Bob Dresses for HalloweenbyLaffWithMe©
The following material is protected under the copyright laws of the United States of America. This work may not be distributed for profit, in any form, without the written permission of the author or his agent.
* * * * *
Bob was trembling as he walked through the women's section of the large department store. There were very few people in the store this morning, yet he was certain that each of them was watching him. Seeing his wife should have calmed him but it didn't.
"See, Bob, I told you the floor would be empty this morning. Come back to the fitting rooms, I think I've got some great outfits for you to look at."
"Jesus Casey, I don't know if this is really going to work. Maybe we should forget it." Bob replied.
"Oh no, you're not going to chicken out on me now." Casey grabbed his arm and pulled him through the curtain, then into a small cubicle. "You said you wanted to do it and I think it's a turn-on. Anyway, you'll never know if you like it until you actually try it. And what better time than Halloween?"
The 'it' in question was something that had haunted Bob since he was a teenager, maybe even before that. The 'it' was his fascination with women's clothing - no, not a fascination, a desire to dress in women's clothing. It was more than just dressing the part; he knew down deep, that he wanted to experience being a woman.
"Now strip while I go get your new wardrobe". At this point it seemed that Casey was more excited about this adventure than Bob. As the cubicle door swung closed, Bob stripped to his nylon bikini shorts. He watched himself in the mirror as each piece of clothing was removed. Then, almost naked, he examined himself more closely, trying to imagine how he would look in... Shit, he had a hard time even thinking of the word... 'drag'.
Still, he did think he had a nice body, for a man or a woman. His five foot eight inch frame was lean and firm. He had continued to swim and run marathons, the sports that had gotten him small scholarships in college. His rich brown eyes made a nice contrast to his fair Nordic skin and collar length blond hair. His nose was very straight; it almost seemed to be a pointer to his lips that were slightly large and full in appearance. He shrugged his shoulders, flexed his muscles slightly, and noticed his nipples move as he did so. He absent-mindedly pinched one and brought it to erection. His nipples were almost as large as Casey's were and very sensitive. His bikini shorts were snug and he could clearly see the outline of his cock and balls. Turning to view his profile, he decided that he had a nice ass atop his well-shaped legs.
Casey was suddenly back with an armload of clothing. "Preening?" she said. "Here, start with these panty hose, but don't get attached to them. I think some nice patterned nylons will look better.
Bob opened the package and removed the pantyhose, pausing to feel the texture. Casey watched and smiled. As Bob slipped on the stockings he saw the look in Casey's eyes. That same look when she had caught him trying on her pantyhose a few weeks before. He had been embarrassed and ashamed when she walked in, fully expecting her to be furious. Instead she had a devilish look in her eye and a clearly mischievous grin on her face. Bob had known early in their relationship that Casey enjoyed some unusual sexual activities. In fact, when he met her, he thought she was gay. Thus it was no real surprise when she was the one to suggest that he dress for Halloween.
Casey knelt in front of Bob and smoothed the stockings from ankle to thigh. The feel of her hands sliding over the nylon on his legs, the press of the panty top against his cock caused his cock to swell. Casey looked at the sharp outline of the hard cock bulging against the thin shorts and sheer pantyhose. She could clearly see the balls separated by the seam of the stockings, the shaft pressed to the side, the flair of the cock head.
She pressed her face to the knob and kissed it lightly. "Well sweetheart, I see we're going to have a problem hiding this little monster" she laughed. Not that Bob had a monster. On the contrary it was probably slightly small, but in Casey's view was perfectly shaped. The shaft was very straight with a prominent blue vein down the side. Casey loved feeling this vein bulge and pulse as her tongue caressed it. The shaft was crowned with a large head that looked like some kind of helmet. What Casey enjoyed most was the fact that this cock would get extremely hard. When Bob got aroused his cock truly felt like a bone wrapped in warm skin.
"Casey, I don't think we should do anything here. Let me just try on the clothes before anyone comes in." Bob knew that his wife loved sex just about every way except in the bedroom with the lights off. Despite his hard cock he didn't want to be fucking in the women's fitting room of the biggest store in town.
Casey rubbed her cheek against the solid bulge. "But sweetheart, you can't try on clothes with this big cock sticking out. It'll ruin the line." She was hooking her fingers into his briefs, pulling down the panty hose and briefs together. In a second his cock sprung free of the confinement.
