Sheila’s Escapade #137


My beautiful Mistress is out of town for a long weekend. This is ostensible a semi-annual buying trip for one of the stores she represents, but in this day and time such trips have become arcane. I’ve always believed her real motive is to spend time with her friend Jan. The very thought of her between Jan’s legs and lapping away at Jan’s pussy made my clitty stick harden and drool inside my Bird Cage restraint. She has four girl friends she pals around with here. They have all seen me en femme and I frequently eat their pussies. I’ve never seen Mistress Rachael go down on one of them, but I know she loves to lay with women.

Late Thursday afternoon I began getting ready for my weekend of depravity. I give myself a pedicure and painted my toenails Strawberry Red. Recently, I’ve begun going to a local Mary Kay dealer for my manicures which end in clear polish. I haven’t yet worked up the nerve to wear my flip flops and let her do my toe nails. When I visit her home, I wear a blouse and side zip slacks or shorts, but so far she hasn’t asked and I haven’t told her I’m a Transvestite.

Next I relaxed in a scented bubble bath and shaved head to toe. I have very light hair growth and I keep my body shaved at all times, but the feeling of freshly shaved legs is just yummy. I always wear barbells in my nipples. On weekends like this one I add butterfly nipple shields and stirrups.

Mistress has the keys to my cage, but I really don’t object. Being caged frees me from the obsession to play with myself and helps me concentrate on my feminine duties to be of service the cocks of real men. The hole in the end of my restraint allows me to sound myself with a number six knitting needle. My arousal from the sounding is unmercifully and painfully restrained by the Bird Cage. Meanwhile, I douche over and over again with my feminine syringe and attach clothespins over the top of my nipple inserts.

I work from home so I’m frequently dressed all day, but on these special weekends I like to go out dressed. Friday morning I chose a white lace camisole, white panties, a white silk blouse and tan worsted wool slacks with a side zipper. I wore a wide brown belt, brown ballet flats without socks and I put all my essentials in a small brown clutch purse. I slicked my hair back in a severe “butch” manner. I used almost invisible pink lip rouge and no makeup. I wore a thin silver necklace, a ladies watch and an ID bracelet engraved “Cum Slut”. The piece de resistance was a faux diamond wedding ring set. The look was really more unisex than feminine, but I knew what I was and someone almost always noticed something and made a comment or touched me.

It is undeniably stupid of me to run around my home town dressed as a woman. I have family and friends I don’t want to embarrass and I’ve never been sure what actions the police can take if they are so inclined, but I’ve never been accused of being smart so I was off to the mall. I wanted some new clothes for my trip Saturday night.

At the third department store I found a very short chiffon skirt in multiple colors of rose, coral, gray and white. No sales person was around so I took it to a dressing room and tried it on. It is thrilling and I wanted to my very to wear it out of there, but alias that would have to wait for another day or another time. I retraced my steps and bought a white silk blouse I’d seen earlier. It had a wide collar and French cuffs. The young sales lady watched as I went to a dressing room and tried it on. As I emerged she knew full well what she was seeing. I wanted to offer her unlimited cunnilingus, but she rang up my purchase and I left. After that I went to the men’s room and blithely exchanged my tampon then sat in the food court and enjoyed a cookie and a cup of milk.

Back home serious preparations began for my trip to a local landmark and haven for cocksuckers – The Apache Drive-in. They show suck & fuck movies, but that is window dressing for the real activities for which they are famous – real live sex. It is a beehive of activity with the aggressors literally driving around and parking next to potential compliant partners. If you want a cock in your mouth or up your pussy this is the place to be. My concern is STDs so I try to have a date lined up when I go. A date won’t stop the prowling, but it adds to the excitement when they park next to me and watch me service my man.

One of my favorite toys is my inflatable enema nozzle. I love having it in me and often detach it from the enema bag, inflate it and wear it. Its main purpose for that evening was to clean my pussy. In a hot bubble bath I connected it to a two quart enema bag, put it in me and inflate it. There is nowhere for the concoction in the bag to go but my intestines. Taking the first full bag is physically painful and I always add something like Tabasco to that batch. A fun combination is baking soda water followed by vinegar. Another old favorite is Morgan David wine. The second and third bags are usually much less painful and if Kurtköy Yabancı Escort number three run nice and clear I usually stop there. I concluded my bath by lying back in the warm scented bubbles and using my feminine syringe until my pussy is super sensitive and deep clean. When I emerge and put a super plus tampon inside me I am uncomfortable aware of its presence from the moment it is inserted.

