This is a true story; If you are not 21 or over do not go any further. If you do not like man on man sex go no further.
Learning to Please - Part 7
Howard and I did not go out for dinner - I wasn't ready to merge my real life outside with this fantasy world we had. I felt weird, confused and wanted to leave. I hurried to leave explaining that I had tests to study for, but that I would call him. My ass was sore and the train ride back to college seemed particularly bumpy. As I sat there, I recalled everything we had done, and thinking about it made me feel very horny. I looked at dozens of men going about their commute with blank, dull faces, their minds elsewhere. Inside I was glowing with the thought that I had literally gotten down on my hands and knees and gave a man my mouth and ass - I gave a man sexual relief and he thanked me for it. Part of me wanted to turn right around and ask Howard if I could sleep over. Part of me thought that would be pathetic and I had better get control of myself.
I spoke with Howard a few times over the next few weeks. I had had a great time with Howard, but was becoming nervous. Nervous about what I was becoming. Nervous about getting found out. I questioned if this was who I really was - was this something I wanted to become?
I continued with my assplay and submissive fantasies while masturbating. But afterwards sometime I'd feel relieved and relaxed, and other times guilty and embarrassed. I buried myself in my classwork and forced myself to have a few non-committal phone calls with Howard.
I think Howard sensed that things were changing between us and it became awkward. Howard said he picked up some new things for me to wear and that he was anxious to see them on me. I gave in one day and agreed to meet Howard at his apartment Friday around 7 o'clock and make a fun night of it. Howard told me that he'd be working late, so that he'd leave the key to his apartment with the doorman for me to pickup. He said, that way I could let myself in anytime and dress and get ready for him to arrive. It sounded fun and I was quite a bit aroused with the thought of getting to his apartment early and dressing up for him, and just walking around his apartment waiting for him to come home and have sex with me.
After my last class, around 2pm I started taking the train to Howard's apartment. When I arrived I spoke with the doorman, giving him the same false name I had given Howard when we met. He asked if I had ID, and I told him, sorry, but I forgot my wallet. He seemed a little doubtful, so I suggested that he could call Howard at work. He handed over the key with a shrug and I took the elevator up.
Once I entered the apartment I locked the door behind me and took a cursory walk through the apartment. It was clean and neat, and Howard wasn't home yet. In the guest room, my room, I found a shopping bag with a few packages in it laid out on the bed, and a card.
I opened the card to read:
"Dear Christine,
I'm glad you were able to make it over to spend time with me tonight - it will be a lot of fun. You'll find a few new items here for you to wear, which I hope you like. I'll be home promptly at 7 and I would really love it if you greeted me at the door with a freshly made martini.
Thank You - hugs and kisses (on your bottom),
P.S. You'll find a new wig I picked out for you on the vanity in your bathroom, I hope you like it because I think it will look hot on you.
Howard"
Christine - my new name, his choice for me. I walked over to the bathroom and looked in at it, sitting on a Styrofoam head-shape. It was a medium length, curly hair style wig in medium chestnut. I reached out to touch it and run my fingers through it. It felt a little plasticy, but it was very sexy looking and I knew it looked better than my current hair style. I found the box in a shopping bag on the floor (it cost $85!) and read the instructions for care and use. I ran the bath and went back into the bedroom, undressed and folded my clothes and placed the neat pile in one of the empty dresser drawers.
I looked at the bag on the bed but decided that I had plenty of time to go through the packages, and that first wanted to soak and relax. I wanted a drink, so I put on a short pink satin robe that was hanging in the bathroom and started for the kitchen. I stopped at the doorway, paused and walked over to the closet and found my box of high heel shoes. I slipped them on and looked down at my long, thin legs - glad that I had decided to keep them shaved. I had even shaved most of the hair and peach fuzz off of the rest of my body. All that remained, aside from the hair on my head, was my underarm hair, and a small patch at the top of my pubic area. Although I had taken the time to carefully shave the light hairs from my scrotum, ass-cheeks and underneath, I liked to keep this small patch of hair at the top of my pubic area, which I liked to run my fingers through.
Sitting on the bed I crossed and uncrossed my legs, looking down at my feet and admiring how nice my legs looked in the open toed shoes. I opened my robe to observe that, although my small nuts seemed to tingle with anticipation, my small cock had shrunken to it's smallest, softest, form - almost as if it had moved back into my body. I went through my dresser drawers to find a pair of panties and slipped them on.
Remembering the bath, I carefully walked back to the bathroom and turned of the water. The bubbles were piled high and the water was very hot. Now for that drink. With the robe hanging open I walked to the kitchen - slowly, getting used to the heels - and took mental inventory of the refrigerator contents. No champagne. Darn it!
I walked over to a piece of furniture my family referred to as a 'tea cart', which I expected to hold bottles of liquor. I was right. I took inventory of the contents and was glad to find a small book with drink recipes. I found the ingredients for the martini and set them aside. With the bottle of vodka in hand I went back into the kitchen and fixed myself a nice tall vodka and orange juice, and gulped half of it down, and then refilled it.
