A New "Orient"ation, Part 2.... free porn video

A New "Orient"ation..... Part 2 by LaShaunda After my one night of pure fun and "preasure" with Ayumi, things snapped back into my hard, cold, financially-bleak reality very quickly. Soon, I was back at work at Hooters, trying desperately to keep my head above water as a junior manager in that restaurant. Things were actually getting better at Hooters though. The work was getting easier as I learned to do it, and I felt more comfortable there. However, managing at Hooters was NOT I wanted to do for the rest of my life. I would have a heart-attack by age 40 (both from the food and the stress.) However, because of the long hours I was required to work there, now as a junior manager, it would be VERY difficult for me to ever take college classes, or get any kind of training to help me change occupations. I was quite despondent at the moment. I still thought of nothing substantial for the next week or so except my one night of fun. I wrote "Ayumi Horuchi" on Facebook, telling her what a fun time I had had last weekend, and that I couldn't wait to return for our next "session." She was equally eager to see my message, and to return the compliment. She was practically gushing when I wrote her, saying that she "couldn't wait to have me as an honored client again, xoxoxo:-)." I felt rather flattered just to have someone notice me and drop me a line on facebook (especially a very sexually-charged woman like Ayumi.) The one thing that surprised me, however, was that incredibly, Ayumi was the mother of two younger teenaged daughters (as listed on Facebook), who were both close to my son's age. I was shocked by this, because when I first met Ayumi, I had taken her to be about 22 or 23 years old, and possibly even younger. However, to me, I'm sure all Asians looked relatively younger for their age, at least compared to Caucasians. Also, Ayumi's age was probaby hidden somewhat by her makeup and the dim lights of the salon. She may have appeared older to me if I had viewed her in plain daylight .... However, it amazed me that Ayumi was still probably right around my age. Since she was about 32 years old, she had aged damn-well, which was especially impressive for a lady stuck working in that kind of environment. Another thing I noticed, however, was the amorous new "passion" Ayumi had seemed to show for our "massage session" once I had blurted out that I had a fetish for crossdressing. When we started the massage, I had basically been a regular John for whom Ayumi had just wanted a routinely quick yank-and-pull, and then I'd be hustled out of there. However, it had seemed that my confessing to want to wear tights and dresses had "flipped a switch" on the session, and she eagerly began to try and get me to open up psychologically, and with more details (asking me if I'd like to be an Asian or a black woman, stuff like that.) It seemed that once the topic had turned to crossdressing, she had gotten much more energetic about the sex-job, and perhaps I had struck a nerve with her somewhere. She was not only eager and enthusiastic about pleasing me and having me back as a repeat customer, but she showed her "Saki" off to all of her co-workers too... Now that the moment had passed, I thought little about the blur of what had actually transpired in that massage parlor, but I was quite floored that Ayumi had shown so much Interest in me. I was absolutely flattered that she even wrote me back and added me as a friend on Facebook. I tinged with delight as I read her message again and again, perhaps even dreaming that one day I could grow the balls (lol) to ask her out for a real date!!! The only problem was, however, that she was also apparently a single mom supporting two teenaged daughters, and it would be financially problematic enough for me to have to take on any more kids. I could not even manage the one I had (Brett). I also did not really know anything in detail about her "life situation," or if the truly had any interest in me besides just a flirt to get me back for a quick massage + a tug-and-pull. However, I was looking forward to another "escape" with Ayumi this Saturday, so I wrote her back on Facebook, "YES, "Saki" will definitely be up there on Saturday... U working?" "Oh yes, Ayumi work all-nighter Saturday. Will Saki come wearing dresses?" "Uh, Saki has no dresses yet," I said, "No shopping money." I felt a bit awkward typing that, but it was amazing just to be doing some internet role play with this Asian sex-worker babe!!! "Oh, no problem, Saki come in pants, but you can change into something sexy here..." (Something sexy here?? What the heck was going on? What was I being set up for? I also hadn't worn a stitch of female clothing since I was 17, and I had pulled on my sister's tights for the last time..... I had no idea where this was going, but I was tremendously peaked. Was she going to lay out female clothes for me to