Young Times Pt V
Movement at the end of the hall jarred me from my trance and brought me back to the future. Someone had come into the arcade and was making the circuitous route toward my little corner. I catch sight of him as he rounds the corner coming straight at me. I recognize the face and estimate I've been with him a half dozen times maybe. I remember him as an OK guy with a pleasant personality and what I suspected to be a slight bisex streak. My kind of guy, in other words.
He goes into a booth three up from where I'm standing, giving me the eye before he closes the door. So I ease up the aisle until I'm directly in front of it and begin the waiting game. Some times it's like this, a game, and I don't know why men play it out like this unless they need video time to get it up. Whatever. I light a cigarette and take a deep drag, holding the smoke in my lungs for the longest time, and when I exhale, the door cracks open just enough for me to see inside. And what I see makes me thirsty and hot, he's sitting on the bench, facing forward with his cock in his hand, already glistening from the attention. I move to the door, dropping my cigarette on the floor and crushing it out under my sandal as I push lightly on the door and it swings open.
I quickly slip into the booth, my eyes glued to that delightful dick in his hand.
`Mind if I watch with you?' I ask. It's the epitome of rhetorical questions. I know very well how this ABS business works, I've been a regular in the booths since they opened the first one twenty odd years ago, and probably will be til the day I die. Nowhere else have I found such a steady supply of horny men. It was almost too easy, but I'll take easy every time.
`Not unless you've got eyes in the back of your head' he joked.
`Not to worry baby, I'll devote all my attention to what goes in my mouth', I promise, and with that I drop to my knees and grasp his cock in my left hand, replacing his, and slowly jacking him from base to tip. He hardens and lengthens in my hand, and without wasting another second, I drop my head as my mouth comes open and engulfs the head. I pause there as I take in both the smell and the taste. All man.
`Ahhhh...baby, that's hot...', he exclaims as I take more of him inside my mouth. He has at least 7 inches and in no time I have the head past my gag reflex and into my throat. I back off an inch or two and take it all down again, holding tight to the base of the shaft so that I still have an inch or two to play with. And play I do, tightening my throat around the head to massage it as I use my tongue to massage the bottom of the shaft.
I am good at this. In fact I am an excellent cock sucker, and I enjoy using my talents to make men feel good. And they feed my ego by complimenting me on my skills, so I do everything I can to earn those compliments. That's one thing I had come to realize 30 years ago – I came to treasure those compliments because they reinforced not only my ego but also my sense of worth.
But it's not about the compliments this morning. I had received all the compliments I needed last night – `great looking bitch, nice ass, super cocksucker, fantastic fuck' – and I had heard that a lot. No, this morning is about physical satisfaction, I need to get off, and if I have to suck a few dicks in the process, well, I'm more than OK with that.
`Oohhhhh God that's so fucking hot..' my companion whispers.
`You want a piece of ass baby' I ask, hoping the tone of my voice doesn't give away my desperation.
Ahhh, nah' he replies I don't want to work this morning honey. Just keep that hot mouth working on my cock and I'll give ya a big juicy reward.'
OK baby, I'll do ya good. Give me your cum.' I guess that I'm going to have to settle for what I can get from this guy. Ya mind if I get off while I'm doing it?'
`Nah babe, that's OK, do what you have to, just don't go spittin or nuthin'.
`Don't worry lover, I always swallow' I promise.
I'm on my knees, and as my mouth goes back to his cock, I spread my legs and fish my dick out of the thong that had been confining it in a tight tuck. It's limp, but I know that with just the right amount of attention it will harden and I can beat off. So I start massaging and pulling on it with my right hand as my left rests on his right leg to steady me.
But before I have a chance to get very far, I feel the tell tale signs of his climax building as the veins in his cock swell.
`Oooh...shit...ooooh...I'm...ooooohhhhhh!' he exclaims as I feel the first spurt hit the back of my throat. I pull out a bit so that the entire head is in my mouth as it spurts wildly. I time my swallowing just right, not letting my mouth fill completely before gulping it down, then letting it fill to the same point. As proud of my cock sucking skills as I am, I'm equally proud of the fact that I have perfected the art of swallowing to the point that I never, ever, waste one drop of the pearly liquid. I can keep up with the most prolific cummers!
And this one is prolific, I count 4 separate mouthfuls before the flow tapers off and I have a chance to savor the taste he had left in my mouth. Strong and tart, one of my favorite flavors, and I suck and lick until there is no more in him or on him. Then I lick my lips and take in what little had oozed out around the `O' my lips had formed around his cock.
