Cathy's Adventures

by

Cathy Evans

 

Cathy, chapter 2

Further adventures with my Mother-in-Law........

"The OTHER story!".............

In my first story about my life with my wonderful Mother-in-Law Vicky, I mentioned there were a few times when she made reference to having seen me in my wife Cindys wig - or the times when Mom herself participated in the fun and games. Yes, it's true - I admit to allowing my girlfriend/wife to dress & make me up , it sort of parallels my fetish of hair or just about anything that feels soft and sexy against my skin. I can't help it - I just CRAVE the feeling such things provide. In the same vein, the feel of makeup on your face is indescribable. Why is it that the accoutrements of manhood are so uncomfortable and dreary - while those of the female feel so damn GOOD? It's just not fair - it happens this way only in the species homo erectus (MAN) - and in no other. In any other species, the male is the more beautiful and colorful. Why should women have all the best? Anyway - Mom must have read this little quirk of mine right away, certainly before her daughter did. Let me explain...

I mentioned in part 1 of my story that during the time Mom stayed with me when Cindy left, that she had talked a lot about the fun she had seeing me wearing one of Cindys wigs . That little episode had occurred early in our relationship. During the time Cindy and I went together she had very long beautiful brown hair, almost to her waist. I reveled in it, having some- how developed this fetish for the feel of soft hair when I was little. I was constantly running my fingers threw Cindys luxurious mane; touching it; whatever, just constantly playing with it. Cindy seemed to enjoy it herself - she never complained or let on that it bothered her. I especially enjoyed walking up behind Cindy and hugging her - then, slideing my hand under her hair from the front and running it to the back of her neck, I would lift Cindys hair up so I could kiss and nibble on her neck and ears as I casually let her hair fall, totally covering my head in the silky soft mass. It was so long that my head could not be seen at all! God I loved doing that. Mom saw me doing it a few times (I was totally at ease at her seeing me make love to her daughter), and smiled brightly and in retrospect, knowingly about what I was up to. She also - I found out during her stayover - had seen Cindy doing some of her tricks with her fabulous hair. Mom told me, as we were lying in bed together after a particularly good fuck, that she had been watching one night when Cindy stripped down to a very sexy black bra and panties, then took her brush and stood in front of me, swaying sexily and brushing that beautiful hair. She would first bend her head slightly and twist to one side so all the hair would fall that way when brushed, then snap her head back and do the same on the other side. Then she would kneel on a pillow in front of me on the couch so I could brush it for her. I always liked it best parted on the side so the hair would sweep across her face, partly covering it when she moved, something like that famous actress from the 40's.

After a while Cindy would have me stand up so she could unbuckle and remove my pants as she stared into my face and let that unbelievable hair fall slightly across her cheeks; then grab my dick and gently pump it as we kissed softly. When Cindy knew I couldn't stand any more, she would push me gently down on the couch and kneel on the pillow between my spread legs as she smiled up at me and swung her head to the side so all her hair fell over one shoulder. Then she would lean forward so the mass of silkiness would brush over my legs, groin, and belly. She would keep this up for maybe 10 minutes or so, or until I was begging her to suck me. When she was ready, she would sweep her hair from my knees up till it completely covered my balls and dick, then gently open a space in the silky mass so my dick could pop through - right into her warm mouth. Incredible. Cindy was a master of the blowjob. She usually had me squirting into her mouth in 5 or 10 minutes, unless she wanted to torture me a little! She was careful not to let to much semen spill out of her mouth into her hair since it would make knots that were a BITCH to comb out! Thinking back- the thought that my Mother-in-law had been watching her daughter performing this little trick was incredibly erotic. Mom proved she had witnessed the act by performing the exact same sequence of events during her stay with me!

Subsequently, Mom would beam and smile with a little wink whenever I would start to play with Cindys hair or Cindy would begin to tease me with it. There was one time when Cindy was getting playful, much to the delight of both Mom and me, and she leaned up close to my face and lifted her hair over my head and let it drape down over the side of my face and over my shoulders. I was trying hard not to get a massive hardon in front of Mom, but lost the battle when Mom smiled that smile that lit up the room, and stepping up to us, used her fingers to arrange Cindys hair over my head, pushing it softly around as she cooed "Don't you look wonderful! With a little makeup you'd look like Cindys sister!" All the while Mom was talking, she was running her fingers through "my" long hair, patting it gently around my head and shoulders, and generally arranging Cindys hair as much as possible like it was my own. I was getting incredibly hard from the attention Mom was giving me and nearly blew my load when she "accidently" let her hand brush my bulging pants. She never changed her expression in front of Cindy, but as Cindy turned her head to pull her tresses off me (much to my regret) she gave me a sly wink! That's when she "jokingly" giggled, "You know Cin, someday we're going to have to put some makeup and one of your falls on him just to see if he'd be as pretty a girl as you! What do you think hun, would you do that for me?" I was trying my best not to look too interested in the proposal, while secretly trying to visualize the process. Cindy was laughing at the idea - she thought it would be fun and began brushing her fingers lightly around my face as if she was applying makeup, saying,'Let's see- a little mascara, eye shadow, pancake - I know just the colors for him- and my new fall would look very nice on him in place of my hair! - yeah, he'd look adorable Mom! What do you think babe?..could we do it?" I put up as vigorous a protest as I could manage under the circumstances but I think they both caught on to me. Then, not long afterward, Mom and Cindy had their fun. At the time, I was 18, Cindy 17, and Mom about 38.

We were all sitting in the TV room (no pun intended!) watching a movie and generally enjoying each other. I was of course playing with Cindys hair, as Mom watched and smiled approvingly. We were watching a thriller movie called Dr. Jeckle and Mrs. Hyde, a takeoff on the classic, the difference being that instead of changing into a murdering monster- this Dr. turned into a very beautiful woman! Mom commented on the feasibility of such a transformation, acting very excited about the possibilty. Cindy had a very mischievous look in her eyes and abruptly stood up and asked if anyone wanted a soda. Mom and I said no and returned to discussing the idea of such a thing as being able to change your sex any time you wanted. Mom was very intent on stating that she thought it would be a wonderful thing if men and women could experience life as the opposite sex on demand. I noticed she was looking over my shoulder at the time with a sly grin on her face. I turned around to see Cindy standing in the doorway; her new fall draped over her hand as she brushed it softly into a pageboy style. "Well Mom, suppose we give it a try!", as she stared into my face. "Oh no, wait a sec here", I protested, "I never agreed to this!" "Oh come on!", Mom jumped in, "it'll be fun! Nobody will know but us! Come on..PLEASE?" " NO!", I repeated, though not very convincingly I guess because Mom shot right back, " I bet Cindy would make sure you're relaxed when we're done". Cindy took the opportunity to brush the long fall over my face (dirty pool!) and whispered teasingly, "If you don't let us - I'll cut my hair off real short!" No way I could hide the horror of my reaction to that possibility! "OKAY.. OKAY!", I said quickly, "but if either of you EVER tells anyone about this I'll die!"

