Christy's Fantasy Come True Ch. 01

Story Info
Chris realizes one of his crossdressing fantasies.
3.3k words
4.53
132.5k
36

Part 1 of the 10 part series

Updated 10/22/2022
Created 04/24/2005
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Chris walked through the door of his house Friday afternoon glad the week was over. He dropped his briefcase and coat at the door and headed straight upstairs. It had been a long week and he was looking forward to his usual Friday night ritual to relax. Heading to the bedroom he stripped off his clothes, went into the bathroom and turned on the water. As the tub filled with hot water he reached into the medicine cabinet and got out the depilatory cream. Once the tub had filled he slipped into the hot water and felt the tension from the week just melt away. After a few minutes of relaxing he grabbed the cream and began to rub it into his legs chest and arms to get rid of the stubble that had formed there over the last couple of days. He then set to work shaving his face and groin so he was nice and smooth all over. Satisfied that he was nice and smooth all over, he got out of the tub and toweled off.

Slipping on a bathrobe he moved back to the bedroom and began rummaging through his closet. Feeling in a bit of a sexy mood tonight he picked out a black mini-skirt, royal blue blouse and his 3" black heels. Laying those out on the bed, he walked over to the dresser and fished out his favorite black lace garter, thigh high hose, silk bikini cut panties, and lace bra. As he began slipping on the hose his and garter his cock began to harden as it always did when he first slipped into his feminine clothes. Slipping on the panties made it even harder. After putting the bra on he slipped his pair of false breasts in place and gave them a squeeze, they felt so lifelike. Once his lingerie was in place he sat down at his mirrored dresser and began to apply his makeup. First a little bit of concealer and blush, then some violet eye shadow and eyeliner. Moving onto his lips he picked out a deep shade of glossy red lipstick and applied that. Satisfied that was done he picked up his wig and clipped it in place on his head. He stood up and admired himself in the mirror. 'God I'm sexy' he thought. The curly, red, shoulder length wig framed his face nicely.

Walking over to the bed he slipped the skirt up over his long toned legs and zipped it up. Next he put on the blouse, buttoned it up, and tucked it in place. Last but not least he sat on the bed and slipped on his 3" strap heels. They always made his legs look sexy. Standing up he admired himself in the mirror again twirling around and prancing back a forth a bit. "Not bad if I do say so myself."

Chris was now ready for a night relaxing at home all dressed up as his alter ego, Christy. He had never gotten up the courage to go out dressed so he just stayed at home sipping wine, watching some porn, and luxuriating in his feminine clothes, always thinking about what he would do if he ever went out dressed up and managed to find some hunk to bring home.

Chris had never had another cock before but had fantasized about it a lot. It started out 10 years ago when he would wear his then girlfriend's panties and then some lingerie. After they broke up he took it a step further and began buying hose, garters, shoes, and then the clothes to go over them. The final step came a couple of years ago was when he got a wig and some makeup to make his transformation complete. Chris spent some nights dressed in lingerie and chatted online with people about how he fantasized about sucking a cock and being fucked in the ass by another man while dressed up, but on the weekends he went all out and put on his lingerie, clothes and makeup. He would get out his dildoes, butt plugs and nipple clamps and play with them. Stuffing a butt plug in his ass he would then go down on the dildo, sucking it like a real cock. After a while doing this he would then slip the dildo in his ass in place of the plug and ride it until he came all over his hands. Then he would lick it up, reveling in the taste of his cum. On some occasions he would bend over backwards so he could shoot straight into his mouth and all over his face. He would fantasize about being taken by a man or two men at once when he did this, always cumming in vast amounts. Most men he though of were just visions in his mind except one, a friend of his whom he fantasized about a lot, Jim.

Chris' friend was about his height, 6'3", toned body, deep blue eyes and short blonde hair. Chris never would have suspected him of being bisexual or gay until one night when he was out with Jim and his girlfriend. Over dinner his girlfriend mentioned that she was bisexual and then made an offhand remark about Jim trying something they discussed once. She did not elaborate but Chris had a good idea of what it was. That was a year ago and Jim had since then broken up with his girlfriend. Chris and Jim got together about once a week but he had never gotten up the courage to broach the subject of sex with men with Jim.