Drink in hand I wandered through the apartment, trailing my hand along the furniture and the walls, somehow wanting to touch and not be afraid, not like a visitor to a museum, but like this was a place where I was welcome. I stood outside Howard's bedroom, leaning on the doorway looking in. Before I came over today I had already decided that I wouldn't snoop through Howard's things. He was trusting me by making the key available to me and I didn't want to break that trust. The room was neat and the bed was made, but some of the dresser drawers were partially opened, as were the closets. From the hallway I could see into his master-bath and see that towels were hanging and the vanity was covered in his grooming products. I reached down and pushed my small nuts back between my legs as far as I could and crossed my legs tightly to hide as much of my boyhood as possible. I imagined standing there and posing for Howard, and him looking at me with lust and need, like he had the last time we were together.
As I stood there my left hand came up and cupped my small, flat right breast. I sipped my drink as I touched and teased my breast and nipple. I was transfixed staring at Howard's bed, wondering if he'd make love to me in his room tonight. I didn't want to think about it, but with jealousy I wondered about how many other women or boys he had enjoyed in his apartment. I started to fantasize about standing there watching him from the doorway as he thrust his cock into another woman, the woman arching her back under him, her heavily lacquered nails digging into his shoulders and back. I imagined them hugging afterwards and laughing. As he rolled off of her, I'd see her propped up on her elbows, legs apart with Howard's cum oozing from her. With a friendly grin she makes a slight nod of her head, inviting me to come over, and as I approach she spreads legs a little wider and playfully asks if I 'want some?'. As they both watch me, I carefully crawl onto the bed and place my face into her lap, extending my tongue, and taste both of them. She purrs warmly as I clean her, and then switches to a mocking tone, telling Howard, 'Ohhh, she is good Howard!'
I closed my eyes and tried to clear the scene from my mind, and took another long sip of my drink. I left Howard's room and went back to my bathroom, stripped and sank into the tub. I soaked and relaxed until the water was cool. I rewarmed the tub and finished washing, paying special attention to my bottom.
I dried off and put the robe back on, anxious to see how I looked with the wig on. I felt a little nervous as I lifted the wig from the mannequin head and felt it in my hands. I looked at myself in the mirror trying to raise the courage to put it on. I searched through the vanity to find the lipstick I had used before and put it on. It took a few attempts again, but finally I had attractive lips. I scooped up the wig, closed my eyes and bent over and flipped it onto my head. Keeping my eyes closed, I turned my back to the mirror and tugged and adjusted the hairline until it felt right, and felt sure that none of my hair needed to be ticked in.
I slowly turned around to see how I looked. My heart skipped a beat - I looked feminine and...beautiful. I immediately saw areas for improvement - my eyebrows, perhaps some colored eye shadow, but I smiled at myself and was quite happy. I looked cute, hot, and knew Howard would be happy with his selection.
I went into the bedroom to look through the packages Howard had brought for me. The Neiman Marcus shopping bag held several gift boxes of different sizes. The first box held a neatly folded silk blouse, which I laid out on the bed. It was light pink, and the tag told me it was a "Petal Sleeve Cowl Neck" top. I remember gasping when I saw the price tag showing that it cost more than $200. It was beautiful and the cowl neck seemed like it would plunge quite low on me. I liked it. Also in the box was a very thin silver metallic belt, which I imagined was supposed to be worn over the blouse at the hips, event though there were no belt-loops on the blouse. The belt (more like a fine chain) was very long and I guessed the style was meant to be left with a long piece hanging.
The next box was a shock - a pair of long, tight black disco pants in a shiny material. My heart raced as I imagined myself wiggling into them and looking like Olivia Newton John did in Grease!
A smaller box held a pair a black panties, a note card and a small sealed package. The note was from Howard, telling me that he thought I'd look very sexy in the tight pants, but that I would probably feel more comfortable if I lined my panties with a woman's pad. I quickly realized that this might help smooth out any unsightly bulge my boyhood might made. That was very thoughtful of him and I was anxious to try it and see how it looked.
The note had a postscript:
"P.S. - I did my best with the shopping for you, but there is one last item I'd like your help with if you have time. I'd love to see some nail polish on you, but didn't know what color you would like best. Would you be a doll and take a quick trip to the drug store on the corner and pick something out to try? I've left money on the coffee table for you"
My heart was racing again...it seemed so sexy, going to a store to buy nail polish to paint myself for my man...wearing this absolutely hot, slinky outfit, that gorgeous wig...sitting here waiting for 'my man' to come home....
I was in such a hurry to leave I almost forgot the last box. A shoe box - my size. I ripped the lid off to see an outrageous pair of high heeled stilettos with a cheetah print. The outer material was velvet and the foot-bed was a tan padded suede. I actually felt my small cock twitch as I ran my fingers along them. He was going to have me dolled up like a young, thin, Peg Bundy. He was probably going to insist on me wearing the shoes to bed, or maybe even take me standing up in them...
I was flushed and feeling dizzy.
End Part 7