Cindy and her mother squealed with anticipation and dragged me into Cindys room. "Let's see....Mom, you two are about the same size.... you'll have to change clothes with my sweetie. I'll start on the makeup!" "Come on, Cathy - get out of those clothes!" "HEY COME ON WILL YOU!, GIVE ME A BREAK WITH THE CATHY CRAP!" I protested. Cindy just giggled. "Oh don't get mad....I'm only playing!....this will be FUN! And besides - if you're going to look like a girl, you need a girls name ... and cathy is so cute and girly I think that's what we'll call you!" Mom left to go to her room to pick out some clothes for me as Cindy began to undress me, giggling and fussing all the while. When I was naked, Cindy handed me a robe to put on while she worked on me, "can't have my MOTHER see my boyfriend NUDE, now can I?!" she giggled. She sat me down at her dressing table and explained how the makeup and stuff was applied, then showed me how her new $100 fall fit. In case you didn't know, "falls" were very popular in the 60's to give women extra hair for the styles that were popular then. A fall was a small cap of lace material- the same as used to make full wigs- about the size of a skullcap. The hair, which could be of varying lengths depending on cost, was sewn into it. They usually had 2 combs attached to the top sides of the cap to attach it to your hair and 1 or 2 long lengths of hair on each side which were supposed to be crossed over and clipped behind the ears which would hide the line of the cap in the front. The total effect was that of a thick mass of hair hanging down the back of the head like it was brushed back from the front. Combined with the usual bangs of the period, the look was very convincing and sexy swinging down the girls shoulders. Cindy had a good girlfriend who worked at a local salon who got her the fall at a very good price - it cost much more than the $100 she paid for it. It matched Cindys (and MINE!) haircolor perfectly, and was very thick and reached to just below the shoulders. Cindy usually wore it with her own hair pulled back on the sides with combs, feathery bangs over her forehead, and the fall fixed to the top of the area where her hair gathered to fall down her back. With the fall attached, the thickness of her natural hair was accentuated and looked incredibly sexy but sweet if you can follow what I mean. Sort of like a really sexy schoolgirl! Anyway, Cin had a special piece of foam that attached under the falls cap that gave it more height like it was teased up natural hair, it was in this way she intended to do my hair.

Just then Mom came back into Cindys bedroom, all giggles and fluttering about. Unlike what I, and Cindy, had expected, she was all dressed rather than carrying the outfit she had picked for me. "Mom...what are you doing.. I thought you were going to pick something out for Cathy to wear?", she asked. Mom was wearing a 2 piece suit that she knew was one of my favorites on her - the last time I saw her wearing it I had mentioned how great she looked in it. Her reaction to my statement was to stroll slowly up to me and give me a very tender hug and kiss on the cheek, looking into my eyes and saying "You are the sweetest boy I have ever met, John, such a gentleman. I'm glad I said just that to your Mom and Dad the other day. Cindy is a very lucky girl, I hope she appreciates you. Thank you." Then she kissed me again, a little more sensually and just off my lips. Anyway, Cindy said "Mom, you were supposed to pick something out for him!" Mom just smiled and replied,"listen....YOU said we were to CHANGE CLOTHES...YOUR words, right? So...In order to CHANGE clothes - we have to be WEARING them! If I'm going to be putting on clothes Johnny just took off..it's only fair that HE puts on the clothes that I just took off, right John?" Mom smiled that knowing little smirk at me again - she knew I liked that outfit. "Besides, Johnny likes this suit alot...don't you sweetheart?" Trapped! "Uh...yeh Mom, I do....I mean I like it on you." "Great!, it will look terrific on you too! Not to mention my undies!" "What.. you mean you want to exchange underwear too?" I blurted. "Of course!", Mom replied, "we are supposed to become each other, right? That means everything as far as I'm concerned. Holy shit, this was getting kinky! My mother-in-law wanted to put on my underpants and everything (I wondered if she would notice the wetness from my excitement), and I would have to put on her warm panties and things! "Come on, Cindy, hurry up, I can't wait to see him all done up!", Mom squealed. " I'll polish his finger and toe nails while you do his makeup. Come on sweetheart...out of those clothes!" Mom said as she began to undress, staring intently into my face as we both peeled our clothes off. Cindy just sat and laughed watching the fun. Mom stepped close and said very softly, "everything but your undies, honey, I want you to put mine on when they're still warm from my body." I nearly freaked.

Cindy spent nearly a half hour putting on my makeup. "I want to see how you could REALLY look done right...not just like a clown" she said. Mom agreed. "Right honey. Be as realistic as you can". Truth be told, I was getting into being fussed over like this, and the makeup - especially the extra glossy lipstick - felt really nice. "DONE!", Cindy shouted, "what do you think, Mom? Doesn't he look fabulous!" Mom looked very pleased with the job Cindy had done. "Okay...now you go done to the TV room and put on a nice nightgown for later (winking at me), and I'll finish with Johnny!" Oh boy.. this was getting very interesting! "I don't want you to see yourself until I've finished dressing you and doing your hair, Johnny....can you hold out.. or do you need a hand to settle yourself down" Mom whispered. She appeared to be pretty aroused by this whole deal. I opened my mouth to answer her outright proposition...but nothing came out. I didn't have to say much as it turned out..Mom just said softly "Okay honey, don't be embarrased...this is all in fun. I never wanted you to be uncomfortable with this....I'm laughing WITH you..not AT you" and then kissed me softly on the mouth. "This is our little secret...I promise not to say anything to anyone." She took my hand gently and led me to the dressing table and sat me down. "Just let me fix your hair... then I'll see what I can do about your....problem".

