Christy's Fantasy Come True Ch. 04

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Chris decides to take his crossdressing a step further.
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Part 4 of the 10 part series

Updated 10/22/2022
Created 04/24/2005
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After everyone left the superbowl party Chris showered and cleaned up for Jim. He sat under the shower spray and soaped up his smooth body, paying special attention to his new breasts and his hardening cock.

As he cleaned up, he thought of the last few months with Jim; seducing him, going out on dates, getting fake breasts to be more of a woman and now tonight, being the center of attention in a gang bang. It turned him on getting fucked by all those men in front of Jim. And he knew that Jim liked it too, he told Chris as much after the party. Stepping out of the shower, he toweled off, slipped on a silk camisole and some panties and headed into the bedroom.

Jim was waiting for him in bed.

"You were incredible tonight Christy," Jim exclaimed. "And look, they left you with a sizable tip."

Jim handed Chris a wad of cash. He quickly counted it and it was over $1,000.

"Oh my, they must have really liked my performance. I certainly enjoyed giving it. Maybe I should start stripping for a living." Chris laughed.

Jim gave Chris a funny look. "You can't be serious."

"No I'm not honey, although it was incredible. You know I'll always love you but there are times where you aren't around that I get so horny. Especially when I am all dressed up and go out shopping or go out to eat by myself and guys hit on me."

"They do?" Jim asked.

"Yes, and sometimes I just want to take them home and fuck their brains out."

Jim looked at Christy with a mix of surprise and jealousy. He loved watching her with all those men tonight but wasn't sure if he was keen on her fooling around with other guys when he wasn't there and he told her so.

Chris crawled into the bed and snuggled up to Jim.

"I told you baby, I'll always love you. You liked watching me with your friends tonight and you loved it when I blew the waiter a few months ago in the back of your SUV while you watched."

Chris leaned in and kissed Jim on the cheek. "Besides, maybe one of these times I'll bring one home and we can both have some fun with him or if you're not around I'll tell you all about it later. And just to make things even, if you want to fool around on me with another man or woman I won't mind. As long as I get to hear about it too."

Jim smiled at the thought of that.

After sucking Chris off in front of all his friends at the party he was sure he wouldn't mind Chris brining another person home to join in the fun. Or, as Chris mentioned, being told all about his exploits later.

"Well, if you promise to tell me about your exploits later I guess it would be all right. But only when I am not around or we don't have anything planned."

"Oh, a little jealous are we?" Chris retorted. "Don't worry baby, no one can replace you. You're to good to me. I promise not to cancel dates with you."

Jim hugged and kissed Chris, feeling reassured that their relationship was still intact. Holding Chris tight to him, they fell asleep in each other's arms, tired from all the excitement from the party.

Waking up the next morning Chris slipped out of bed and took a quick shower. As he was in the shower, he began thinking of the money he had made last night. There must be a way to make a living while dressing as a woman. Then it hit him. He would start a service to teach men how to dress and behave like a woman. Stepping out of the shower he toweled off and went into the bedroom.

Jim had gotten up and was sitting on the edge of the bed.

"Morning sleepyhead."

Chris leaned in and kissed Jim on the lips. Going to the closet, Chris grabbed a change of clothes out of the closet. He had begun keeping a spare change of clothes at Jim's in case he stays over during the week or at the end of the weekend.

"I need to get into work early for a meeting but I'll be back here after work waiting for you. We can have some fun tonight. I have something I want to tell you tonight too."

"It will have to wait until I get back into town." Jim said groggily. "I have to go out of town for a few days."

Chris looked at Jim with a forlorn look on his face

"I was looking forward to having you all to myself tonight after last night.".

"Well, if you can't wait until I get back you can always go out and have some fun without me, as long as I get to hear about it when I get back." Jim replied.

"You mean it?" Chris asked with a hopeful look on his face.

Sitting up in bed Jim looked at Chris.

"Yes I do. Who knows? One of these times I might be able to watch again or join in the fun." "Oh honey, I love you." Chris beamed as he leaned in to kiss Jim. "I promise I'll tell you all about it when you get back."

He sat on the bed next to Jim and took his hands. Looking into his eyes, he decided to tell Jim of his plans now.

"I was doing some thinking in the shower about all the money I made last night. I want to dress like a woman more often and make money doing it.."

Jim got this worried look about him.