I was to meet a guy named Dave. We had met for lunch a couple of weeks back as part of my ritual feeling out process for new dominants. We didn’t have sex at that time, but he is nice looking and an Alpha male.

I didn’t believe there would be a reason for me to get out of my car, but I decide it would be prudent to dress for the trip in white ladies shorts rather than a skirt. I wore panties and a cuff top brief. My caged clitty stick fit between my legs, but I wore a Kotex in my panties for added padding and comfort while sitting. My bra was a white front closure with soft “B” cups and I inserted “B” breast forms. My blouse was a pale yellow with three quarter sleeves and a wide floppy collar. It was designed to be worn outside my shorts. My accessories included a pearl necklace, a ladies sport watch and a pearl bracelet. On my right hand I wore a large pearl dinner ring and a silver thumb ring. My wedding rings adorned my left hand. My shoes were peep-toe, sling back heels with 4″ heels.

There wasn’t much I could do with my face so I didn’t try. I brushed my longish hair into gentle waves. My ears were not pierced; my face was smooth and soft, but devoid of makeup. I did wear strawberry red lipstick because my dates always want to kiss painted lips. My look was unmistakably that of a transvestite, but I didn’t stick out to the casual observer as I traveled to the drive in. The male in the ticket booth gave me a knowing eye, but I’m sure girls of my type are frequent visitors.

I arrived at precisely 9:00 PM, but I was unable to find Dave so I parked and began enjoying the movies. Predictably, in short order a large silver pickup truck pulled up alongside the passenger side of my car. I’ve heard it said the larger the truck the smaller the penis, but I have insufficient data for an opinion.

I sat quietly and tried to ignore him. The instrument lights of my car gave him an obscure view of my condition, but as I stated earlier he probably couldn’t tell I was a sissy faggot. These little mating rituals are normally short if the predator doesn’t sense he has a willing victim, but this guy was persistent. He finally moved his truck forward about four feet and opened his door. This was not his first rodeo. He had rigged his truck so his lights did not come on as he got out. He calmly unzipped his pants pulled out his cock and began massaging it.

I’m not sure what he wanted, but I wanted the cock. It was long and fat and irresistible. I flipped on a map light and rolled down my passenger window. The effect on him was mesmerizing. He stood there cock in hand, bathed in the pale light and drank in my slender female form. I asked what he wanted and he replied he wanted to fuck me. It was a perfect response.

I opened my door, swung my legs out and stood. Walking on the gravel surface was difficult in heels, but I made it. I handed him a rubber and while he fumbled around getting it on, I wiggled out of my shorts and panties to reveal my caged cock and cute round bottom. I leaned against the car, pulled the tampon and dropped it on the ground. The stranger was wild with lust. Without as much as a “fair thee well” he slammed his cock into my pussy and began a ferocious fuck.

The unexpected thrill coupled with his hunger brought him to a climax in a matter of seconds. He collapsed on top of me, kissing my neck and mauling my little breasts. As he softened I expelled him from my pussy and he professed his undying love for me. That love was to, of course, commence with a trip to a local motel. As I dressed and started back to my car he offered me $500.00 and I was tempted to take it, but fear and a momentary wave of good judgment steadied my resolve and I bid him goodnight.

Dave arrived shortly afterwards in a dark blue van. I gathered my things and joined him. We chatted amicably for a few minutes, but there was an edge to him I hadn’t seen before. His real personality was emerging. He told me to go to the office and buy him some popcorn. He allowed me to change into my ladies tennis shoes, but stopped me from removing my jewelry. I reached for my purse, but Dave said I wouldn’t need money as long as I had a mouth.

I felt like Little Red Riding Hood surrounded by Big Bad Wolves as I made my way to the office. Fortunately for me the clerk agreed with Dave that a blowjob was worth a bag of popcorn. So after a few minutes on my knees I returned to the van with the popcorn and the delicious taste of cum in my mouth. Dave wanted to see the seed before it was swallowed.