It took Mom about 10 minutes to brush my own hair back and clip it, leaving very convincing bangs which she curled lightly across my forehead. Then she took the fall, lift inserted for some height, and placed it on the back of my head,working the fastening combs into my hair. It hurt a little when the combs took hold,but it was bearable. Then Mom took the 2 side pieces and passed the over the front of the fall, almost like a headband, and tucked the ends behind my ears. I must say, the feel of long silky hair on your neck, especially when it is your own and moves softly when you turn your head the slightest bit, feels incredibly sexy. When it was firmly secured Mom whispered "Be very quiet and stand up a minute." She slipped my shorts down and took my dick in her hand! "I don't believe this is happening" I thought, "my girlfriends mother is going to jerk me off!" Mom looked into my eyes, she was definitely aroused, and whispered hoarsely "As much as I want to, I can't take you in my mouth....maybe someday...but now is too soon. You'll have to be satisfied with this", and she began to stroke me up and down. "I'm sure Cindy will blow you later." With those erotic words in my ears I shuddered and blew a load of come into Moms cupped hand. She stared down at my dick as she milked it shooting into her hand. When I was finished shooting, Mom looked into her overflowing handfull of warm come and raised her hand to her mouth. Sticking out her tongue, she licked a generous portion of my semen into her mouth, then looked into my eyes and whispered "This is for the compliments you gave me." and swallowed my come down. She took the rest and let it run out of her hand into her pubic hair and smoothed it in and around her vagina. I was going nearly crazy I wanted this woman so badly. I attempted to kiss her shining lips but she pushed me gently away. "No honey...not now...Cindys going to get suspicious. We have to get dressed.

I dressed Mom in my clothes - chino slacks, loafers, white turtleneck under a madras plaid shirt. I must say she looked very nice. I took some hair jell and combed Moms full hair back into what we called a D.A. back then. She really fit the part then. Mom was very gentle putting her still warm from the body bra and panties (wet crotch!) on me, the showing me how to roll on her stocking and clip them to her garter belt. God... the erotic act of having a woman putting her personal garments- still warm and smelling of her body- on you, is overwhelming. I couldn't help getting another erection "You're making this very hard for me, you know that?" Mom giggled. "No.... YOU"RE making it HARD ON ME!" I answered. Mom finished helping me into the black wool straight skirt, white satin blouse with a big bow at the neck, and short black wool jacket top of the suit. She clipped a pair of her best rhinestone and pearl earrings onto my exposed ears, and looped a matching necklace around my neck. She then bent down to help me step into a pair of her low (2") heels to finish the outfit. I couldn't believe how terrific the silky clothes of a woman felt against my skin. "One final brush and you're done", Mom whispered, and stood behind me to brush out my hair.(I mean Cindys hair). That done she stepped back and stood looking at me, shaking her head. "Well...take a look in the mirror, gorgeous." Mom said.

I thought she was making fun of my appearance until I walked unsteadily over to the full length door mirror and stared in shock at the reflection of a very pretty teenage girl. "I LOOK GOOD!" I said to myself. I was standing still - staring at myself and smiling, as Mom walked up and took my hand. "Come on silly...I don't blame you for staring - you do look terrific....lets go down and show Cindy my new daughter."

We walked down the stair holding hands, for emotional support as well as stability for the high heels. I could see Cindy brushing that wonderful head of hair as we approached the TV room. As soon as Cindy saw us -ME- she jumped up off the couch ands rushed over to us. "What do you think, Cin, doesn't he look fantastic?" Mom said. Cindy just squealed with delight and jumped up and down, "Oh Mom....you did a terrific job! WOW...I DON'T BELIEVE HOW GREAT YOU LOOK! CAN WE DO THIS AGAIN?...PLEASE? COME ON... I'LL BUY SOME CLOTHES FOR YOU AT THE MALL...SOMETHING REALLY SEXY AND FEMININE! I'LL SEE IF I CAN BORROW A REGULAR WIG FROM ANDREAS'...HEY..MAYBE SHE'LL HELP WITH YOUR MAKEUP AND HAIR!!! OH WOW..THIS IS GOING TO BE UNREAL! "WHOAAAAA, WAIT A MINUTE!" I shouted. "What are you talking about, doing this again next week? This is it! You said once, right Mom? And what is this about bringing Andrea in on this....are you trying to ruin me? All she would have to do is mention it to anyone and I'b be the laughingstock of the school!" Cindy calmed down a little when she realized how upset I was getting. "It's Okay...Andrea wouldn't dare say anything. I happen to know she's been taking money from the salon. I don't think she wants to go to jail, do you? Besides, she's a professional....if Mom and I can make you look like this...what do you think she could do?" Mom interrupted Cindy and said softly but firmly, "Cindy...stop it now. you're getting carried away. Johnny said no..leave it alone. I think it's his decision if he wants to try this again (staring hard into my eyes- for a sign?). It's your decision Johnny" Mom said softly. Cindy turned to me and hugged me tightly, brushing back my now long hair with her hand like I did hers. She whispered softly and passionately as she kissed me lightly all over my face and neck, again lifting my hair and kissing my neck as I did to her daily, "see how good it feels baby...I'm getting so turned on I can't stand it. Please baby...do this for me next week again - or when ever I ask you? Please....this is such fun! Mom....tell him...tell him what a turn-on this is....come on babe - it really makes me horny!" And with that Cindy unbuttoned my skirt (Jesus..now I'm starting to think screwy) as she kissed my face all over and pleaded with me. "Take off your jacket" she said, and helped me slid it off. "Is it Okay Mom?" Cindy asked,,never taking her eyes off me, "Do you mind?" "No Cin, I don't mind.. he needs it" "WHAT'S GOING ON NOW?" I asked myself, "WHAT ARE THEY TALKING ABOUT?" Mom stood facing me,leaning against the door jamb, arms crossed in front of her, smiling broadly as Cindy slid the skirt down my legs,(Jesus that feels good!) leaving me wearing nothing but shoes, stockings, panties, ruffled blouse, and bra. As Mom stood watching intently, Cindy slipped my panties down, allowing my fully erect dick to pop right into her face. She took a handfull of her hair and brushed my throbbing dick and looked up at her Mom for approval. Mom glanced down at my dick covered in her daughters soft hair, her hand slowly moving up and down, and nodded. "Go ahead Cin, suck it"

Holy shit! this is too much! Think of it...here is a mother..watching her daughters hand work over my rock-hard..I'm dressed like a girl- in the Mothers own clothes!...the mother is wearing MY clothes....and now she is telling her daughter to go ahead and suck my dick!...while she watches!!