Chris had been dressed for a couple of hours now and was lounging on the couch sipping some wine, gently playing with his nipples, his cock straining in his panties. He was getting ready to pop a video in the DVD player when he heard the doorbell ring. Startled he looked up. He wasn't expecting anyone over tonight. The bulge in his panties began to shrink. He thought if he didn't answer the door maybe they would go away. No such luck. After a couple of minutes the doorbell rang again. Taking a few deep breaths he walked to the door and looked through the peephole.

Standing on the porch was Jim. His mind was racing. Here he was all dressed up and Jim on the front porch. Chris' mind was racing, thinking to himself that this might be the night to see if Jim was bisexual. He could let him in pretend he was housesitting and then seduce Jim. Smoothing out his dress he opened the door a crack. Peering around the corner, he said, "Hello?" in his best feminine voice.

Jim looked a little startled. "Um, hello. Who are you?"

"I'm Christy. Who are you?"

"Jim, a friend of Chris'. I didn't realize he had company over."

"Oh," Chris relieved that Jim didn't recognize him. "I'm house-sitting while Chris is out of town for a week. He said I could stay here. Would you like to come in?" He opened the door wide and invited Jim in.

Jim took the invitation and walked in. "Thanks. I was just stopping by to see if Chris wanted to go out for a couple of drinks and unwind after a week at work."

"He decided to take off yesterday for a long vacation. He called me to see if I could house-sit for him on short notice so I said yes as long as I could use the house." Chris replied. "Would you like a drink?"

"Sure."

Chris walked into the kitchen. He could feel Jim's eyes taking in his long legs and ass as he disappeared around the corner. He loved the attention. After pouring some drinks he walked back into the living room. Jim had made himself at home on the couch. Chris sat down beside him and handed him the drink.

"Thanks. This will really hit the spot after the week I've had. So how long have you known Chris?"

"Oh, about 20 years. We've been friends since grade school and have kept in touch." Chris smiled inwardly at himself.

He could see that Jim was looking him up and down now. Chris could barely contain himself. He wanted to jump on him right there and eat him alive but he had to move slowly here. He began by gently running his hand across Jim's leg closest to him. Jim smiled at him.

"So you're here all week with nothing to do?" Jim asked with a gleam in his eyes.

"Yes," Chris replied "all week with nothing to do. I live about an hour away and don't know anyone here." He was lying through his teeth but hoped that Jim would buy it. Jim's next moved confirmed that.

He put his hand on Chris' thigh and leaned in towards him. "I can't help but think you are a hot woman Christy."

Chris looked back at him and replied, "Thanks Jim." Hoping not to scare him away. "You look pretty good too. So what did you have in mind?" Chris looked into his eyes and smiled, hoping that he could seduce Jim the rest of the way.

Without saying a word Jim leaned in and began kissing Chris on the lips. Moaning Chris responded in kind, slipping his tongue into Jim's mouth in return. This was working out better than he expected. "Oh my, I like what you have in mind Jim." Chris moaned.

They sat there on the couch for what seemed like an eternity. Chris's hands were running up and down Jim's back as they made out kissing each other, tongues slipping in and out of their mouths. Chris would kiss his way from Jim's mouth to his ear and nibble on it. He liked that and thought Jim might too. He was right. When he did that, Jim moaned and hissed through clenched teeth, "Mmmm". Jim was now grinding his hips into Chris' leg. Chris could feel Jim getting hard and so was he. He hoped that Jim didn't look down and notice the bulge in his dress yet. Chris moved his hands lower to his crotch and repositioned his cock so it would not show.

Jim saw him do that out of the corner of his eyes and began to move his hands to take the place of Chris', wanting some of what was in there, or so he thought. Chris brushed his hand away. "Uh-uh. Not yet Jim," Chris scolding told him. "You can't have that yet." Jim looked disappointed. "You'll get what's coming to you soon enough" he said with a grin on his face.

Chris stood up and sauntered over to the stereo and turned it on. A slow sexy beat began to play in the background. His hips began to sway back and forth. He was imagining in what he was going to do to Jim and what Jim would do to him as he began to grind his hips to the music, running his hands up and down his body. A low moan escaped his lips. As he did that Jim began to moan also. Chris looked over his shoulder and noticed Jim watching his tight ass and rubbing his crotch.

"You like what you see Jim?" Chris asked knowing the answer, but he wanted to hear it.

"Mmm, yes" moaned Jim.

"I thought so." he replied as he walked over to Jim slowly. As he did he moved his hips to the beat of the music, slowly unbuttoning his blouse as he went. Jim was watching Chris move towards him his eyes locked on Chris'. He smiled as Chris came closer and put his hand oh his crotch, feeling his hard cock through the pants.