There' I say all empty and all clean. And all in my stomach, just like I promised.'
You're the best baby' he compliments, as he stands to go. Watch the movie on me' and he leaves a token on the seat next to him.
Thanks baby' I reply and thanks for the good time. See you later?'
`Yeah, see ya round', he promises as he slips out the door and closes it.
And with that I get off my knees and sit on the bench. I put the token in the slot and dial up a shemale movie as I tug gently on my still only half hard dick.
As I sit there my mind wanders back again to those early years...
Young Times (the between years) Part V
My second night as a TV hooker promised to go a little easier than had my first for two reasons. First, it was the second night and therefore I had some idea of where I was going, what was expected of me, and what I could expect. And the second reason was because I thought I would be treated better by Mandy and her friend, my fellow hookers from the night before.
And I was right, Mandy welcomed me with, if not enthusiasm at having competition for the scant business that went down, then at least a begrudging acceptance of the fact that I was there and would be there to stay until Bill said I wasn't. I think Mandy resented me because of my looks and my whiteness' but in the end was so afraid of Bill and Cookie that she made friendly' and protective', telling Bill several times before he left I take ker huh, fo sho.', which may or may not have influenced him. But at least he was civil to her, while letting her know that if anything bad happened to me, no matter who did it, that she would answer to Bill.
Street hookers may or may not form bonds, but one thing they do is trade experiences. It can be a long time between johns, and no matter how you may have seen us strut and pose, when there are no johns around we tend to pass the idle time the way other girls do – we bitch, we gossip, and we share our life's story with any kindred spirit willing to pay us attention.
And this evening the traffic was non existent when I go there. Both Mandy and the white girl named Cupcake were on the corner, smoking and talking. After a little idle chit chat the conversation turned to how we each ended up on this street corner, and I received my first glimpse into the world of transvestism, transgender, and transexualism. Over the course of the next two weeks I would learn more about these two `girls' than I knew about most anyone. Although this information came to me in bits and pieces, I've summarized it for the reader in this chapter.
Mandy started dressing' around the age of eight, first just innocent make believe role playing around the house. After that phase quickly ran it's course her hobby' progessed to the actual wearing of girls clothes, first a few things of her mother's and then actually stealing girls underwear from several clotheslines in her neighborhood. Her mother caught her in her room one day, dressed, and punished her by making her keep the clothes on til she went to bed that night. Instead of the humiliation her mother expected from this punishment', Mandy was overjoyed by this, her first dip into the pool of transvestism. And rather than curing' her as her mother planned, the experience convinced her that she needed more of it. By the time she was in middle school, her mother had given up all attempts to convince her otherwise, completely ambivalent about how her son dressed around the house.
It was puberty that shattered her mother's ability to deal with the situation. Like most boys, puberty had the effect of turning our world upside down and bringing out desires we had no idea were in there. Mandy was outed when he let those desires overrun what little discretion a boy at that age has. The resulting incidents all caused an uproar at school and, eventually, at home. His mother's pendulum swung to far travel the other way and she cracked down on Mandy like a prison warden.
Of course that didn't help the situation and Mandy ran away, at age 15, to the dark secret street life of SE Roanoke. `Living' in an abandoned warehouse with an odd assortment of homeless men and women and working the streets for enough money to survive, he hooked up with a kind older gentleman who took him in. Mandy became a virtual slave to this guy, cooking, cleaning, ironing for him in exchange for the security of a real home, complete with a place to sleep and three square meals a day. But, even with this security, Mandy wasn't complete. The desire to dress as a girl pervaded everything she did, and her benefactor made it perfectly clear that her dressing was not part of the deal. He politely corrected her once, and then threw her out when he came home one day and found her dressed for the second time.
After a few nights on the street, Mandy crawled back to her mother, her last resort really, and promised to live a celibate, `normal', albeit TV lifestyle in exchange for her old bedroom back. That strained relationship had worked for almost five years now, with Mandy's home life completely separate from the street and sex life. Her mother knew, of course, that Mandy was hooking, but as long as she didn't bring it home, everything stayed on a more or less even keel and they co existed amicably.
Cupcake, the white tranny, was a different story. He, she, had been introduced to dressing by way of an affair with the boyfriend of her mother, who hosted a series of boyfriends after Cupcake's father left. When she was 14, the then resident boyfriend had befriended Cupcake in an overly sexual father-son way, cumulating in the boy's first MTM sexual experience, completely consensual. So consensual, in fact, that the next day Cupcake became the pursuer, initiating the sex. The mother worked an evening shift, the boyfriend a midnight shift, so after school trysts were the order of the day.