Cindy smiled at her mothers words and kissed my dick all over until it was coated with bright red lipstick (I wished it was Moms!), then sucked it hard into her mouth, her long hair swinging as she pulled my dick into her mouth. I had one hand tangled in Cindys hair and the other I held out to Mom. She smiled and walked to me and took it in her hand and squeezed it, then leaned close and kissed me softly on the mouth, flicking my lips with her tongue once or twice. Then she stood next to me and looked down, watching and smiling as Cindy sucked me. She put her hand behind Cindys head and moved her head in and out on my dick. "That's it..that's enough! I'M COMING! OH SHIT.. OH GOD...HERE IT COMES!" Mom dropped to her knees next to Cindy, and smoothed her hair before locking her fingers into it. Holding my butt with her other hand..she began ramming her daughters face over my dick, whispering hoarsely "SUCK HARD..SUCK HARD..HERE IT COMES BABY!..OPEN WIDE!" Incredible! Mom took my throbbing dick in her hand and began jerking me off, pumping furiously, still urging Cindy to suck hard, AAAAAAAHHHHHHHHHHHH... I started shooting streams of warm creamy come into Cindys open mouth as her Mom pumped my dick and guided the squirts into her daughters mouth.

"UUUUUHHHHHHH!...UUUHHHHHHHH!....MMMMMMMMMMMMMMMMMMM!..MMMMMMMMMMMM! Cindy was moaning as her mouth filled to overflowing, the come dribbling down her chin and neck. Mom just kept on pumping my dick into Cindys mouth. "MORE...GIVE HER MORE!..GOD!...I WANT SOME TOO!" Mom pulled my dick away from Cindys mouth and wrapped her lips around it as she continued to pump it up and down. I lost it and popped another load into Moms sucking mouth. Cindy stared in amazement as her mother sucked my dick into her throat, then she relaxed and looked up at me and smiled, then swallowed the load in her mouth, as she ran her fingers through her moms hair. "Suck his dick Mom, oh wow..this is so wild...I can't believe my mom is sucking your dick!"

A few minutes later, Cindy and Mom had drained every drop of come I had in my body, I think. They looked up at me and Cindy asked, "Well... whats the answer?....want to dress up for us again next week?" I couldn't manage anything but a groan..I was totally wiped. Mom smiled at Cindy and said happily, "I think that was a YES!"

As they both giggled with delight, Cindy took my now shrinking dick and gave it one more wet, slurping, suck. Then she squeezed out a little more come and held it to Moms mouth.."Here Mom....this belongs to you!" and pushed my dick into Moms hungry, sucking mouth with a smile.

During the following week, Cindy and Mom were extremely affectionate with me, more so than usual. Mom took every opportunity to hold my hand or kiss me - innocently enough - on the cheek. But neither could hide the mischievous laughs or double entendres when discussing the coming weekend. Andrea - I soon learned - had agreed eagerly when Cindy approached her with her idea. Apparently, she had had some experience with the subject - her boss was a cross-dresser (WHO KNEW!) - and she had frequently helped him with his early attempts at feminization. She related to Cindy and Mom how turned on she got - molding a man into her image as it were. I heard her explaining that this was the way she got extra money from the register whenever she wanted it - she had her boss in her pocket! At any rate, Andrea told Cindy that she would bring over 2 or 3 different wigs, and a few falls, along with some hair accessories to perfect the look when worn - bands, clips, combs, etc. Mom told her that I preferred dark hair, so Andrea would only bring dark brown/brunette hairpieces. She also would supply the makeup she needed, saying she wanted Johnny to look as fabulous as possible. She was amazed and very turned on when Mom showed her the Polaroid she had taken of me (surprize!) when dressed and madeup. The three of them couldn't wait until Saturday to arrive for the fun! Actually, I was a little excited myself! Mom and Cindy had gone shopping for some "pretty outfits for a pretty girl" - as Cindy put it - but they were not letting me see what they bought until Saturday. They did show me a pair of high heels they bought me; black patent leather, 3 inch heel, open toe "slingbacks". Very sexy. They also showed me the jewelry they had picked for me; 3(?) pair of earrings, a black velvet choker, 2 necklaces, a few bracelets and rings. I was getting very nervous about how far they were taking this game! I went to see Mom on Wednesday while Cindy was at school - she wanted to remove all my body hair with a cream (not that I had much anyway) - and wanted it to be a surprize for the girls. The entire time I was there,Mom had this really devilish grin on her face. I knew then that this was not some spur of the

moment idea - she had a thing for males in feminine clothes and had egged Cindy on about it for a while. After I was done and showered the hair off, I felt really horny from Mom caressing me. She had rubbed me down with a skin moisturizer to soften my skin and keep me from itching, since I now had NO hair ANYWHERE on my body. Mom hugged me tightly after she was through and whispered urgently "Come to my room. We still have a few hours before Cindy gets home - I want you to put on my panties again for me! It makes me so hot seeing you in them! And my bra, stockings, and a slip too, OK? I'll suck you for a while if you do this for me!" WHAT COULD I SAY! "OK Vicky, if you really want too." She was breathing hard as she pulled me to her room, so I guess she meant it alright!