"Don't worry, I'm not going to strip or start prostituting myself. I want to start a business where I help men get in touch with their feminine side."

"Would it include having sex with them?" Jim asked.

"More than likely." Chris responded. "But I could use your help there as an assistant if you catch my drift."

Jim looked at Chris for a moment, trying to figure out if he was kidding or not. It finally hit him that Chris wasn't joking.

"It defiantly sounds intriguing. Would you let me fuck them?"

"If you like. I love you Jim and would do anything to please you. If you wanted to fuck them I would let you, especially since I would get to watch."

That thought turned Jim on, especially after watching Chris last night. He had a feeling that Chris liked watching too.

"Anything to keep you happy baby." Jim finally replied. "Sounds like it could be a lot of fun."

Chris threw his arms around Jim and hugged him close.

"Oh thank Jim. I was hoping you would be agreeable to this."

Standing up, he walked to the bedroom door, turned around and blew Jim a kiss.

Jim smiled back at him and did the same.

"See you when I get back." Chris cooed as he flashed Jim a mischievous grin.

Chris couldn't wait to get home from work and change into something sexier than his work clothes. All he could think about at work was getting home, changing, and going out on the town to find some fun. He had been searching the Internet, looking for ideas to start his business. He found some sites that advertised the kind of service he was thinking of starting. They sold lingerie, breast forms, slimming corsets, and all sorts of other supplies for cross dressers.

After returning home from work, Chris wasted no time stripping off his work clothes on the way to the bedroom. He rummaged in his closet for a sexy outfit to slip into before going out. As he was flipping through his dresses he came on the one-piece outfit Jim had given him for his night on–the-town with him, dressed as a woman. He thought that would be the perfect outfit to wear tonight.

Throwing the outfit on the bed he turned his attention to what lingerie he should wear. As he turned to rummage through his lingerie chest, his eye caught the video camera he put up there a few nights ago. He had planned on taping himself getting dressed in his lingerie, doing a sexy little dance for the camera, and then fucking himself with his toys. He was then going to give the tape to Jim as a present for when they couldn't be together.

Then an idea hit him. He was going to set up the camera to record his fun tonight and give that tape to Jim. Giving him the tape would be even better than telling him about his little escapade.

Chris set the camera aside and began rummaging through his lingerie. He pulled out a red silk demi-cup bra and patching panties. Then he found a black garter belt and some nude thigh-high nylons. After slipping on the garter belt and bra he sat on the bed and slid the nylons on his legs, smoothing them out after hooking them to the belt. Standing up he grabbed the panties and put them on over the garter belt and hose so he could shed them if need be.

Sitting down at his makeup table Chris applied some foundation, and light red rouge to his cheeks. Then he put on some jade green eyeliner to match his dress and some ruby red lipstick for some good contrast. Now it was time for a wig. Looking over his selection he decided on a straight, shoulder length blonde wig. After pinning it in place he looked himself over in the mirror and was satisfied with his look

After sliding into his dress he found a pair of black 3" heels to give his legs a nice long sexy look. He closed the closet door and looked at himself in the full-length mirror. 'Damn I look good tonight,' he thought to himself. He was sure it would be no problem picking up a guy in this outfit. Now it was time to turn his attention to the camera.

Rummaging around the closet again he found the tripod for the camera. After screwing the camera to the tripod he turned it on and aimed it at the bed. After focusing the camera he pressed the record button. Moving in front of the camera he began to do a sexy dance, gyrating his hips and running his hands up and down his body. After a couple of minutes of this he crawled onto the bed and wiggled his ass at the camera, smacking it in the process. Turning on the bed, to face the camera he blew a kiss at it.

Then he got up and stopped recording. Satisfied with the few minutes he had reviewed on the camera, he went downstairs, grabbed his coat and headed out the door.

After hoping into the car, Chris drove to the mall to do some shopping and then get a bite to eat. Chris was just doing some window-shopping to kill time before heading out to the clubs. Stopping in front of a lingerie store he decided to go in and pick out something new.

Her browsed for a while before a clerk asked if there was anything that he needed help with. He replied that he was looking for a sexy pair of boy shorts and a matching lace, demi-cup bra to surprise his boyfriend. The clerk was more than happy to show him to a rack of matching sets.

"You look like you are a size 10." Said the clerk.

