Oscar Night by Jennifer Brock At last year’s Oscar’s, novelist/screenwriter David Fine wore a special dark red tuxedo designed for him by his friend Claude Marsh. After being insulted by TV personality Jane Waters, he joked that if he was nominated again he’d wear a gown. Claude organized a “cabal” of experts to work toward convincing David that the best way to pull it off would be to become as female as possible, and he agreed, especially when his girlfriend fashion model Maritza Delgado was keen on the idea. He even got a number of surgeries to make him more female, and has been working under the tutelage of feminine behavior expert Kay Thomas. When we left off, our heroine Dee had gone on a date with Joe, a paid escort, and was kissing him on her doorstep, unsure whether to send him home or invite him in...

Part 19
Joe was an excellent kisser. Dee didn’t want it to have to stop so suddenly. Maybe she’d had a few too many glasses of wine, or maybe she was just really getting into her role as a woman on a date. When she pulled her face away from his and broke the kiss, she still kept one hand on him while the other got her keys from her purse. She threw caution to the wind. “Would you like to come inside, for a cup of coffee or something?”

Joe smiled at her. “I’d love to.”

She opened the door and led him to the living room. “Take a seat.” She gestured toward the furniture.

She started to head toward the kitchen to start the coffee pot, but he grabbed her arm. “That can wait. You’ve been on your feet all night, and deserve a little time off of them.” He kept his right hand on her back, and did a quick move that caught her in the back of her knees with his left, and he scooped her up effortlessly, as though she were petite and lightweight. She let out a squeal of surprise and threw her arm around his shoulders to balance. Dee wondered what he was going to do. Was he planning to carry her upstairs and have his way with her, like some conquering barbarian?

That didn’t seem to be his plan, which left Dee feeling almost disappointed. He looked around the room for a moment, and then sat down on the couch, keeping her across his lap. He reached over and slipped off her shoes. “These make your legs sexy, but I’m sure your feet are killing you, especially after all that dancing.”

His strong fingers started kneading the ball of her left foot, and it was only when he made her feel so good that she realized how much her feet really had been hurting. Dee let out a tiny moan of pleasure, and almost couldn’t keep her voice in the feminine register. “Ooh, that’s good! Keep it up and I will be your slave forever.” She writhed a bit and flexed her toes. He shifted and got his other hand in on the action, allowing him to devote his attention to both of her feet.

Dee was in absolute heaven. Joe was a well-trained expert who definitely knew his way around a female foot. He even slid his hands up and massaged her aching calves. This was better than sex! She wiggled some more, not realizing exactly the extent to which she was grinding her enhanced posterior against his lap. When it got to be almost more than she could take, Dee sat up and wrapped her arms around his neck, pulling his face toward hers for a kiss. She welcomed his tongue into her mouth and hungrily ran her own along it.

Joe let go of her feet and moved his hands around so he was holding her. His kisses were just wet enough without being too sloppy. Dee was so caught up in the intensity that she didn’t notice what his hands were doing until she felt his fingers on her right breast, directly touching her nipple and not just groping her through her clothes. He had deftly unzipped her dress and unhooked her bra one handed while she was distracted, and his other hand seized the opportunity once access was no longer obstructed.

Her first reaction to his touch on her nipple was surprise, and she inhaled sharply, sucking on his tongue. Her second reaction was to twist her waist so her torso was facing him, so he could get his other hand in on the action. She had two breasts, and they both wanted attention. She lowered her shoulders and arched her back to show them off as much as possible.

This chick had some of the best tits Joe had ever seen, and you don’t expect that in a tranny. He grabbed one in each hand — he had big hands, but she had to packing D cups because there was more than a handful, but they didn’t look too big on her. Girls like D don’t grow them that big on hormones alone, so there had to be some kind of implants, but squeezing them felt real enough to Joe. Her nipples were somewhat on the small side, but considering that she used to be a dude they were fine. And they were very responsive, which made up for it. They stood up as soon as he brushed his fingers passed them, and all the little bumps on her areolas followed. Those little bumps were almost more fun to play with than the actual nipple.

Almost. He rolled each nipple between his thumb and forefinger, and gave each a little twist before letting go. Then he switched to just brushing his fingers across them, drawing a five-pointed star, so he’d hit a different part of the nipple every time and it wouldn’t get over stimulated. He went faster and faster, until he worried he was rubbing her raw and he had to stop kissing for a moment to lick his fingers.

Dee couldn’t remember the last time she’d felt so incredible! She felt as though he was about to give her an orgasm through nipple stimulation alone. She let her own hands wander a little along his chest, tracing the contours of his powerful muscles. She fiddled with a couple of his buttons and was pleased that unlike David’s usual style he didn’t wear an undershirt. His luscious pecs were right there for her to play with.