As soon as we got to her room, Vicky opened her dresser and removed a bra, panties, stockings and garter belt, and a lacy black slip. "Here honey, I want to watch you put these on for me!" Mom whispered. As Mom sat on her bed, I went about putting the silky items on. "God these things feel GOOD with my hair gone!", I thought to myself. Mom sensed what I was thinking and said softly, "Some difference with all that hair gone isn't it? Come over her and lay down with me." I walked to the side of the bed and layed down, Mom immediately taking me into her arms in a warm hug. "I can't wait till Saturday, you are going to look so cute when we're done - even better than the other night. It makes me so hot seeing you in my clothes!", she said, "but that slip is in my way", as she peeled the slip up to my chest,"panties too", and slid them down off my legs. "That's much better", she whispered, and then slid down so her head was on my belly very close to my dick. Her soft hair felt like silk on my now hair-free belly, as she gently ran her fingers over my dick and cupped my balls, then lifted her head enough to lightly kiss my dick all over, then slid further down to lick my balls and suck each one gently into her warm mouth. "So much better without the hair honey", she said then gave my throbbing dick a long lick from the balls to the tip, then closed her mouth over it and sucked hard. After a few minutes of this, I was getting ready to come. Mom must have felt my balls throbbing, and popped her mouth off my dick and slid up my body, stopping to suck my nipples for a minute as she held my dick in her hand and rubbed slowly. She reached up and kissed my deeply as she straddled me, and rubbed her breasts against my chest. God, this was the hottest woman I had ever known! Then she reached back between her legs, grabbed my dick again, and as she sucked my tongue into her mouth slid my dick into her warm, wet pussy! An involuntary "UUUUUHHHHHHHHHNNNNNN!" escaped from my throat as I realized I was in Vickys pussy, I couldn't talk since she was still sucking madly on my mouth. Vicky continued to rock back and forth onto my dick for a few more minutes until I was throbbing again, then took her mouth off mine just enough to whisper "come in me honey!" before mashing my mouth again. No sooner had she finished saying that than I began to come harder than I have ever come before, shooting spurt after spurt of come into Vickys insides.

As I was moaning "uuuuhhhhh uuuuuuuuhhhhhhhhh!" as I shot my load, Vicky began to shake and ram herself harder over my spurting dick, whispering throatily "ooooooohhhhhhhh oohhh baby - I'm commmmming, ooohhhhhhhhh!", then sat up straddling my dick until I was in her to the base of my dick and the kept it all the way in and wiggled side to side as I continued to fill her with my come. "Ohhhh, your come feels so warm inside me" Vicky whispered as she bent down to kiss me again. She laughed softly as she kissed my neck "you come MUCH harder when you're wearing panties and things honey - I knew it excited you. Don't be embarrassed - I told you before - I don't think you're a sissy or anything - I'm glad you feel comfortable enough with me to let me do it to you!" Then she slid down again and took my now shriveled dick back in her mouth and sucked it clean of its coating of come - mine and hers both. "We are going to have a terrific time this weekend", she whispered, "wait until you see the outfits we got you. Andrea stopped by last night to show us the wig she picked out for when we go out to eat - it's GORGEOUS - you'll look so GREAT in it!" she said excitedly. "Oh, don't worry about that - no one will suspect a thing when Andrea and Cindy are through with you! Oh crap, you better go now - Cin will be home soon", as she kissed me warmly, "get dressed......YOUR clothes this time!"

My legs were a little weak as I walked to my car, for more reasons than one! What had I let myself in for? Now they wanted me to go out to eat in drag! "Well....let's see what happens...", I thought to myself.

Saturday morning............

Saturday morning, Cindy stopped by my house. She was sitting in the kitchen with my mom talking when I walked in from my room. "Well, its about time you got up, Cindys been telling me about the date you have planned for tonight", mom said. Cindy had this devilish gleam in her eyes as I nearly spit up my coffee and gaped at her with my mouth open. "SHE WHAT!", I almost shouted. "No....YOU DIDN'T!" I said to Cindy almost pleadingly. "What's the matter with you?", mom asked, "can't she talk to me anymore?" I glared at Cindy - who was almost beside herself with suppressed laughter. "I think it's wonderful of you to take Vicky with you to the theater," mom said with a look of puzzlement, "why wouldn't you want me to know that?" Cindy just giggled "Oh Carol...you know how he is...doesn't want everyone knowing what an old softy he is, being nice to my mom and stuff". Oh jesus, I thought,I don't know if I can handle this. Cindy popped up and bent over to give my mom a light peck on the cheek, "gotta go Carol....me and mom have a lot to do to get ready for tonight!" She swayed up to me and kissed me lightly on the mouth, "she you about 6 sweetie? We want to get good seats for the show!" Then she turned and walked to the front door, looking over her shoulder and yelling "Bye Carol!" As she walked out of sight of my mom, Cindy stopped and turned around. She flipped all that hair over one shoulder and swung it back and forth as she stared into my eyes and sucked one of her fingers into her mouth. She whispered so mom couldn't hear, "Tonight babe......I have something SPECIAL for you to wear." My dick was hard as a rock as she smiled and opened the door and left. Mom walked up behind me and put her hands on my shoulders. She said "I thinks its sweet of you to take Vicky with you tonight honey....she must get very lonesome being alone all the time" "You can't imagine!", I thought to myself. "Yeh..I guess ", I said to mom as I went to my room to settle down.

Saturday night...........

I drove up to Cindys house just before 6:00 - a nervous wreck. I had no idea what was going to happen tonight, other than what Cindy and Vicky had already told me. I didn't know what to expect now that Andrea was involved. Andrea was a very hot number, the kind of girl all the guys wanted to be with for fun but not the marrying kind, you know? I always thought she was too much for any one guy to handle - but I had my fantasies about her too, since I knew her from school as well as through Cindys friendship. She was about 5'7" tall, built like a playboy bunny - with a smile and manner to match, and very thick shoulder length red hair.....real red, not from a bottle. She was drop-dead gorgeous - and knew it - and took every advantage of it to get what she wanted. A bat of her green eyes and toss of that deep red hair and any guy in the world would be like putty in her hands. Well, anyway - to continue.

I knocked on the door, and it opened to reveal Cindy and Vicky and Andrea with the biggest, most evil smiles I had ever seen . Cindy pulled me through the door and kissed me passionately.....she was hot already. Next Vicky hugged and kissed me...and I was a little stunned when Andrea - who waited in the background for a minute - swayed up to me like a hooker, put her arms slowly around my neck, and gave me a long, lingering kiss. I was waiting for the fireworks to start from Cindy but - surprisingly - all she did was laugh! Cindy said "Hey Andrea...he's taken...remember?" Andrea still had her arms around my neck and was VERY close and staring devilishly into my eyes and said " Yeh..I know...but in a few minutes he's going to be all mine for a while......aren't you sweetie? " Then as Cindy and Mom laughed, she put her hand on my bulging pants and rubbed my erection and whispered "glad to see me baby? I'm going to make you beautiful....you're own mother won't recognize you!" Cindy pulled me away from Andrea for a minute. "DOWN BOY!", she laughed, "can I trust you with this she-devil? Andrea...leave some for me, Okay?" ????? "What now?", I thought. " Okay... you go with Andrea..Mom and I are going to get dressed. I can't wait to see you later!!! Have FUN!!!!", Cindy said with a giggle as she and Mom walked to Moms room and Andrea began dragging me to Cindys room.