As instructed I stripped and put on a short red nighty Kurtköy Yeni Escort with spaghetti straps. He played with my nipples and my cage before removing my pearl necklace and replacing it with a choker chain. After we had moved to the back of the van he attached the other end of the chain to his belt and stated he was sure my mouth never wanted to be far from his dick.

From here the events were every subservient cum sluts’ dream. Dave put a probe with a wire attached to it up my caged clitty stick then attached wires to my nipples. He then put an inflatable dildo inside my pussy and cuffed my wrists to my ankles. He then apologized for having to move my mouth away from his dick as he unhooked the choker and strapped a cock gag in place. After being pushed over on my face thus putting my ass in the air, Dave handed me a plunger and explained that any time the pain from the beating got to be too much I could push the plunger and he would stop.

The beating began with a leather paddle. Other that my sit bones that type of punishment is not all that bad and I didn’t use the plunger. Dave decided to move on to a cat-o-nine. After a few minutes of this I pushed the plunger. Surprise, surprise a charge of electricity runs through my body from clit to tit. Had I been able to talk I might have told Dave that such a charge might stop my heart. I released the plunger, but the electrocution continued. My spasmodic jerking put my restraints to the test as Dave calmly sipped on a beer and watched.

This beating routine moved to a cane with pain so intense I finally choose the plunger as the lesser of two evils. I was bleeding, bawling and writhing in pain when the electrocution stopped and the cane didn’t fall. Dave’s question was simple – was I going to be a good girl. He removed the gag and my answer was an emphatic yes.

Dave told me to put on my heels and go get him five bags of popcorn. Without hesitation I found myself in heels and a nighty headed for the office surrounded by rabid rapist. Dave drove up and intercepted me just before I got to the office and we left the drive-in. As we drove I enthusiastically sucked on Dave’s cock, but he had not come by the time we arrived at a nearby gentleman’s club. I was unaware it was a more or less private party as Dave escorted me inside still dressed in a nighty and heels.

On stage a tiny young woman was restrained to a table and being fucked by a cock as long as her forearm. She was ecstatic and after two more studs made deposits inside her Dave told me to clean her up. After hours of such service between my wonderful Mistress’ legs it was a pleasure and a task for which I am eminently qualified. At least a dozen men watched as I licked and she climax over and over.

I couldn’t see her face when they turned her over and I didn’t see how her tiny little butt could accommodate a male organ, but accommodate it did over and over. Cleaning a rectum is neither as tasty or as easy as cleaning a pussy so my host decided to help me. I was tied to a table at center stage with my legs hoisted in the air. My tiny little friend climbed on my chest and began dumping her load into my mouth. Meanwhile, the studs began filling my pussy as they had filled hers.

When I was released I was forced to kneel in a child’s wading pool. Dave walked over and pulled out his cock, but not for me to suck. He pissed all over me. Properly humiliated I was led off stage to a dressing room where my tiny friend joined me. We brushed our teeth and gargled before cleaning ourselves with douches and enemas. We bathed in a large Jacuzzi, washed our hair and played together like two loving lesbians. I was fascinated by her tiny body and kissed every inch. We cuddled, kissed and touched with tender loving care. I despaired I might never see this child of love ever again.

I was dressed in a lull length white silk gown that had long sleeves and a high collar. Low heel white satin slippers with open toes adorned my feet as I returned to the stage. There I was pilloried head and hands, on my knees when Dave appeared dressed only in a black silk robe. This time there were no games. He put his cock in my mouth and began to fuck my face ramming his beautiful cock deep into my throat. This ballet of lust continued until he had climax and fed me his gift of cum. Dave sat in a large chair contented and relaxed as a young man joined us on stage.

To my chagrin he started piercing my ears. A process I had steadfastly resisted because of the obvious conclusions it suggests. He didn’t just pierce them; he put three holes in each ear and filled them with silver studs. Dave was twirling the plunger a reminder not wasted on me as he explained I was to wear hoop earrings as soon as the holes healed and that before future dates I was to go to a beauty parlor for the full treatment. If I didn’t pass as a girl in public, I would spend the night with the plunger in my hand until I did.

Dressed in a short plaid skirt, a pink tank Kurtköy Masaj Salonu top and high heel boots I lay with my head in Dave’s lap as we returned to the Apache. There was no sex in fact there seemed to be a spirit of compassion on his part as he stroked my hair. At least that was my impression until he let me out a couple of miles short of the drive-in and drove off.