"Mmm, why don't you slip out of those?" Chris cooed." I'm sure you'd be more comfortable."

Jim heartily agreed as he slipped of his pants and boxers. Chris was helping unbutton his shirt. As he did so he rubbed his hands over Jim's nipples, pinching them lightly and then leaning in to lick them one at a time. Jim drew in his breath at this sensation and gasped. Chris moaned liking the reaction he was getting out of Jim. He could feel his hands begin to rub his hose covered legs and begin to climb higher on his thigh. Not wanting Jim to find out just yet he backed off.

"Ah ah, not yet" Chris scolded him, wagging a finger. He dropped to his knees and began doing a dry hump on the floor. Watching Jim begin to play with his cock was turning Chris on. He began to rub himself all over pinching his nipples and rubbing his hardening cock. Pausing fir a moment, Chris finished stripping off the blouse to show Jim his lacy bra and fake 36C tits. Squeezing them as he arches his back, thrusting his chest towards Jim. As he does this he realizes that his cock is rock hard and probably showing an outline in his skirt. He quickly straightens up and looks at Jim.

Jim was still stroking his cock, his eyes glued to Chris' body. As far as he knows Jim did not see anything. Chris drops to all fours and crawls between Jim's legs and begins to lick his cock. Slowly at first, reveling in the taste of his first cock. He had dreamed about this moment for so long he couldn't believe it was happening. Jim ran his hands through Chris' hair as Chris began licking his cock like a lollipop, Jim moaning his approval. Chris moved to the head of Jim's cock taking it in his mouth and began to slowly swallow Jim inch by inch. He was even bigger than Chris had imagined. It took some doing but Chris managed to get Jim's cock down his throat. He began bobbing up and down on Jim as Jim slowly fucked his face.

As this went on Chris began to shimmy out of his skirt. Now down to his lingerie, he could stroke his cock as he sucked Jim. Moaning with pleasure he began to rub and stroke his cock faster taking Jim deeper and deeper. He could hear Jim's moans mingle with his own, turning him on even more. Chris was now kneeling slightly to the side as he stroked himself, not paying to much attention to weather Jim could see his cock or not at this point. Jim's hands began moving over Chris' shoulders to his tits massaging them. At this moment Jim opened his eyes. He wanted to get a look at Chris in his lingerie. He looked down and thought he saw a cock poking through the panties around Chris' waist. Doing a double take he looked again. Yes it was a cock he saw. He stopped massaging Chris' tits and just stared. As Chris sucked Jim he noticed that he stopped massaging his chest and was no longer moaning.

"What is going on here?" Jim said, a little shocked. Chris looked up at him, with his cock still in his mouth realizing that Jim could see his cock.

"Well", Chris began to confess," I'm a man. In fact, it's me, Chris." Jim looked at Chris' face for a minute and then he recognized him.

"Oh my god, it is. But the wig, the makeup, why the disguise?"

"I have been dressing like this for a couple of years now. Most recently fantasizing about you. I dress up like this every weekend at home. I wasn't expecting you, so when you showed up I thought I could seduce you since you didn't recognize me right away." He paused to lick Jim's still hard cock. "It looks like I succeeded."

"Oh you did alright. I never knew this about you. But how did you know I would like it and not freak out?"

"I had my suspicions." Chris smiled as he licked Jim's cock again. Jim moaned with pleasure. "Shall we continue?"

"Please do." Chris began to lick and suck Jim's cock again. He could swear it was even harder now. "Let me suck you too Chris."

"Not tonight." Chris replied. "I want to fulfill my fantasy here first." Chris began deep throating Jim, taking his cock all the way into his mouth. Jim's moans of pleasure were music to Chris's ears. He began to stroke himself faster and faster as he sucked Jim close to orgasm. Jim was thrusting slowly in and out of Chris' mouth, in time with Chris's head motions, adding to his own pleasure.

As Chris continued to deliver the first real blow job of his life Jim began to pull him off of his cock. Jim pulled Chris to him and began kibbling on his ear. He whispered," How would you like my cock in your ass?"

Chris pulled away from Jim, looking him in the eyes and beaming. "I thought you'd never ask. I have fantasized about riding your cock so many nights while I play with myself." Chris straddled Jim's waist and began rubbing Jim's cock up and down his crack. Pausing for an instant at his tight little hole, reveling in the fact that his ass was about to be fucked by a real cock. Slowly he sat down on Jim's hips. The head popped in and Chris just held it there.