As soon as we entered Cindys room, Andrea locked the door and threw herself into my arms again. "I had no idea you were so wild Johnny...I never should have turned you down that time you asked me for a date in high school. Just think what you've been missing!" DAMN!...I forgot all about that! "Forgive me, baby...I'll make up for that mistake later....but FIRST!... out of those clothes!" I don't think I ever got out of my clothes so fast. I stood in front of Andrea as she walked around me, examining..touching.. " Wow...when did Cindy smooth you? That's GREAT...You'll look even better!"

"Vicky did it", I said, "the other day...she said she wanted to surprize Cindy" Andrea gasped in surprise, VICKY .... CINDYS MOM!!! Oh WOW!...what a TRIP! Oh God.. I'm getting so horny!" Andrea pointed out some boxes on the bed. "Open the small one first..you can put on your undies while I do your makeup and put on your wig" The box opened - I stared at a set of black silk tap pants ...a pair of slinky high cut panties(these to hold my dick) a black lace garter belt with sheer black stockings with little black dots all over...a black lace halter bra...and...a pair of silicone breast forms.

"Holy SHIT!" I gasped, "are they kidding?!" Andrea put her arms around me from behind and whispered, "I TOLD you baby...this is for REAL! Come on.... I'll help you." Andrea helped me into everything, oooooohing and aaahhhhing each time she fitted a piece. "Put on your heels...I don't want you to get a run....we only bought one pair....the damn stockings were 12 bucks! Plus, it'll help you get used to them." She held my arms as I stepped into the sexy heels they showed me earlier in the week. "Wooooowwwwww!" she whispered "great legs!" I was blushing three shades, but I loved it! "Makeup time!" she giggled, "sit here"...indicating the makeup table. " Okay...with your coloring and hair .... let's see ... peach foundation; coral blusher; charcoal grey, light gray, and pearl shadows; black black mascara ....Damn..I wish I had eyelashes as long as yours!; and glossy deep red lipstick. Here goes!!" I watched the progress in the mirror as she expertly applied my makeup. I couldn't believe the difference as she progressed! " Oh God..I LOVE this!" Andrea was getting hotter by the minute. " Oh shit...baby, I can't wait.." She peeled off her panties, pulled mine down and off and straddled my legs, wrapping hers around my waist. "Put your arms around me!" she said as she slid my dick into her pussy. "Ooooooohhhhh...that's niiiiccccceee!" she whispered. She rocked back and forth as a held her around the waist. Just about the time she finished with my lipstick..completing the makeup...we both came. I shot spurt after spurt into her as she moaned and forced me in as far as I could go. "Ohhhhhhhh...Cindy was right!....you DO come in quarts!" She lifted off my dick and got to her knees between my legs, then dropped her head onto my dick...her gorgeous red hair covering my lap. A dream come true...I shot another load into her mouth! "Uummmmmmmmm! Muwww! (more?)she gurgled, and sucked harder than I had ever been sucked. I shot 3 or 4 more squirts into her mouth which she swallowed happily, then sat back on her heels and grinned up at me, " UnREAL! Twice in 5 minutes! I envy Cindy...and I'm glad I made this part of the deal...and I get you again later. I'm not planning on leaving Cindy and her mom ANYTHING!" I gaped at her happy face as she whispered, "Baby..in that box over there is a wig worth roughly $750 dollars. I chipped in another $50 for your undies, plus the makeup. I don't come cheap. They agreed to let me have you as much as I wanted as payback, and baby...I want you alot!" She kissed my now-soft dick and pulled my panties back up and arranged everything. She stood up and walked over to the bed, taking the top off a large box. "I don't want to mess your hair too much so you can put your dress on first". She pulled about the most beautiful dress I've ever seen out of the box and held it up in front of her. "LIKE IT!??? You are going to look FABULOUS in this!" Andrea was holding up a slinky black cocktail length dress. It had a scooped neck cut almost to the ends of the shoulders going into long sleeves, the back cut almost halfway down (THATS why the strapless bra!),and a skirt with 3 tiers of large ruffles that would barely cover my ass! I could hardly speak...I was supposed to go out in that?! I tried to joke my way out of it.."Uh..gee Andrea...won't I be a little OVER dressed for Micky Ds'?" Andrea grinned and walked up to me and held the dress up to me and appraised how it looked.."Who said anything about Micky Ds'? We're going to the CLUB for Ladies Night Out, silly! You're going to knock 'em OUT!"

I nearly fell on the floor...the CLUB for ladies night..holy shit... just about every girl I knew went to the CLUB..SOMEONE would recognize me! Andrea could read my face.."Relax honey..come'ere.." She stood next to me in front of the mirror.."Look....does that face look like Johnnys?...and those legs....do they? And believe me...once I get that wig on you.... well..you'll see! Speaking of which...sit - time for the finishing touch!" She brought the wig box over and put it on the makeup table, the reached in.."Ready?"...and lifted out....nah - that can't be a WIG can it? She shook the wig form in front of my face..the dark brunette hair bounced like silk floating over itself. It was stunning and took my breath away.

It was all soft waves, slightly tapered for fullness, and reached about to the middle of my shoulder blades (about to where the back of my dress would be, and very, very thick and shiny..it would be very full without being teased at all, and you could see lifelike scalp through the hair as it fell in natural parts, further enhancing the illusion of real hair.

Everything that turned me on about hair - this wig had...in spades. "Well? how do you like it?" she asked softly, "does it suit you?" I shook my head yes and reached out a took it from her as she giggled "I knew you would". I held it and ran my fingers through the silky waves, shaking it slightly to see it slide over itself like Cindys silky tresses; Andreas too. "Put it on!" I whispered. " Slip into your dress first..then your hair goes on" she answered. I didn't hesitate again, and she helped my into the dress and zipped the back up." I couldn't get out of this dress if I tried!" I thought.

