Part 7
The following narrative is that of a retired Starfleet commander. Though many of the narrated details did actually occur all names are fictitious and locales and dates are changed to prevent individual identification.
Some of Janet's encounters were strange, without being trials or tribulations. After she lost her job, she tried to get a better percentage from Jerry. He did give her a slightly better cut, but he figured she could do more on her back to gain more for both of them. So it was that she was set up for a Saturday morning assignation.
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I arrived at the address I'd been given just at 0930 hours. A note taped to the front door told me the door was open and to go in and lock the door behind me. Inside I found a girl sitting on a couch. She was fully dressed in a shirtwaist dress but wore a hood covering all of her head except for her mouth and nose. She wore cuffs locked on her wrists chained together at her back. Another note by the couch explained the girl was Annie and for losing a bet she was required first to perform cunnilingus on me and then I was to sodomize her in the ass with a strapon which was on the table with the note. The note explained that the hood blocked Annie's hearing as well as her sight. The cuffs would keep her helpless until somebody returned later in the day.
I thought it was strange to pay someone to come in for the job when whoever cuffed and hooded her could have done it themselves. In any case I was paid for and set about following the instructions. I could enjoy a good pussy licking. I unzipped my skirt, let it down and stepped out of it. I set it on the table, took off my panties and set them on the skirt. I gripped Annie by the shoulders and maneuvered her to lie on her back on the couch. I was able to kneel astride her facing her feet so my pussy was over her mouth. I let myself down and she immediately started tonguing my slit. She managed to force her tongue into my pussy and massaged my pussy lips. I moved back a little and she licked my clit. It felt delightful and I wondered if I might get her to lick pussy more than once. When she started sucking on it I knew I was going to cum.
I thought I would tease her a bit and started unbuttoning her dress. She stopped sucking and acted like she wanted to get up. I persisted and had enough buttons undone to expose her bra. I was surprised to find her bra filled out with breast forms. I had to wonder if it was a man or woman. I reached down and pulled up her skirt. Under her panties I saw a wide belt of chain mesh which appeared it might be a chastity belt of some kind. I was sure I could detect a bulge of a cock.
I resumed my position and the pussy licking started again. It only took a few minutes till I was cumming.
I got up and picked up the strapon. It was still in its package though the side was slit open so I didn't have to struggle with the plastic. I examined it to figure out how to use it. It was made to be used by a female with a probe to fit in a pussy while the main part was a penis shaped probe. I pulled it up my legs fitting the small probe in my pussy and adjusted the straps to secure it on me.
I forced "Annie" over on to her/his stomach and pulled the panties down and off. The chain mesh did not extend through the crotch but joined a pair of belts across the ass cheeks and fastened with small padlocks to a waist belt. It left a clear way to the ass hole. I put some lube on the dong and assumed a position kneeling between his legs. I pushed it in his ass and tried a few strokes. I found a position and rhythm that felt pleasant to my pussy and continued until I was cumming.
I took off the strap on and put my panties and skirt back on. I was ready to leave but I was curious about what was going on. Instead of leaving I went to the door and opened and closed it from inside. I removed my heels since I wasn't positive his hearing was fully blocked.
In a bit he struggled to a sitting position and then stood. In my stocking feet I quietly followed him into the bedroom and watched him fumble his way to a dresser and pick up a set of keys. I easily took the keys away from him. I figured out which key locked his hood on and unlocked it. I pulled the hood up off his head which also took off a wig he had under the hood.
I insisted on him telling me what was going on. Eventually he explained he was a transvestite who wanted to dress as a woman but what he was really into was forced feminization. As his voice was husky I suggested he needed a drink of water. I let him have the keys and he was able to undo his cuffs. He told me he was going to the kitchen for water and asked if I would like anything. I asked for coffee and he replied he could make a pot in just a minute. I followed him to the kitchen and took a seat at the table.
We both had coffee and I questioned him further. He insisted he was absolutely heterosexual. Today's escapade had been his only attempt at having anyone else come in. His ex-wife had appreciated his fetish and had insisted on him dressing in dresses or skirts at all times in the house. She required him to do most of the housework and to service her whenever she wished, usually orally.
I began to see where I might profit from this encounter. My usual weekend housekeeping had suffered from my Friday and Saturday evenings spent whoring for Jerry. If I could get Annie to be my weekend maid it could help me quite a bit.
I told him to fetch my shoes that I had left at the front door. Without a word he got up and not only fetched them but knelt by my chair and fitted them on my feet. I told him to take off his dress. He meekly complied and stripped down to bra, stockings and his chastity belt. I commanded him to kneel in front of me and lick my pussy. He did so pushing up my skirt, taking down my panties and burying his face between my legs. With a little direction from me he licked me to a very satisfying climax.
I told him he was to be at my apartment at 0930 hours the next morning. He could wear normal male clothing to get there but was to be wearing his chastity belt locked on while leaving the keys at home. He was to bring a complete set of female clothing to change into after he arrived as well as his wrist cuffs. I would have sufficient housework for him to serve as my maid. I figured I would also have him licking pussy whenever I wanted.