Casey talked to the cock swaying in front of her nose. "Oh poor baby, you're so pale and white. Hasn't daddy let you play out in the sun? Let mommy kiss that pretty pink head of yours."
She grabbed the shaft, brought it to her lips and began kissing the end. She held the tip to her lips and french kissed it several times, licking the point of her tongue into the hole. She soon was rewarded with drops of precum oozing out to meet her tongue. She tightened her grip on the bone; watched the head turn a darker shade as she squeezed the blood engorged shaft. The blue vein swelled and she licked it then sucked the cock into her mouth.
Bob groaned and gave up to the pleasure. He held her head and began pumping his cock into her mouth as she expertly sucked and tongued the shaft. Her hand worked the shaft back and forth, jacking him off into her mouth. She reached down, pushed her hand beneath her waistband and began finger fucking herself in time to the cock fucking her mouth. Bob could hear voices in the distance but it was too late to stop. He felt his juices begin to boil. He moaned and fucked her face harder. Casey let her tongue work its magic and quickly brought Bob to a climax. She felt his cock pulse in her hand; she sucked and drank as the cum spurt into her mouth. She rubbed her own clit rapidly, achieving a small orgasm for herself.
"Now, don't you feel better?" she said as she stuffed his now limp cock back into his briefs, then pulled them up along with the pantyhose.
Casey stood, retrieved a lacy black bra, which she slipped onto him. Bob shivered with excitement as she snapped the bra in place. The bra had padding in the cups and he could feel the structure of the bra pushing against his pectorals. "I was thinking of going for bigger boobs," he said, as he looked down at the small cups.
"Oh shit, you guys and your tit mania! Look, big tits will look really fake on you. Look in the mirror, this thing actually gives you a little bit of cleavage."
Bob turned to the mirror and leaned forward slightly, amazed at how sexy he felt in bra and panty hose. Marveling that indeed this bra managed to push his chest enough to give a hint of rounded flesh.
"Here you go, baby, you're going to like this." Casey pulled a black sheath from behind some other dresses. "Slip this on."
Bob wiggled into the dress, feeling it cling to his body. He felt as if he was wrapped in black SaranWrap. The dress fit perfectly. It had a long slit up one side; no sleeves, a high neck and a heart shaped opening in the bodice. The point of the heart accentuated the newly formed little tits that the bra forced up.
"Here. Step into these shoes." Casey slid a pair of low heeled, black, open shoes onto his feet. "Move around a little bit now. Let's see how this is going to work."
Bob stepped haltingly back and forth in front of the mirror. Wobbling on the low heels, he looked rather ungainly yet he was clearly going to be striking in this outfit. He moved his leg and watched as the slit on the dress opened to reveal skin almost to his ass. "Goddam baby. You do have a pair of legs! Let's see how that ass looks." Casey turned him to view a profile. His ass bulged out seductively; his chest had a nice curve as if he really had firm small breasts. His cock was again throbbing and pushed out at the material! "Oh shit, sweetheart. We just have to do something about that cock of yours. We'll have to try some tummy tuck panties, maybe the elastic will be enough to contain you."
All in all, even without makeup, Bob had become a very sexy looking girl. He could hardly contain his excitement.
"Let's try on a couple of these other dresses, but I think that one is going to be the best", Casey said.
Reluctantly, he removed the dress and tried on the others that she had brought him. However, nothing could top the sheath with the slit up the side.
In the days that followed, Bob practiced walking in his new heels. He insisted on wearing his new outfit every night, to the point that Casey had to stop him lest he wear it out before the big night.
She taught him how to sit, how to walk. She tried to teach him how to dance. This turned out to be the second most difficult part of the transition. They made some progress but decided not to worry about it. They would be together and would only be dancing with each other so they figured no one would notice who was leading whom.
Even more difficult was Bob's voice. Unfortunately, although his body was not large, his voice was very deep. They decided that Casey would do all the talking whenever possible. Bob would limit himself to one word answers or better, just utter 'uh huh', 'ummm', etc.
Finally, Saturday arrived. Bob was so nervous he couldn't shave himself. Casey carefully shaved his face, then his legs and arms and underarms. She helped him dress, and then draped a towel around him as she applied the final touches of makeup. When she was finished, they both agreed that he was now a very attractive she.