Andrea stood back a bit and admired how the dress looked on me. I looked in the mirror and....".jesus..that's not me", I said. "I told you" she answered, sit...hair time baby" As I sat, Andrea explained that this was a professional wig like they used on stage and in movies, and would be undetectable once it was on. She showed me how it had a band of flesh colored thin latex all around the base and 3 locking combs inside to hold it securely during action scenes. The band would be glued to my scalp with spirit gum after the combs were locked into my own hair, leaving no trace of a false hairline! The hair thinned out a bit near the band just like a real head of hair and was almost impossible to knock off. Andrea looked at me and whispered, "Okay.. this might hurt a little..but I have to make a few places to lock the combs into" as she put a very tight nylon band around my head and slipped it back, pulling my hair and skin back, brushing it tight and using clips to make 3 large curls on either side and back of my head. "Oww!" I said. "I'm sorry baby, I said it might be uncomfortable..but look at your face now" I looked in the mirror to see a totally unrecognizable face looking back! Pulling my hair and skin back had been like a face lift, changing the shape of my eyes and pulling my cheeks up high like a girls. "Damn!" I whispered as she laughed softly. "It will be worth it when its on baby. Turn around, I don't want you to see it until its finished." Andrea pulled the wig down over my head and locked the combs into the curls she made. It hurt, but after Mom did it with Cindys wig I was used to it. "Almost done", she whispered, "I just have to glue the hairline band now" She worked her way around, glueing the band to my skin around the forhead, over my shortened sideburns and around my ears, and across my hairline across the back of my head. "Okay, tilt your head back and shake your head....like you were brushing your dick like Cindy does", she laughed. I did, and sure as hell it wouldn't fall off. "Put your hands under your hair in the back...see how it feels like long hair growing naturally?" I did..and it did! "It looks GREAT!.. now, don't get carried away!.....run your fingers back through your hair from your temples like you do to Cindy.....isn't it amazing?!" "LET ME SEE!!!",I gasped. It felt so GOOD! "Just a sec'..I have to put a little makeup over the band in front. Okay...turn around!" I turned to look in the mirror....Oh God...I don't believe it....I looked over at a smiling Andrea, she nodded her approval as I turned back to look some more.... running my hands through my hair..flipping it like Cindy did off my face, loving the feel of its silkiness on my shoulders and back. "You don't have to brush it at all baby, just shake you head or use your fingers to move it around...it's supposed to look a little tousled and wild. Look, like this..." She stood in front of me and put her hands and fingers into the sides over my ears and pulled it out to make the sides a little fuller, then fluffed the top with her fingers. "See? That's all there is to it" "And look at this...you can pull up the sides or back with clips and it still looks like real hair cause of the band." She pulled both sides up and back and fastened it with gold clips, exposing my ears and making the back even fuller. "Do you like it this way? I think it looks really sexy like that, it goes with a formal dress look". I had to agree. I stood up and twirled in front of the mirror admiring how I looked. "Okay..Okay.. Miss Primadonna! You look fabulous I know...but don't get crazy on me.. all I need is you telling Cindy you want to stay this way and I'll never hear the END of it!", she laughed. I looked at Andrea and said softly, "where is my necklace and earrings and stuff?" She laughed out loud, shaking her head, "Oh boy, we have created a MONSTER haven't we? Cindys mom has them for you."

We were just about to go out the door when we heard Mom yell " Are you two girls almost ready? We're going to be late!" Andrea yelled back, "Here we come!....I don't know if you're ready for this .........look". I walked into the livingroom where mom and Cindy were standing - also dressed in cocktail style dresses. Cindys mouth dropped wide open when she saw me come in, turning slowly to show off my dress and hair. I tossed my hair back imitating her as she opened her mouth to speak...unable to. I turned to Vicky, she was smiling like a cat as she walked up to me. She held one of my hands in hers as she brushed a stray curl off my face. "You are absolutely BEAUTIFUL! baby...STUNNING is a better word!", she whispered, "are you happy with my little scheme?" I nodded yes, my hair brushing my back and shoulders softly, bringing waves of pleasure through me. "Thank you Vicky" I whispered softly. That was all I had to say...she knew what I felt at that minute, "I'll pay you back whenever you're ready" Vicky casually lifted my ruffled skirt and rubbed my dick, which was straining at the tight thong panties. "Later baby,later, if you have any left after Andrea and Cindy are through with you" she said. "Don't worry, I'll always have a nice hot load for your mouth" I whispered.

Vicky just stared into my eyes dreamily and reached out with her hand and caressed my cheek. "Excuse me....hate to break up this mutual admiration society" Cindy interupted, "but we really have to be going! Hurry up and get your dress on Andrea...we'll wait in the car." She turned and walked out the door, gazing again at her mother and I still holding hands. "You look a little bare, I think you need your jewelry" she whispered and took a box from her purse and opened it, "Here..let me...lift your hair,sweetheart". As I slipped one hand through the silky hair..lifting it off my neck.... she fastened a simple gold chain around my neck. I dropped my hair...God it feels wonderful on my back...and lifted the chain to look at the pendant. "to Cathy, love Mom" it said on the back of the heart. I looked at Vicky with a puzzled expression..she quickly said "Cindy called you Cathy, but I think you look more like a Cathy!" I smiled...Cathy....I like it! Vicky smiled with recognition..."let me put your earrings on...it's a bit difficult until you've done it a few times" She screwed on a beautiful pair of gold and rhinestone drop earrings that fell about 2 inches from my lobes, very simple but elegant, and very feminine. Next, she slipped a gold band bracelet on each wrist, and a gold and pearl friendship ring on my ring finger. "This binds us together....no matter what happens between you and Cindy - I'll be here for you. You're making a dream of mine come true as well! Any time you feel the need...come to me and I'll dress you pretty. All this and more will be here if you want it."

Just then Cindy began tapping her horn for us to hurry. Andrea came out of Vickys room wearing a drop-dead kelly green glitter dress that showed all she had....which I mentioned was a lot! "WOW WOW WOW!" I whispered, "are you trying to show me up or what!" Andrea laughed as did Vicky. "Well...I simply can't have everyone there staring at YOU all night can I? Oh..it's Cathy, right.. I forgot to give you this before" , and handed my a very pretty black evening bag to match my dress. "All your makeup..plus a few `extra' goodies are in there, in case you feel like touching up". "Come on girls.. PARTY TIME!" , Andrea giggled, and off we went to........