wear? (OMG, I was role- texting as a make-believe Asian woman now!!)) "Saki see you soon, Saturday at 8 PM." "YAY, I can't wait (smiley face)"... (Ayumi) So I was now tremendously excited about my "date," which was really more like a "massage appointment." I guess I kind of figured that maybe I'd have weekly Saturday "appointments" with Ayumi, which would definitely relieve the stress I was currently under. However, I really could not even afford to pay 90$ a week or so to go and get one orgasm, however fun it was. I liked the idea of being one of Ayumi's "regulars" though, as she was so incredibly attentive and willing to cater to my unique fetishes. It was a once-in-a-lifetime thing to find a stripper/sex-worker to do this for me. I logged off facebook, and I decided that I, too, really wanted to have a memorable experience next time with Ayumi. I did not know exactly what she had planned. However, I decided that I would try and make myself a bit more "presentable" for her for next time. I went into my restroom and spent an hour shaving off my scraggly chest-hair. Then I completely shaved my arms, my legs, and even my butt (!!) totally hairless and smooth. I figured that maybe Ayumi would like this a lot, especially if she was expecting me to role-play as "Saki." Then, I decided that I was a bit embarassed by my puny physique, so I decided I'd chisel up a little bit..... I did 5 sets of sit-ups, and then I jogged around the block for half-an-hour. I felt quite refreshed and ready to take on the world again. --- It was back to the cold, blistering reality of my life as I started my next long and hectic day. I had blown through much of my scant "pocket money" at the Oriental salon last week, and now I was a week away from my next check from Hooters. Even working full-time there wouldn't cover what I had to pay for rent and child-support for Brett. I wasn't covering enough. There was only one thing I could think of.... I turned up unannounced at my older sister Rachael's house, where she lived with her husband, Nick, and her son, Michael. I actually had only seen my sister about 3 times in the last 14 years, as I was off in the Army. We really were not that close. Growing up, I think she knew that I would secretly dart into her room and wear her clothes and her pantyhose, which is one reason why she kind of grew "weird" to me by the time I was a teenager. I know there were a couple times when I accidently ripped her pantyhose with my toenails, and I had no way to hide the accident. I would just discreety stuff the tights back in her underwear drawer, but I knew, that she knew what I had been doing in there... (groan).... I would never see her wear those shredded tights again. However, I don't think that that was the real reason we didn't have a relationship. Rachael was always a beauty growing up... She was two years older than me, and a real go-getter in every sense of the word. She was a complete "Prep" and active in things like cheerleading, student-council, and the Pep-Club..... I was a loner and a slacker, with few friends. We had nothing in common really. Rachael was a Valedictorian.... she went off to college, graduated, and married an insanely-successful guy who was a financial advisor. As far as I recalled her telling me, Rachael got a job managing some big corporate office downtown. From pulling up to their big suburban house, it was obvious that both Rachael and her husband Nick were rolling in the dough. They were the epitome of "Keeping up with the Joneses." "Please," I asked my sister, "Its just a loan to cover expenses, until I get back on my feet. I have a job too." "So what," she said, "You're just going to spend the money on groceries, and then owe me 10,000 dollars? And you are up to your neck in child- support payments. You're just digging your hole deeper, and trying to drag me with you." "Please, I am your brother," I begged her, "You have to do something for me." "I'll think about it," she said, "But you gotta show me something. I mean, I'm not just going to loan you spending money. Now, if you were using it to maybe start your own business or something like that, where you would get a return....." (She was such a fucking shark.... why did I even bother. She also had more money than she knew what do to with, which was the ridiculous thing. Last year, for example, her and her husband bought season tickets to the Metropolitan ballet, even though they both have no interest in ballet. It was just a "Prestige" thing for them to have box-seats next to their friends.) (She could have given me 1,000$ cash and barely batted an eye. That was just one-month's utilities for them.) "Look," said my sister, "Here's what I'll do.... Brett will be 18 in almost four years, so I'll cover you with a loan unti then. Then when he's 18, you'll no longer owe child-support, and you can start paying me back. If I give you over 100,000 dollars, the government won't tax it