"Mmmm, you are nice and tight Chris." Jim moaned. "You feel so good."

Chris began to slowly impale himself on Jim's cock taking it inch by inch until he had all of that big cock in his ass. "Ohhh, you are so big, filling my tight ass, it feels so good to have a real cock in me." He just sat there for a minute as Jim began to squeeze Chris' breasts.

"Let's get rid of these so I can play with your nipples." Jim said. With that, he reached in and pulled out the fake breast forms, giving him access to Chris' hard nipples. While Chris was getting used to the cock in his ass, Jim leaned forward and began to lick and bite Chris' nipples. Chris moaned as he did this and began moving back and forth on Jim's hips. Jim's cock was stretching his ass wide but it felt so good. After a few minutes of grinding on Jim's cock Chris was moving up and down on it, letting it slide in and out of his ass. Jim was keep rhythm with Chris as he pistoned in and out of his ass, moving in the opposite direction as Chris so he could get the full effect of his cock sliding in and out of Chris's rear passage.

Chris was close to cumming by now. He was stroking his cock faster and faster and moaning with pleasure. He began moving up and down on Jim's cock faster also. "I'm close to cumming baby. Cum with me, fill my ass with your sticky cum." Jim was more than happy to oblige. He thrust into Chris' ass a few more times before he groaned and moaned "Here it come Chris."

With that he let loose a torrent of cum, filling Chris's ass with spurt after spurt of hot sticky fluid. It was enough to drive Chris over the edge. He stroked his cock one last time before it erupted, sending thick streams of cum up into the air between him and Jim. The cum landed on Jim's chest with every spurt. Spent, Chris relaxed on Jim's lap and leaned in to lick his cum off of Jim's chest. He then moved up to kiss Jim and feed it to him. Both of them kissed and held each other for a few minutes, basking in the afterglow of incredible sex.

"Pretty kinky aren't you for your first time Chris?" Jim asked.

"I've been thinking about this for a long time and never knew how to bring it up. I'm glad you stopped by. Hopefully this won't be a one time thing." Chris mentioned as he looked at Jim.

"Oh no, it won't be. That was the most incredible sex I've ever had. And it definitely won't be the last. Maybe next time I'll take you out and show you off."

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AnonymousAnonymousabout 1 year ago

Many hot, erotic things in this story but one of the best parts was Christy taking off those stupid fake breasts so Jim could get at her nipples! God, how I love playing with and having my nipples played with! Adds SOOOO much to erotic gay CD sex, I love twisting them hard as I cum!

AnonymousAnonymousabout 4 years ago
Finally Fullfilled !!!

Your hot thread gets right to the point...no pussy-footing around. Christy finally gets hur man...Jim...Mmmmm!!! Christine has similar fantasies, and luvs💓 the pace, and descriptive writing style. I'll be hand-washing numerous panties, reading more of ur delicious thread....not complaining in the least!!!

SissyCrissy6245..........xoxoxo

AnonymousAnonymousalmost 10 years ago
I'm a closet CD too

Like some other readers of this story, I too am a closet CD. I just recently started going out in public with my new lover -- who is my best male friend. Just like in your story, he came over to my apartment unexpectedly and caught me dressed up. It was a bit different than your story because he knew right away it was me (I'm not fully passable yet). However, he told me he'd always fantasized about being with a CD and I told him I'd always fantasized about being with him. When he leaned in and kissed me -- oh my God that was heaven. As you know, kissing a man while dressed as a woman is one of the most incredible experience ever. Later he made my dreams come true as he fed me his big juicy cock to suck and he then fucked me -- actually he "made love" to me (I'm in love with him & I'll always be his lover). He makes me feel so wonderful that I want to "come out of the closet" for him. I'm truly a sissy faggot cocksucker who wants the whole world to know. Your story has helped both of us realize the truth. Thank you.

AnonymousAnonymousover 12 years ago
Great Story

I am a closet CD as well, and have fantasized many time riding a real dick instead of my wife's dildo. Maybe I will have the courage to do so soon! thanks for the great story!

pantymichellepantymichelleover 12 years ago
Very sexy!!

Loved your story. Soooo very sexy. I'm a closet CD as well and I wish something like this would happen to me. Can't wait to read more. I'd love to chat with you as well.

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