Chris looked at her and smiled. "Why yes I am, with a 38B cup size."

"She had no idea I was a man," Chris thought to himself. Taking the lingerie in hand, he began to rub his fingers over it. It was so soft, he couldn't wait to try it on.

"Where are the dressing rooms?" Chris asked.

The clerk pointed to the back corner of the store. Chris thanked her and began to make his way to the dressing rooms. While making his way back to the dressing rooms he saw a cute guy nonchalantly looking through the racks of sale lingerie. Chris stopped at the rack of lingerie and pretended to thumb through the bras and panties.

The man was tall, about 6'4" and well toned. He had brown hair and deep blue eyes. From the looks of his tight jeans, Chris was guessing he had a sizeable cock too. Then an idea hit him.

Moving closer to the man he whispered to him, "I think those would look good on you?"

The man looked up at him in surprise. "What?"

"I think you heard me." Chris replied.

"Actually, I'm looking for something for my girlfriend." He said, blushing slightly.

"Oh, really? I saw the way you were looking through the rack, fingering the lacy undergarments." Chris retorted while smiling back at the man.

The man blushed at this. He knew he had been caught. Lowering his voice he said, "Yes, they're for me."

"Don't be ashamed honey,", Chris responded. He knew how it was when he first got into wearing lingerie, all the awkward trips to lingerie stores. "I like a guy who gets in touch with his feminine side."

Chris reached into the rack and pulled out a nice matching bra and lace bikini panty. "I think these look like they might fit you. Why don't you try them on?"

He looked at Chris for a moment with a startled look in his eyes. "You mean here, now?"

"Yes, how else will you know if they will fit?"

Chris grabbed him by the hand and led him to the dressing rooms. Looking around to make sure that no one was watching, he slipped into the first dressing room that was open with the man in tow.

After shutting the door and locking it, Chris turned and introduced himself. "I'm Christy by the way."

"Um, I'm Paul." Replied the man sheepishly. He looked Chris up and down liking what he saw.

Chris could see Paul relax a little after the quick introduction.

"How about trying those on for me?" Chris asked. "Or would you like to see me try mine on first?"

Paul stood there speechless for a moment. Before he could say anything Chris started to slip out if his dress.

"I'll take your silence as a cue for me to go first. You just sit back and relax."

Chris slipped off his dress and then his bra. His tits fell free, bouncing as they did. Before slipping the new bra on he looked at Paul who was giving his full attention to Chris now. Chris pinched his nipples so they were nice and hard before slipping on the bra. He heard Paul moan.

"You like the way this looks on me Paul?" Chris asked sweetly as he spun around.

"Um, yeah." Came Paul's reply as he continued staring at Chris' tits.

"How about you try your top on now? It's only fair."

Paul hesitated for a moment but then began to take his shirt off.

Chris sighed as his rippled stomach and chest came into full view. "Very nice."

Paul smiled at him and gingerly picked up the bra. He slipped it on like he knew what he was doing. Chris knew he had him now. After trying on the bra Paul stood there facing Chris, blushing but sporting a hard on in his pants.

"So how does it feel?" Chris asked. "It looks good on you."

"Well, "Paul came back, "it feels strange but good. I like the feel of the smooth silk on my nipples."

"I thought so. Would you like to see me in my boy shorts now?"

"Um, well, yes." Paul stammered.

Chris could tell that Paul was enjoying this. His nipples were getting hard in the lacy bra and his stiff cock was straining at the seams in his pants. If things went the way Chris thought they would, then he wouldn't have a problem much longer.

"Then I'll slip them on. But before I do I have a little surprise for you."

Paul looked up at Chris from where he was seated in the dressing room and smiled.

Chris slowly slipped his panties down inch-by-inch keeping an eye on Paul for his reaction. Paul's eyes were glued to Chris' crotch as he slowly lowered the panties. Chris lowered them slowly past his cock, the head poking out first.

The expression on Paul's face turned from one of expectant pleasure to one of disbelief at first then curiosity.

"What the hell?" Paul gasped. "You're a guy? But your tits, the hair, you look so hot."

Paul couldn't believe what he was seeing; he thought Chris was a woman. Now he was staring straight at a semi erect cock. At first he was shocked but that quickly gave way to curiosity.

Chris looked at him and smiled. "I used to be just like you but we can talk about that later. Right now I'll bet you want to see me in those boy shorts."