I left him reminding him to be there at 0930. I went home, had a bubble bath and rested for the afternoon disregarding the housework that needed doing. Jerry took me to the motel that evening and I went through the usual routines, several missionary screws, a few blowjobs and a couple of doggie styles. I usually felt doggie style was demeaning for having me kneel on the bed, legs spread showing off my pussy, head down and my ass up in the air. That night I had a customer who screwed me so slowly that I really enjoyed the feel of his cock stuffing my pussy full. I had such a good orgasm from it plus a second lesser one that it left me with an afterglow for most of the rest of the night.
The next morning Annie showed right at 0930 hours. He was able to enter the building since the computer knew him from the picture I had taken with my communicator. I had only been up a short while just long enough to start coffee. I pulled on a robe over my nightgown and let him in. I led him into the bedroom and told him to change his clothes. He stripped completely naked except for his chastity belt. I watched as he dressed in his feminine clothes. It was a bit weird to watch him roll stockings up his legs and attach them to his garter belt and then pull up a pair of panties. He put on a bra and filled it with breast forms. I asked if he had brought a wig. He had and I told him to put it on.
I went and laid on the bed and told him to join me. He crawled between my legs and pushed up my nightgown. I enjoyed his tongue licking the lips of my pussy for a while and then told him to put his fingers in me. He did so and then concentrated on my clit, tonguing and gently nibbling on it. When he sucked it in his mouth and passed his tongue back and forth on it my orgasm started. I raised my legs gripping his head between my thighs while the waves of pleasure surged through me. It took me a minute to realize he was in distress and relax my legs to release him.
I told him to finish dressing and went to the kitchen for my coffee. When he joined me he had dressed in a dark knee length skirt and a white ruffled blouse. His makeup was well done and he could have passed as a female as long as nobody got too close. I was having only toast but asked if he wanted breakfast. He accepted coffee but declined anything more explaining he'd already had breakfast. We talked for a bit over coffee and I got some explanations concerning cross dressing. After coffee I set him to vacuum and dust the bedroom and the sitting room and clean up the kitchen while I had a relaxing bubble bath.
After my bath I put on a robe and did a quick check through the rooms I'd told him to clean up. He had done very well and had even put away most of the dishes from the dishwasher. A few things were left out and I had to instruct him where they were to be put up. I complimented him for doing a good job and then had him follow me to the sitting room. I took a seat in my recliner, spread my robe open, spread my legs and told him to go down on me.
I told him to spread my pussy lips and push his tongue in as far as he could. Then I had him leave his tongue in me while he took off his top. I was delighted at how his tongue shifted as he went through unbuttoning his blouse and pulling it off his arms. I enjoyed the sight of her hair brushing my thighs and her back bare but for her bra as well as the feel of her hair against my legs. It was a bit weird but I was thinking of Annie in terms of she and her. She pushed her fingers in my pussy and started licking my clit. I could feel an orgasm building. I raised my legs up over her shoulders and it intensified the thrill I felt. My orgasm was a spectacular eruption coursing out from my pussy and enveloping me from head to toe. She continued teasing about my clit and my pussy continued sending thrilling waves of pleasure through me. As it subsided a little I was ready for her to stop but I was too befuddled to tell her to stop and too weak to move. Eventually I was able to push her head away but had to rest a few minutes before I recovered.
I told her I enjoyed it and I thought I would be glad to have her serve as my maid and slave every Sunday.
She simply answered,"Thank you ma'am."
I instructed her to clean up the bathroom. She got up and picked up her top but I told her to leave it off. I suspected as a cross dresser she enjoyed light humiliation and could enjoy being kept with her bra exposed. She readily obeyed and went off to the bathroom half dressed. I definitely was going to insist on her return. She not only served as a maid allowing me to be lazy but provided the ready thrill of worshipping between my legs.
I set the recliner down and had a nap. When I woke Annie had finished in the bathroom and was sitting on the couch. I had her fix a light lunch for the both of us and we sat in the kitchen eating while I questioned her about likes and dislikes. After lunch I returned to my recliner.
I asked if she had brought her hood and cuffs. I had her put them on while she stood beside my chair. I unzipped her skirt letting it fall around her ankles. I kept her standing there helpless in her underwear while I read a magazine. I enjoyed teasing her every so often brushing a hand over her pantied ass or her stockings. It sometimes caused her to shiver and I found I enjoyed teasing her. Through the afternoon I enjoyed a couple more lickings.
Eventually I had to let her get dressed and return home. But I had her promise to return the next Sunday early enough to serve me coffee in bed. I looked forward to a long relationship with Annie as my slave/maid.
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That had been a bit of a different twist on Janet's life. Annie did return and willingly served Janet almost every Sunday. For myself I felt Janet deserved any deviation from her life as a slave/prostitute.
11.08.12
story continues in An Ensign's Fantasies 8
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