...........The CLUB!

On the way to the club - which was about an hours drive away...Vicky, Cindy, and Andrea gave me pointers on how to sit without destroying my skirt; how to move; how to hold a drink like a girl; stuff like that. I was pretty nervous still...not that someone would recognize me...no chance of that.. but that I just couldn't be convincing as a girl. Guys and girls just do things and move so DIFFERENTLY! They tried to convince me that we could pull it off, and fussed over my hair and dress the whole way there. Vicky was mesmerized by my wig...running her hands through it like a guy would and stroking my shoulders and arms. She was clearly very turned on by the whole deal. Andrea too was entranced. "I still can't get over it..", she said, "if I didn't KNOW it was you...Damn...you are so beautiful!" I must have been blushing, and Cindy was a little annoyed by the attention... "HEY!..Come on!...he looks good I admit..but he's still a GUY..REMEMBER?"

Andrea shot back immediately.."Oh shut up Cindy!..YOU STARTED THIS..AND NOW WHEN YOU SEE HE LOOKS AS GOOD AS YOU....AND ME!...YOU GET BITCHY! IF HE WAS MY GUY..I'D HAVE HIM IN A DRESS EVERY NIGHT!" I was shocked to hear Andrea come to my defense so vigorously, I never suspected she had any kind of feelings for me at all! Vicky jumped in next.."Andreas right honey", she said softly, "WE did this..it was OUR idea...it's too late to change your mind over putting your man in drag. Just relax and enjoy it." "Okay..Okay, I'm SORRY! I just never planned on it getting out of hand like this! Look at him for Gods sake!....he's GORGEOUS!!" Vicky jumped in again.."That's RIGHT Cin..he IS. I planned this - right Andrea? - you were going to mess around and do a half-ass job!...he'd look like a FOOL! I won't let that happen! I don't know if you realize what he's sacrificing for you...so what if he's having a little fun with this....he's doing it because you ASKED him - no excuse me - DEMANDED he do it! I just closed my eyes and pretended not to hear all this; but I have to admit...hearing Vicky and Andrea blast Cindy like that...for me...I was shaking. Yes..I had fantasies about how I would look dressed like a girl....I think most guys have if they would be honest...but this was clearly in a different league altogether. And the hair business I was really enjoying! Well, it was too late now..if Cindy couldn't handle it too bad....I knew a least two other ladies who could! I couldn't resist it..." Want to cut your hair on me Cindy?..go ahead... I'm sure Mom will wear this wig for me...won't you Mom?" Vicky burst out laughing.." Baby..you KNOW I would...but I'm not sure I'd be able to get it OFF you! And besides....you have to give it back to Andrea tomorrow!" "No" What was that? "What did you say Andrea?" I asked. " I said..NO!. you DON"T have to give it back...DAMMIT!" Cindy looked over at Andrea - who was staring out the window - "Andrea..what the HELL are you trying to SAY!..THAT WIG COST $750 GODDAMN DOLLARS! HOW THE HELL CAN I PAY FOR THAT?!" Andrea calmly looked over at Cindy and said matter-of-factly, "Cindy..... you don't have to pay for it...I already did. Two wigs equals 1 blowjob and 1 fuck a week for that prick I work for. (TWO wigs?)" "But WHY", Mom asked. "For HIM, DAMMIT! for HIM! I HUMILIATED him in front of all his friends... just to be COOL! I hated myself as soon as I saw his eyes but it was too late! When I agreed to help you with this game I thought you were serious about playing the game - but I found out - like your mom did - that your little game would end up humiliating him MORE and possibly ruining him in this damn town! FUCK you, Cindy!...Fuck you! He deserves BETTER than you! He's worth sucking that prick off every week! He can have me any time he wants....any time for anything. I didn't realize until I spent time with him what a great guy he was."

Andrea turned to look back out the window. I could see tears running down her cheeks! Vicky and I turned towards each other, both of stunned by what had just happened. I leaned forward and put my hand on Andreas shaking shoulder and she laid her cheek down onto my hand affectionately...I said softly, brushing her soft hair away from her face.."Andrea.....you don't have to do that for me....I was upset, sure... but it's not worth giving up your self-respect over.....I'll take the wig back tomorrow and tell the bastard the deal's off..and make sure he knows I'm not kidding. This is getting out of hand now, maybe we should call it off, Okay?....Andrea?...Andrea...Okay?" The floodgates opened ...Andrea began sobbing uncontrollably. " SEE WHAT I MEAN CINDY?...DO YOU GET IT NOW? LISTEN TO HIM!..HE'S WORRIED ABOUT MY SELF RESPECT! I..DON'T...HAVE....ANY SELF RESPECT! I'M THE TOWN SLUT REMEMBER! BUT HE CARES!... HE CARES! OH GOD WHY CAN'T I EVER WIND UP WITH A WINNER LIKE THAT!!!" This thing was rapidly going all to shit! I didn't know what to do or say now. "STOP THE DAMN CAR CINDY...LET ME OUT!" Andrea cried. She jumped out of the car almost before it stopped and ran down the block crying. "SHIT!!!" I yelled and jumped out after her, nearly falling on my ass. Forgot the damn heels! I caught up to her quickly and she just collapsed crying in my arms. I held her close, smoothing her hair, trying to calm her. "SHssssssh, Andrea, it's okay.... it's alright....I care about you...we'll always be friends, you can always talk to me." I lifted her chin up and looked into those green eyes....... "Andrea..listen to me honey...I'LL TAKE CARE OF YOUR BOSS" She looked up at me and whispered between sobs, "I know you will baby... that's why I won't let you. I have the goods now - in more ways than one....you just made my mind up for me.....I'm not giving him anything..he's going to give me."

We walked back to the car with our arms around each other waists. Vicky was standing by the door waiting for us. Just before we reached the car, Andrea wiped a tear out of her eye and giving a big smile said "ya know...you REALLY swing your ass real nice when you walk in heels. I gotta get you some 4 inchers and see how you look in them!" Vicky heard the remark and we all laughed together. Cindy just sat behind the wheel and sulked...a hint of what I would see often in later years.

 

to be continued in Part 3.................

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© 1996 by Cathy Evans. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.