Casey would be the husband tonight. She dressed quickly and didn't worry too much about it. Although she had been to a few lesbian affairs where she dressed as the man, she didn't get excited about it. Even so, her athletic body allowed her to be a very passable male. As they were about to leave, they paused for one final look in the mirror. They looked like any couple dressed to go to dinner or dancing except that Casey wore a black eye mask and Bob wore a rhinestone crown on his head. Beyond that, the only thing that looked unusual about them was the fact that 'Bobbie' was a few inches taller than Casey.
When they pulled up to the valet parking at the hotel, Bob started to open the door. Casey caught his arm. "Wait, honey, let the boy open it."
Just then a grinning teenage boy opened the car door. As Bob swung his legs around to get out, the slit in the dress opened to reveal his complete leg. He heard the sudden gasp of the boy as the teenager helped him exit the car. Bob's heart jumped. He looked at the boy's face and saw the horny young eyes staring at the body in the black dress.
Casey came around. "C'mon sweetheart. Let's not get the boy's hopes up", she laughed. Bob was thrilled, that kid was actually looking at him and seeing a woman.
They made their way into the ballroom, which was nearly filled. The range of costumes was phenomenal, some obviously rented for the occasion; others looked as if the wearer had prepared for months for this evening. All of the tables anywhere near the dance floor were occupied. Casey spotted some empty tables in a distant corner and directed Bob to one of them. They were both getting into the role reversals and Bob allowed Casey to pull a chair out for him.
As they walked across the floor, Bob pulled his shoulders back and pushed his small boobs forward. He was rewarded with a few glances from men in the area.
Casey ordered whiskey sours for both of them. She flirted with the waitress who didn't seem very interested, or maybe realized Casey was female in drag. Bob drank his drink rather quickly and Casey ordered another. "Slow down sweetheart. We're going to be here for a few hours. I don't want you to get sloppy drunk and run off with some guy," she laughed. They chatted, watched the crowd and finished the second drink.
"Ok, before you start your third drink, I think we should dance", she said.
"Not yet. I don't think I can do it here in public."
"C'mon. I'll lead, you just follow. Nobody's going to see you if you just sit here in the corner" she coaxed.
That was the magic word. Yes he wanted to be seen. He wanted to flaunt his new persona, see heads turn to look at him. The music was loud and fast. Bob started cautiously but was soon dancing as seductively as he knew how. The dance floor was crowded and perhaps not as many men were looking at him as he imagined. Still he was certain that many of the errant bumps against his ass were not errant at all. He felt an occasional hand grab his well-shaped ass.
The band worked its way through several fast tunes with an occasional slow piece inserted to give them a rest. The band took a break; Bob looked at his watch. "Geez, almost 11. This is hot, I know some guy grabbed my ass", he said as they dropped into their chairs. Casey ordered another round of drinks.
The band returned, the music started. Just as Casey was about to take Bob out on the floor again, a man approached the table. "Excuse me, would you mind if I danced with your wife?"
"No, go right..." Bob began, only to be quickly silenced by Casey as she said, "I think she'd love another partner."
Bob froze. The man extended a hand, "Thank you, you do look fabulous tonight."
Bob hesitated. "Go ahead Bobbie, I'll just sit and watch," Casey said as she nudged Bob under the table. "She's a little shy, self conscious about dancing with strangers," laughed Casey.
Bob looked at the man dressed in a Spiderman costume. He appeared to be about 40 or 50, maybe six feet tall and slightly heavy. Probably once was athletic but obviously did not exercise. Bob allowed his hand to be grasped by the stranger. Casey and Bob both noticed the man looking at Bob's leg exposed by the slit in the dress.
"My names Ted. And you're Bobbie?"
"Is that short for Barbara?"
At last they were on the dance floor. At least it was a fast dance so Bob didn't have to worry about following. Also, the loud music and distance between them negated Ted's attempts at conversation. As the song progressed, Bob again began enjoying shaking his body. He found it very arousing knowing this man was watching every move he made. He felt the man's hand glide across his body whenever they were close.
The music stopped, Bob turned towards Casey at the table.
"How about one more? My wife's gone off with a friend and I really feel like dancing", Ted said as he grabbed Bob's hand. Bob saw Casey staring across the floor at him; she was grinning wildly.
"Well, Bobbie? Just one more? It doesn't look like your husband will care."