either, as its a one-time-only gift between family members." "100,000 dollars...." (My eyes lit up). "This will give you all the options to get you back on your feet. You can use the money to invest or start some venture that can start paying exponential dividends. And after your son is graduated, you can pay me back at your leisure." "Oh thank you, thank you," I said, "You are a godsend." I then scampered out of there.... ------- So I finally had a degree of freedom, and some disposable income that I could throw around, once the massive bank-transfer and paperwork went through. Paying Rachael back would be a problem down the road, but she was family. I was finally able to go out and buy some new clothes, get my car painted and an oil-change, and have a few nice dinners. I was spending quite a bit of money, but that 100,000$ in my account seemed rather... limitless. Anyway, before I knew it, Friday night was soon here, and I had every intention of getting down to the parlor and "wooing" Ayumi. Now that I was financially free, I had a bit more confidence about possibly ASKING HER OUT... I knew that she was single, and as she was a single mother, I had a strong feeling that maybe she DID have an interest in me. Maybe she WAS even looking at me as a possible partner for marriage, to help her and her undocumented kids stay here by marrying an American citizen? Was this a possibility? Ayumi had shown a real interest in me, even to the point of Facebooking me. The more I thought about it, the more the idea of Ayumi intrigued me. I LOVED the idea of her possibly being a romantic partner, and I could rescue her from that foul den!!! So with all the thoughts of my new "crush" raging in my head, I went into the bathroom and caked deodorant on my hairless armpits. I spritzed myself with a very masculine cologne, and I wore a nice shirt and slacks. I really wanted to be the "Man" for Ayumi. I had failed with women of the "American Culture," who all expected me to be have to social norms and tip-toe around an excruciating courtship ritual. However, with Ayumi, I had found a girl who could just let me "be myself," and she had no preconceived expectations for how I should act, as she had limited experience with dating American men. In the salon, she told me I was one of her favorite customers of all-time. In fact, I probably did compare VERY favorably in her expectations to some of the jerks she probably had to deal with on a regular basis. I was getting more and more optimistic about my actual "chances" with her, based on all my reasoning. So with hat in hand, I sped back to the salon, rather eager for a totally sensual experience with Ayumi. I checked my look in the mirror one more time, and I was every inch the All-American man. For the first time in years, I felt very confident. I was not even nervous as I rang the doorbell of the salon. A girl came to the door. Nabiki answered. She was wearing a white basque-leotard and white tights, with lacey white panties underneath. She was so tall, striking, and beautiful, and I rather thought that she would be my "plan B" for a session if Ayumi did not totally have my heart. "Oh hi Saki," she giggled.... (Suddenly, my careful facade of manhood took a massive blow by instantly being referred to as "Saki.") "Please, call me Ryan, Nabiki," I begged, "Can I have Ayumi tonight?" "Ohhh yes, no problem Ryan," said Nabiki, "Just let me go get Ayumi. She is free of customers now." "Thanks so much." I sat and waited anxiously in the lounge, for what seemed like hours. Tina, and two other Asian girls I had yet to meet were also just hanging out there with me, possibly waiting for clients. "You sure you no want to come with me," said one of the other girls as she took my hand, trying to hustle me, "I love you LONG time... Me make you verrrry hard. Me so horny, me so horny!!!" Even though she was attractive, I had to reply, "No thanks, I already have a date with Ayumi tonight." She let out a kittenish mewl of disappointment. I felt rather bad for her, as God knew how difficult it really was to get good customers here, or ones who tipped well. Then, Ayumi emerged from one of the back rooms. She was wearing a green-nightie with thicker black tights..... "Ah, Saki, Saki.... So glad you make it... " I was so glad to see her bubbly and smiling face. She turned to the solicitous Asian girl and said, "Saki here one of my bessst honored clients.... He is one of the ones who dreames he is girl." The other Asian girl now chuckled, "Maybe next time, Saki," she laughed. I practically cringed of embarassement. "Can you please call me Ryan," I pleaded with her. "I still like being a guy." "Oh, ok Ryan, I sorry, it no happen again. I just want to make sure that Yoko know what you like, in case she give you massage one day." She took my hand. "Honestly Ayumi," I said, "I really think I only want to get massaged by you when I come here, if you know what I mean. I'm