I’m accustomed to walking in heels and despite several offers for rides I made it back to the drive-in and home without incident. Once home I relaxed in a scented bubble bath with some Scotch and put some ointment on my wounded butt. It had been a wonderful day and a precursor of things to come on Saturday. I sleep that evening in my long white cotton gown a contented girl that had served her master well.

My butt really hurt the next morning and looked worse, but a nourishing breakfast and a half pot of coffee had me planning my evening. I decided on a trip to Shreveport for shopping and lunch. I wouldn’t be able to use my new piercings for a while, but I wanted some hoops when they were ready. I also wanted something special for my date.

After lunch I bathed, douched and put a tampon in me before donning “Skinny” jeans, a pink and white cowgirl’s shirt and lady’s boots. Underneath I wore pink silk panties and a Kotex for comfort with my cage along with a white cuff top brief and a pink lace camisole. My wedding rings, watch and ID bracelet were my only jewelry other than the studs in my ears and a silver cross encrusted with turquoise around my neck.

The mirror reflected the fact that my unisex days seemed to be coming to an end. With my wife dragging home an endless stream of studs and exposing me to her girlfriends, my life as a male seemed precarious at best. I have no real regrets about my life choices, but I dread trying to explain all this to the kids.

I enjoyed a long stroll along the river, lunch at the Hot Dog Shoppe and ice cream for dessert. I already had a brand new outfit for my date that night, but at one of boutiques I found a navy blue skort with a banded waist and a crop top with puffy sleeves and a square neckline. I couldn’t resist so I bought it. I’d wear white sling-back, open-toe heels and a white shoulder purse. Thor, my date for tonight, would be very pleased with this sheik, uptown look.

I decided to stop at one of the casinos and throw away $20.00, but my luck was running good. A couple of drinks and an hour later I had $37.00. I was so intensely working my machine I didn’t notice a man slip up behind me until his hand rested on my right breast. He played with my nipple jewelry and whispered for me to meet him in the men’s room. Predictably I ended up with his cock in my mouth and a wonderful taste to carry me home.

Back home I just couldn’t get enough of that black inflatable and its two quart intruders. After four I still wasn’t satisfied, but I had to stop because I had to get ready. My body was hairless, my nipples adorned, my clitty caged and my toes polished. My pussy was super sensitized and begging me to remove the cotton cylinder inside me.

I slipped into panties with a Kotex pad, my brief and my adorable new skort. I decided on a white elastic bandeau top to hold my breasts in place under my new crop top. My waist is too big and my hips too small giving me that boyish figure many men find irresistible in a girl.

With heels, jewelry, an anklet and a shoulder purse packed with the essentials I was ready to go. The anklet is special. From a thin silver chain, the following silver block letters hang (C-U-M-S-L-U-T). I packed my portable bar and headed for my rendezvous by the lake.

It was twilight and I was early when I arrived so I found a picnic table and got out. Security guards and offended passersby are always a concern, but like the brazen bitch I so long to be, I lit a thin black cigar and drank a tall Scotch and soda as I waited. I sat on the table with my heels on the bench seat. I had to get a towel from the car to sit on because of the damn ants. As cars passed by it was an enormous thrill. I took out my compact and applied a fresh coat of lip gloss. As I viewed my rich strawberry colored lips in the mirror I thought about the fact they would soon be wrapped around a cock.

Caught in my reverie I didn’t notice Thor drive up. The lights from his truck illuminated my quickly darken surroundings. He walked over put his arms around me and kissed me, his strong tongue probing my mouth. He nuzzled my neck and commented on how good I smelled. I placed my hand on his member and whispered I wanted him.

He told me to bend over the table. I stood, removed my skort, undies and tampon, and then bent over the table with my legs spread. Thor spat on my pussy then pushed his meat inside me. It was marvelous being filled and drilled by that hot cock. I would have gladly remained there all night, but suddenly I jumped – the damn ants were on me.

It broke the spell for Thor and he wasn’t very happy, but he had a quick solution. We would go swimming. I didn’t have a suit, but he did – a sleek black one piece. I was practically naked anyway so I changed right there. He changed into swim trunks in his truck and we walked down to the lake together. On the way he handed me a nose clip and goggles.