When his moistened fingers sent her into pure ecstasy, Dee’s breath grew more rapid and she felt her body trembling all over. She had to stop her kisses and just relaxed and let him push her back so he could lower his mouth to suck at her breast. His tongue drove her wild, and when he capped it off by almost biting her nipple it was perfect! And then he moved and did it again on her other breast. She was overwhelmed.

Somewhere in there, her mind caught up with her emotions and she started to seriously think about what was happening. This was fun and all, but there was a line she wasn’t sure she wanted to cross. Joe wasn’t her boyfriend or anything; he was just a guy who’d been hired to show her what a date with a man would be like, and she found out that it was pretty good. But she was in love with someone, and that wasn’t Joe. Would it be a betrayal of that love to let things get more physical?

At the same time, she didn’t want to be a tease. It wouldn’t be fair to Joe to just lead him on and kick him out into the cold, especially after all the wonderful sensations he’d given her. Maybe if she did something for him in return, she’d be able to send him home without feeling guilty about it.

She pulled his face back up to hers and kissed him again, and then she swung her legs around so she was sitting next to him on the couch instead of on top. He seemed a little confused, so she quickly placed her hand on his lap to let him know what she was doing. She figured out how to undo his belt buckle and unzipped and unbuckled his pants. He was already really turned on, so his erection popped out pretty much as soon as she opened the fly in his shorts.

There it was, as real as life, an actual penis, right at her fingertips. She’d never touched another man’s penis before. No, that was the wrong thought. She was a woman, not a man. She didn’t have one of those; that would be ridiculous. She tentatively reached out and lightly ran her hand down its length, petting it as though it were a kitten. It flexed and jumped at her touch. She stroked it again, less gently but more slowly. She could do this. She grabbed the base with her left hand to hold it in place, and wrapped her right hand around the shaft and started moving it up and down, slowly at first, but then gaining in speed.

She saw a little glimmer of liquid at the tip, and the sudden realization hit her that this was going to make a mess. She should have fetched a tissue or a towel or something to catch his juices, but she hadn’t thought things through. It would be just rude if she made him wet his pants, and she really didn’t want to get a new stain on her couch. Her dress was half off, so she might have been able to take it off and use it to catch any spills, but she wasn’t sure if it was dry clean only, and didn’t want to have to face a cleaner and have to ask about bodily fluid stains.

There was only one solution that presented itself to her mind. She was frightened and excited at the same time about it, but she couldn’t come up with a better plan. She slid down onto the floor and knelt between his legs. He got the idea of what she was doing and spread his knees wider to help her out. She leaned in and brought her mouth down onto him, being careful to keep her teeth away.

Dee’s thought had been that she’d continue to use her hands to stimulate him, and only use her mouth to catch whatever came out, but Joe didn’t know that. As soon as she’d brought her mouth into position, he put his hands on the back of her head and held it in place. He rocked his hips and she had no choice but to let him deeper into her mouth. With each thrust, he seemed to increase the pressure on his hands and pushed her head down closer. He even tried to give her encouragement by whispering, “Oh yeah, Baby, you’re doing great!”

Before long, she was taking his entire length into her mouth, fighting back her gag reflex. She did her best to try to use her lips and tongue on his most sensitive areas, hoping to bring him to completion sooner. She caught up with his rhythm, and figured out how to breathe without choking. When his thrusts increased their speed, she even began to bob her head in time with him, without his needing to push her to do it.

After a while her jaw was getting tired, and she really regretted joking about his stamina earlier. He really did have serious lasting power! Fortunately, right around then he said to her, “Okay, Baby. Are you ready?” She really didn’t have time to answer, even if she could have with her mouth full. The thing in her mouth exploded, and she tried to just hold the spurting head in her mouth, but he was still pushing into her.

He softened, and the firm hands holding her head in place became gentle fingers sweetly stroking her hair. “You were amazing, Baby! Give me a few minutes to recover and we can go do something that will feel just as good for you as it will for me.”

Dee swallowed hard, trying not to think about the taste in her mouth. She lightly gave his penis a kiss as she put it away, and her mind began to race. She stood up and nervously tried to straighten the straps on her dress. “I’ve got to go, um, freshen up. Wait right here.” She grabbed her purse and ran out of the room and up the stairs, making sure to keep a sexy wiggle in her hips.

The first thing she did when she got to her room was take her dress the rest of the way off. Her bra had fallen down inside it at around waist level, and it was really bothering her. The second thing she did was to go into her bathroom and brush her teeth three times and rinse out with mouthwash twice. It wasn’t that it tasted bad; she just didn’t want to be reminded of what she’d done. Once her mouth had become kissably fresh again, she was ready to figure out what to do next. She sat at her vanity table and did repairs to her makeup and hairstyle while she tried to make a decision.