It was the boyfriend who encouraged Cupcake to dress, complimenting her on her looks and body. Borrowing panties, bra, and a slip from her mother's chest of drawers, Cupcake modeled and pranced around the house to the boyfriends oohs' and ahhs' until they were both so hot that they had sex in the floor and finished with Cupcake bent over the kitchen table, with the panties around her ankles, and the boyfriend pounding her, taking her anal cherry and any innocence she had left.
Those few weeks of afternoon delight convinced Cupcake that she was a girl in a boys body, but it made no difference as long as she had a man to love her and treat her like the girl she was becoming. Gone were any fears or thoughts that what she was doing was wrong, replaced by the sense of right she felt in her newfound feminine role. Gone were any second thoughts about what path she was taking, her mind now filled with what and who she wanted to be. Born, was `Cupcake', a nickname bestowed upon her new being by the boyfriend.
This idyllic arrangement was shattered when Cupcake's mother came home early from work one evening and discovered the two lovers `in flagrante delicto' , the boyfriends cock in Cupcake's mouth. The shit hit the fan with a sickening thud!
Cupcake was on the street that evening, finding a brief respite in one of the homeless shelters until they discovered her age and turned her over to child services, who tried to return her home only to be turned away by her mother. With no other option at this point, she was returned to the care of the homeless shelter for the night with the intent of finding temporary foster care, while instituting legal proceedings against the mother.
Presented with a judge's order, the mother capitulated and let Cupcake come home, while kicking the boyfriend's ass out on the street. In my mind, the right kind of justice was done there.
The mother laid down strict rules about dressing and behavior, and faced with no alternative that she could think of, Cupcake complied,. She put up with living a life not hers both at home and school for the next two years before meeting the boy who would eventually become the love of her life. They carried on a clandestine affair after school at his home where Cupcake could finally dress as a girl again. After two years of this relief, they both graduated high school and Cupcake left home for good, accepted at the homeless shelter now that she was of legal age.
Life in the shelter was not the answer for a transvestite and Cupcake was beat up several times after being exposed. She was beaten and raped on what became her last night there. Her boyfriend moved out of his parent's house the next day and the two found an apartment in one of the low rent sections of SE Roanoke that same day.
Within a week of paying the first month's rent and security deposit they were broke. The boyfriend found work as a dishwasher for a local restaurant, but that only covered a portion of their expenses. After a long discussion of finances and the need for money, Cupcake hit the streets as a tranny hooker. They had been breaking even financially for the past two years, and their romance was intact, in fact the lack of money problems had brought them closer together as they depended on each other even more than before.
When it was my turn I filled them in on the details of my young life, from my first homosexual encounter with the two old guys in the boarding house, my flowering (and deflowering) at band camp, being outed all those times at school, being prostituted out by my high school teacher, and finally my running away from home and `working' for Clarence and then Bill. I think they were surprised, and a little impressed, at how experienced a seventeen year old from a small town could be.
And, they found it hard to believe that this was only my second night dressing as a girl. According to them I didn't resemble a tranny as much as I looked like a real life girl. I guess life on the street was hard on trannies and I still had the youth and looks of someone who hasn't been exposed to the wear and tear of prostitution, although I had probably had as many, if not more, sexual encounters than either of them.
An obvious truth, the beginning of an understanding, began to settle in my mind – both Mandy and Cupcake had discovered their feminine leanings before they reached puberty, so when their hormones went wild on them they had focused not on homosexual relationships per se, but rather saw themselves as feminine and the relationships more normal male-female. Both had found men willing to view the sex more or less the same , with crossdressing the acceptable passive role, again normal male-female, and those encounters tended to reinforce, in a strange way, their sense of self worth. I, on the other hand, had discovered my fondness for cock before puberty, and by the time my hormones took off, I already identified myself as a queer. And the boys and men I had sex with identified me as a queer, first in class, then school, then as my reputation grew, as the town queer. I would soon come to realize that my taste, my behavior, my whole demeanor straddled a very fine dividing line between homosexual and what today is know as transsexual. But in my small town, and my meager knowledge of the gray areas of human sexuality, you were either straight, or queer. Transexual was not a choice in small town Virginia in 1982.
Both Virginia and I had some growing to do before we came to terms with each other. And on that, my second night on the street as a tranny, I was preparing to outpace Virginia in coming to, and accepting, those terms.
To be continued... leslitv@gmail.com