The music started. Bob turned and smiled at Ted, "OK". Another fast dance and Bob was now at his sexiest to date. He saw Ted's eyes savor the views of his leg as he thrust it out through the slit in the dress. He noticed that Ted frequently looked at the heart shaped opening, trying to see past the material to what Bob wished were real tits.
The music ended, Ted grabbed Bob in a final spin, holding him close for a few seconds. Then Ted took Bob's hand and walked him back to Casey. "That's one hot number. I want to thank you for making my evening. In fact, would you let me buy you two a drink?"
"Sounds like a good idea" Casey replied as she pulled a chair around for Ted. She placed the chair so that Bob was between them.
"You folks staying at the hotel?" asked Ted.
"No, we live here in town." replied Casey.
"Oh, we do to. This is our third year coming to this and we decided that it would be fun to get a room. That way we don't face driving home plastered." Ted laughed. "My wife met a friend and deserted me just when I was getting warmed up for some dancing. That's why I asked you," he said looking at Bob, "that and the fact that I saw you on the floor."
"Oh," Bob smiled.
As the music played, Ted bought a couple of rounds of drinks. He carried most of the conversation. Bob managed a few "uh huh's". Finally Ted asked Bob to dance, again a nice fast dance. Bob, feeling the glow of his whiskey sours, didn't hesitate this time. Casey didn't have to coax him; he was up quickly holding Ted's hand. When the dance ended, Ted held Bob's hand. "Another?" "OK," Bob whispered. The music started. It was a slow dance. Bob felt Ted wrap his arm around him. Without thinking about it, Bob was dancing. As the dance progressed, Ted pulled Bob against him. Bob became aware that Ted had a rather substantial hard on. He could feel Ted pressing his cock into him. He felt Ted's hand begin to rub his ass, soft firm squeezes, pulling Bob into the hard meat.
Bob's cock responded, it grew stiff and hard, pressing against the tummy tuck panties, pushing out against the panty hose, making a bulge in the black sheath dress. He was sure that Ted could feel his hard cock just as he felt Ted's.
"Umm, Bobbie. That feels real good. You are very good. How long have you been doing this?"
"Huh?" Bob worried.
"Dressing. How long have you been dressing?"
"Uh uh, uhno," Bob mumbled. His cock melted as he realized that this man knew.
Ted placed both hands on Bob's ass, pulled firmly and ground his cock into Bob. "You're the hottest I've seen. You can talk to me. Tell me, how long?"
"First time." Bob mumbled, unsure what to do.
"Un-fucking believable. This really is just your Halloween costume? I don't believe it, you're too good and too into it for this to be just for Halloween."
"Really, this is the first time. I, uh..uh.." Bob was nervous. He still felt Ted's hard cock pressing into him, still swayed to the music allowing Ted to grind the hard meat against him, was still enjoying the firm hands on his ass.
"Maybe, but you like it. I can feel it. You like showing off your legs, fantastic legs! You like having me look down your dress, checking out your tits. You feel my cock don't you? Feel it hard. I could feel you get hard to. I feel it getting hard again, right now," and Ted pressed his cock into Bob.
"Yeah, I do, I like it," Bob said, realizing that he was doing something he had always wanted to do.
The music stopped. The two returned to the table. Casey had been watching. She could tell that Ted had figured out Bobbie was Bob. What she wondered was how Bob was going to react.
"This thing's almost over. Would you two like to come up to my room for a nightcap? My wife won't be back for hours."
"What do you think Bobbie? Sounds like a good idea to me," Casey said.
"Ahh, I don't think so. If your wife comes back she might be upset." Bob fidgeted.
"Look, don't be shocked. She's gone off with a man we met here tonight. We have sort of an open relationship. She doesn't get turned on by some of my interests so we each have our own fun occasionally."
"What kind of interests? Casey laughed. "Not a serial killer I hope."
"No, no, no. Can I be honest? I'm bi. I get really turned on by TV's and TS's. I just thought it would be nice to talk for a while. I just can't believe this is Bobbie's first time out."
Bob flinched at this reference. He had never thought of himself as a transvestite or transsexual or even bisexual. This was going further and faster than Bob had anticipated. On the one hand he was reveling in Ted's attention and compliments, had gotten more excited than he ever imagined when he felt the man's hard cock pressing into him on the dance floor. On the other hand he was frightened at the prospect that this was probably leading to his first sexual contact with a man.