There was just no getting around the full extent of what she’d done. She’d had sex with Joe. Granted, it was oral sex, but unlike certain ex-presidents as far as Dee was concerned oral sex was sex. Joe’s penis had been inside her body, and that wasn’t something she could take back. She felt like she’d betrayed Maritza’s trust, even though she’d been given permission to experiment and her Valentine letter had been fairly explicit about what she expected Dee to do with some man.

But at the same time, she didn’t really regret having sex with Joe. She’d been curious about how it felt to be a woman with a man, and he’d shown her some of that. It had been especially exciting for her when he’d taken control and almost forced her to do what he wanted. That’s not to say she’d enjoy being literally forced; rape wasn’t fun for anyone. But it was a thrill for her to be able to just submit completely and follow his lead. The idea of surrendering all of herself to him completely was very tempting.

Since she considered that she’d already had sex with Joe, what would be the harm in having more sex, in a more intimate manner, allowing herself to be as complete a woman as possible? She really couldn’t think of a compelling reason not to, and there were all kinds of urges in her aching to find out how it felt. It would have been so much easier if he just had been the barbarian and thrown her on the bed and taken her. But as much as she hated it, she was in control of the situation. He wouldn’t take her unless she gave herself to him.

It was as scary as it was exciting, but she decided to go ahead and invite him to join her upstairs, into her bed, into her body. But first she’d have to get ready. Remembering Kay’s advice, she went into her bathroom and found the box of disposable enemas. After reading the instructions a couple of times through, she wriggled out of her panties and lay on her bathroom floor in just her waist nipper and stockings. She uncapped the little bottle, stuck its lubricated tip inside her, squeezed as much of the fluid into her passage as possible, and took the bottle out. There were some weird bubbly noises and a vague feeling like indigestion, and then she urgently had to sit and let it pour out of her. It left her feeling pretty empty, but just for good measure she did the whole thing again, and when it came out the second time, it was mostly just water.

Now she had to pick out the right outfit for seduction. She walked over to her closet and looked through her lingerie, regretting that she hadn’t figured this part out before her date. She wasn’t even sure if there were any negligees in her wardrobe; she’d never had a reason to wear one before. But eventually she found some very sexy things in a drawer. She wanted something that would show off her best assets, without calling attention to her liabilities.

There were some things she liked, but they seemed kind of complicated. Whatever she ended up wearing, she didn’t want Joe to have to take too much time figuring out how to take it off of her. A few were too long, and some were too short, but then she found it. It was a black silk nightgown. At the top, it was fitted like a bra, and even had a little bit of push-up action going on. There was a ribbon that tied between her boobs in a bow, and below that it was split in a flyaway style all the way down to her ankles. Joe would merely have to pull that ribbon and her gown would come open to expose all her fun parts!

Perhaps some parts were just a little too exposed. She looked around and got a cute little black silk g-string that matched the gown. It had a tiny little strip of elastic in the back, and Dee imagined that if Joe didn’t want to take it off her he could just push it over to the side and have plenty of access.

That started her thinking about preparing her area like Kay had told her to. She found the bottle of lubricant in her nightstand drawer, and tried to figure out how she was going to get some up inside her so that she’d be slippery and ready for a visitor. She took her negligee off so she wouldn’t get it messy, and slipped off the g-string. While she was down there, she took the time to refresh her tape, making extra sure that everything was tucked up and hidden away. She didn’t want anything breaking the illusion that she was a complete and natural woman.

She lay face down on her bed and tried to aim the bottle at her little rosebud and squirt the liquid inside. That didn’t quite work. She’d have to hold herself open to get the lubricant in, and that was too difficult. She opted instead to spread the lubricant on her finger, and then stuck it down in as far as she could get it to go. It was a strange feeling, and she had to be careful with her long fingernails, but she ended up getting a fair amount inside. Then she went to her bathroom and washed her hands, and then used a damp washcloth to clean off some spillage on the outside of her buttocks. She then pulled her g-string back on and looked in the mirror, enjoying how it covered just enough to hide her secret.

She pulled her gown back on and tied the little bow in the front, then adjusted the position of her boobs in the cups, making sure it was creating a sexy cleavage. She checked the mirror and everything looked pretty good, but she really didn’t think the waist nipper worked with the whole look. She unhooked it and took it off and there were some stripe-like marks on her tummy. It wasn’t quite as desirable, and her waist suddenly had no definition.

As if that weren’t bad enough, the mirror also showed that somewhere in there she’d gotten a run in her left stocking, either when she was running around getting ready or perhaps earlier when Joe was massaging her legs. She took her stockings off and there were also more marks on her body, ring-shaped dents around her thighs where the silicone strips that held her stockings up had been.