Paul looked at Chris and hesitantly replied, "Yes, I do."

Chris slipped off his panties and shimmied into the boy shorts. Pulling them up over his hips he tucked himself back in place and smoothed them out. Turning around for Paul he asked, "How do you like them?"

"They look great on you." Paul replied, a little embarrassed.

"How about we see how you look in your panties?" Chris said as he snatched them from Paul's hands and motioned for him to sit up.

Paul stood up and Chris began to unbutton Paul's pants. Paul moaned As Chris pulled off the jeans and brushed his hand over Paul's rock hard cock.

"Oh, looks like we'll have to take care of that. But first, slip these on. I want to see how you look in them."

Paul slipped off his briefs and slipped on the panties. He tucked himself into them as best he could but a third of his cock was still poking out the elastic waist.

Paul blushed.

"Mmm, looks like I have my work cut out for me. I better move quickly. We've been in here a few minutes and we don't want to get caught."

Chris dropped to his knees and pulled Paul's cock from the panties he had just slipped on.

"What are you doing?" Paul whispered tersely.

"What does it look like? I'm going to solve your little, or should I say rather large problem you have here." Chris whispered back with a smile on his face. "Don't you want me to?"

Before Paul could answer, Chris began sucking on his hard cock. He guessed it was at least 8" long and an inch and a half thick since he was having a hard time getting it all in his mouth. As Chris worked Paul's cock in his mouth he heard Paul let out a low moan. Taking that as his cue to continue, Chris massaged Paul's heavy balls as he continued to suck on his cock.

"Oh yesss." Paul hissed as Chris sucked him. "This is so wrong but feels so good."

He reached down and began to massage Chris' nipples as the exquisite blowjob continued.

Chris pulled off Paul for a moment and looked into his eyes. "See what you've been missing?"

Chris smiled at Paul and then swallowed his cock to the base. Paul began thrusting in and out of Chris' face as his orgasm approached. Chris sucked Paul faster, wanting to swallow his load. After a few more thrusts, Paul pinched Chris' nipples hard, gasped, and began shooting his load into Chris's mouth. Chris greedily gulped it down, swallowing Paul's hot cum.

After Paul shot his last load, Chris pulled off him and licked his lips. Standing up he kissed Paul on the lips, letting him taste his own cum. Paul kissed Chris back, slipping his tongue into his mouth.

"I can't believe what just happened." Paul said.

"Believe it baby." Chris replied "And you were good too. How about we finish getting dressed and go out to pay for theses things? I'll even pay for yours. Now get dressed before the clerks think something is wrong."

Chris slipped on his dress and pulled the tags off the bra and boy shorts he just put on. He wanted to wear it out tonight and since he had it on already there was no point in taking it off. Paul slipped off his and put his briefs and jeans back on along with his shirt.

Picking up the lingerie that Paul had taken off Chris said, "I'll pay for these Paul to avoid you any embarrassment tonight, but there is one condition attached".

"What would that be?" Paul asked.

"I'll tell you after I've bought these."

Paul thought about it for a moment and then agreed. What was the worst that could happen? He had already gotten a blowjob from a beautiful cross-dresser and loved it.

"Wait here." Chris ordered.

Chris left the dressing room and checked to be sure the coast was clear. He motioned for Paul to come out and join him. Paul hurriedly left the dressing room and followed Chris to the checkout. They reached the checkout counter and Chris handed the lingerie Paul had tried on to the woman and the tags for the lingerie he had put on in the dressing room.

"I took the tags off the bra and panties I found since I have them on and I want to buy these also." Chris said as he handed the clerk Paul's lingerie.

As he handed the lingerie to the clerk, Chris saw her look from Chris to Paul and back. She was sure they did not come in together. Chris just smiled at her. She rang up the purchase and Chris paid for it.

Taking the bag from the clerk Chris handed it to Paul as they walked out saying, "Here you go Paul, I hope you like them."

Paul blushed, sure that the clerk had heard Chris. Exiting the store into the main area of the mall Paul looked at Chris.

"Thanks for buying these for me Christy. I was beginning to get embarrassed in there by myself looking through the lingerie. I was even more embarrassed when you came up to me."

"Well you seemed to get over that quick enough. You aren't mad at me for playing that little trick in the dressing room are you?" Chris asked as he began walking to the food court with Paul following.

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