likelihood of seeing someone I knew was remote, but my heart didn't seem to realize that, it was pounding out of my chest as I swung my bare legs out of the car. I had to pause a moment before I stood.

I had a shopping list in my purse, but Fred required me to spend at least 30-minutes in the store. He wanted a cheese ball, beer and crackers. For their embarrassment value I was to buy a box of super tampons and two boxes of condoms. I also had some items I needed including a large jar of honey, fresh flowers, plastic cutlery and small paper plates. I decided a slow trip through the store pushing a cart was the best way to use my time. After my heart rate dropped, I began to enjoy the trip. One guy actually came up behind me and patted my ass with his wife three-feet away. I got a couple of soft whistles and the sack boy complimented my toenails. The good news was nobody followed me to the parking lot and kicked my ass so all and all it was a fun trip.

My next stop was a mandatory trip to the mall, I didn't bother telling Fred I was a mall rat. I was supposed to visit at least ten perfume kiosks and shop for a new fragrance at each. The hook was that I was to go to the men's room and wash the odor off between visits. I was to linger in the men's room and establish eye contact with every male that visited. If they made an offer I was to comply.

On my fourth trip a college guy asked if I had real tits? I allowed him to reach inside and find out for himself. The nipple shield startled him, he mumbled something and left. He must have followed me around because on my seventh trip he was back and this time he had a buddy.

"Do you suck cocks?" The buddy asked straight out.

"Yes, Sir." I replied.

The sir got him going. "I want you to suck mine." Then as an after thought he added, "And my friend's."

"Yes, Sir." I said as I turned and walked to the handicapped stall at the end of the row. I was on my knees when the buddy entered the stall. I helped him open his jeans and pull his cock out. I put a condom in my mouth and by the time I rolled it down his shaft he was ready. Bringing a young man off is easy and I am very good. I sucked him hard and deep, fondling his balls and rubbing his chest. When I reached between his ass checks he blew like a gusher. He'd been in my mouth less than two minutes.

College guy was shaking like a flower in a storm, but his meat was extraordinary. Long and fat it was more than a mouthful. I didn't give him a time to think.

I put a condom on him, stood and turned around. "Please unzip my shorts."

He did and I stepped out of my shorts, panties and gaff. Had I asked him to pull out the tampon, I'm sure he would have run like a gazelle. Instead, I put the foot closest to him on the toilet and slowly removed the cotton cylinder. Both feet on the floor and my back to him I bent at the waist exposing my hairless pink pussy. Even a college boy knew what to do from there. The lubricated condom glistened as it found a home. He started in slowly then reached for my hips and pushed home. His cock had probably never been in such a warm tight spot. I didn't count but I don't believe he made as many strokes as he was years old. Once he was satisfied, the heat of the moment gave way to shame, he jerked the rubber off, threw it in the toilet and left without cleaning himself.

I on the other hand, I had some cleanup to do. Using toilet paper and water from the toilet I cleaned my pussy, put a fresh tampon in and put my shorts and underwear back on. I had dirt on my knees, but soap and water from the lavatory fixed that. I repaired my tan lip-gloss, combed my hair and went back to shopping.

My next trip to the men's room found a security officer waiting on me. I'm not a conspiracy theorist, but sometimes it seems like big brother is watching. He wanted some identification. We went through the whole "why do I have to give you ID" conversation, but he persisted. He puffed up like a blowfish when I opened my purse to show him my ID. I think he puffed up in lieu of thinking up something to say. His next trauma was my simple explanation that I had come to the men's room to wash the perfume of my wrists. He left the room without telling me not to feed the animals or suck their cocks.

My last two trips were uneventful and I'm almost embarrassed to say that I settled on Britney Spears Fantasy perfume, but that was the choice. As I was leaving the mall, "The Buddy" saddled up beside me and told me he needed a repeat. I was only obligated to suck cocks I met in the men's room and Fred hadn't told me to do repeats. I told the idiot I'd meet him in the men's room at the other end of the mall. The last time I saw him he was following his dick in that direction.

The wind in my hair and up my shorts was refreshing as I headed to the motel. It was an older low-price place selected specifically because I could get an outside first floor room. I knew why this was important, but I didn't want to think about it now. I was only a few hours from love.

The lady on the front desk was put off by my appearance and my purse, but resisted the temptation to comment about my use of the room. She put me on the backside of the complex without my asking for that area.

I moved my stuff into the room, got some ice and iced down the beer. I also put the cheese ball in the cooler. I went up front and borrowed a tablecloth for the small table in our room. I set the table next to the only lounge chair in the room. I put the flowers, plates and cutlery on the table.

It was time to get in the tub and time for more deep douches. The room and tub were small, but the water was hot and I had scented oils for this session. I got the enema bag in place and inserted two-quarts of warm soapy water into my body. I soaked in the warm slick tub water as the soapy solution wreaked havoc inside me. By the time that first douche was expelled I really wanted a second. Even the third one didn't satisfy my hunger but time was getting away. I put a tampon in me mostly to soak up residue. I put lotion on my arms, legs and torso and lay down for a moment to cool down before I dressed.

It was time. Out came the tampon – then lying on my tummy and utilizing the feminine sprinkle I pumped my pussy full of honey then plug it. Bluish green eyeliner enhanced my eyes. Red lip-gloss was over-the-top, but required in this instance. My garter and hose preceded my gaff and panties for obvious reasons; my bra followed them. My shoes are yellow single banded strappy sandals with ankle straps and 4-inch heels. My dress is a white shirt-dress that buttons all the way up the front. It has big yellow spots and a three-inch matching belt. I'm allowed four rings and a silver necklace. I'm required to wear one stud and two loops in each ear. With my wig in place, I'm a pretty transvestite.

I walked around outside our room watching normal people go about their normal lives. I could have walked away. I knew what was coming. Is it better to have loved badly than never to have loved at all?

Fifteen minutes before Fred was scheduled to arrive I set the cheese ball, crackers and Fred's present out. While I sat on the bed, classical music from the small radio added drama to my wait. A rap on the door jerked my into the present and launched me toward the door. Fred was framed in the opening. Dressed in gray slacks and a navy blazer he was sophisticated and beautiful.

Offering me a single yellow rose he said. "Jamie, you are more lovely than my gift."

I melted into his open arms and offered myself. His lips were firm and warm, his embrace patient. When he broke the kiss he moved to my neck. His lips sent a charge through my nipples and I purred instinctively. "I love you."

The moment broken he stepped into the room and shut the door. "I love you too."

He removed his coat, handed it to me and took a seat. "I'd like a beer and you in my lap."

A rapid respond team would have been proud of my time as I smoothed my skirt and settled into his lap beer in hand.

"Your beauty is only exceeded by you willingness to serve." He said as he held me and presented me with another more urgent kiss. "I want you, but let's go slowly the night is young. Besides, who's the present for?"

Sliding to the floor at his feet, I hand him the box without a remark being careful to run the back of my hand across his crouch.

"Flirt." He said.

"Meany." I responded.

Fred took a sip of his beer and began to open his gift. "O, baby. It's wonderful. We'll put it to good use later." He leaned over and kissed me then added. "Walk around for me."

I stood and walked back and forth the length of the room, the sway of my hips a practiced precision.

"Now, slowly remove your dress and show me again." He said.