She was almost ready to give up when she had a brainstorm and hit upon the perfect solution to both her problem areas. She dug around her lingerie drawers and found a black garter belt that matched her gown well enough. She fastened it on and it helped define her waist, and when she rolled a pair of sheer black stockings onto her legs and clipped them into the six garters, the marks on her thighs were covered.

A pair of black satin mules with marabou trim seemed like the right shoes for her seduction scene, a sexy slipper to show she was ready for bed, and ready to be bedded. To add to the casual look, she let her hair down and added a few more curls with her iron. She stripped her jewelry down to just her earrings, but then decided she needed to swap them for a pair of beaded hoops that she could sleep in, to continue the idea that she always looked this glamorous at bedtime.

A couple more spritzes of perfume for good luck, a fresh coat of gloss on her lips, and she was ready. Dee slowly opened the door then stepped out, striking a pose. She was turned partially to the side, so her breast would be seen in profile, and her left leg was showing in the slit in her gown. She cooed, “Joe, could you come here please?”

She held her position and waited, but couldn’t hear his footsteps on the stairs. Perhaps she wasn’t close enough for him to hear. She slithered in her most sultry sashay down the stairs, and got into position at the landing. “I’ve got something for you, Joe,” she said in her smokiest voice, letting her lips stay pursed in the O position at the end of his name.

He still wasn’t showing up. She took a moment to rein in her temper, and then delicately stepped around the corner to the living room. She paused in the doorway so he could get a good look at her, but she saw that her audience was gone. She peeked into the powder room to see if he’d disappeared in there, but no luck.

Her third time through the living room she finally noticed a small blue piece of paper on the coffee table. It was about 5” by 8” and folded in half. “Dee” was written on the outside in neat cursive handwriting. She sat down on the couch and unfolded it. There was a note on the inside. Joe must have brought stationery with him. She wondered if it was in his jacket pocket, or if he’d fetched it from his car. She read the note.

“Dee,
At first I thought you’d just gone up to use the can, but when you didn’t come out after an hour I realized what had happened. Kay told me this was your first date with a guy, so I understand that you got scared and hid from me when things started moving a little too fast for you. I’ve seen it happen before. Try not to beat yourself up about it. When you’re ready, you’ll know it. You were a first-rate cocksucker, and if it was really your first time, you’re a real natural! I’m sure you’ll probably be just as incredible in the sack, and the guy who gets to take you there will be one lucky son of a bitch!

I did have a great time with you tonight, and I would love to see you again — it wouldn’t even have to be professionally. I can’t think of anything I’d rather do than take you out on a real date. You are smoking hot, better looking than like ninety percent of the real women out there, so don’t let anybody try to put you down just because you’re a tranny. If you’re interested, give me a call. Kay’s got my number.

Thanks again for an amazing night,
Joe

P.S. I put your dessert doggie bag in the fridge for you.”

There was a part of Dee that was relieved that she didn’t have to go through with it, but most of her was feeling frustrated and more than a little pissed off at herself. Had she really taken that long to get ready? Why hadn’t she just shouted downstairs to let Joe know she was willing, but needed to prepare?

She was also kind of mad at Joe. He couldn’t have come up and knocked on her door if he thought she was feeling too scared to come out? And what was with his crude vocabulary? And what kind of idiot was he for not putting his phone number in the stupid note?

If only she had his number, she could have called him and said, “Joe, it’s Dee. Get on back here. If you’d only been a little more patient, you’d be screwing my brains out right now.”

Dee did have the number for Jack, the cute guy she’d met in her dance class. She could give him a good old-fashioned booty call. “Jack? It’s Dee. Are you doing anything? I’m home alone and aching to have a man inside me.” Although she probably ought to warn him, “By the way, it’s going to have to be from behind, since I don’t actually have a vagina… Well, because I have a penis instead, but that’s not a dealbreaker is it? Really, I don’t think that kind of language was necessary!” It probably wouldn’t go well.

Dee went back up to her room and tried to get up the courage to use even her thin vibrator on herself, but couldn’t do it. She didn’t want to have to be both the man and the woman. She wanted to lie there and lose herself in the desires of another, to feel herself being penetrated, and not to have to also be the one doing the penetrating. She gave up.

In an effort to make her unsatisfied urges go away, she went down to the kitchen and nibbled on her leftover cheesecake and drank two cups of Kay’s special anti-aphrodisiac tea, brewed extra strong. She didn’t want to be thinking about sex again for a long time, not until she saw her girlfriend again, which really wasn’t that far away, only three more days.

Back upstairs, she cleansed the makeup from her face, moisturized, and then changed into her frumpiest nightgown and went to bed, hoping that maybe in the morning this whole disaster would feel like just a bad dream.