not interested in the other girls." "Ohh really," said Ayumi, her interest peaking. "I just really like you, that's all," I said.... (Should I make my pitch to her now? It seemed my charms were working, and I was getting her interested. I could ask her out, if I wasn't such a pussy... (no, a wimp!!!)) "Of course Ryan like Ayumi," she said, "Lots of men ROVE Ayumi. I very popurar girl here, because I risten to what honored clients want." "Oh, I see," I said. I think Ayumi really just was interested in me from a business standpoint, and catering to my fetish. "I'm sorry," I said, "But I think I only really want to see you, since you are the most attractive girl who works here, and you totally understand me." (I decided to drop the idea of asking her out for right now, as I figured I should get to know her better and not "blow it" by coming out with a proposition too early.) "That so nice of you to say," said Ayumi, "And I had much fun with you last time. Anyway, do you need shower before we start?" "No," I said, "I showered before I came." "You smell very nice," she said, whiffing my cologne. "Thanks!!" I quickly paid her 40 for the hour, and another 50 for the hand-job + a tip to come. I decided not to go for the BJ yet, as I wasn't sure that I would be able to acheive an orgasm with oral sex, and I didn't want to blow extra money. Ayumi led me by the hand into a massage room, "Now, we alone, so I go back to call you 'Saki'. I told you I had VERRRY special surprise for Saki. I remember you even say that you dream of being one of the Asian girls working here??? One of our sisters?" (I might have said something like that, but I don't recall saying those exact words. I was a bit nervous about where she was going with this.) "Just relax," said Ayumi, "We ALL sisters here, and we in verry much privacy. It now time to buird on what we do rast time, and have more fun with Saki. Tonight all about you and your secret dreams." I was quite nervous now as she reached over into a chest of drawers in this room (we were in a new room that had a couple dressers and a double-sized bed). I was both nervous and and apprehensive as she pulled some colorful garments out.... She turned around and held the clothes in front of me.... "Surprise!!!" She eagerly showed me a lavendar nightie, large black heels, a pair of black pantyhose, and a pair of black panties. I was quite shocked to see the clothes, and also rather excited, as I had not actually crossdressed for so long. I would now get to do it for an hour, role- playing as "Saki." Based on her Facebook messages, I wondered before I came here if Ayumi would want me to actually crossdress with her, instead of just roleplay? Crossdressing would be "the next level" for me and keep me engaged as her client with regular massages that got progressively more intense..... "You want to do or no," said Ayumi, giving me the choice? "I understand if you no want to dress pretty for me and no be Asian massage girl. Instead, if you want to stay as boy, we just do long massage and then try again for regular handjob." Looking at the tights, however, my deepest desire was to get inside of them!!! Also, I knew that deep down, just a hand-job from Ayumi would end in a dismal failure..... I was here, NOW, and I had the ultimate chance to dress up in the way I hadn't dressed in years, and live out my wildest fantasy. Also, Ayumi would ROVE me if I kept playing along with her. She had also gone through all this trouble to set it up so I could dress as an Asian Massage girl, after my revelations in our last session. I quivered. I sensed that my decision (to dress or not to dress) would be a watershed of sorts. Ayumi held up the tights and nightie expectantly. She WANTED Me to dress up as her cute co-worker. I had come in here as a totally straight man, ready to ask out the girl I had a total crush on, and now I was seriously considering donning panties and tights!!! "What the hell," I thought, "I only live once. And if this leads to an even more earth-shattering orgasm than last time (which I know it will), then it is worth it. Also, I am still a man, except for what goes on in these rooms." I took the tights and panties from her tiny hand. I dropped my dress- trousers, revealing my smooth, hairless, and skinny legs. She giggled. I took my shoes off, and next my shirt. Soon, I was totally naked, just standing before her. She put her tiny hand on my shoulder. "Ohhh, you need help dressing," she asked? "You need help purr on tights??" "Maybe," I said as I put one foot into the hole of the panties, "Its just been so long since Saki dressed....." "We fix that real quick," she said as she pulled the black full-butt panties up my leg. She got the panties up and once again covered my genitalia with my new undergarments. She "grazed" my male member once again as she adjusted my panties to fit properly. "Oh my," I thought... "Next, tights...." I took the pantyhose and tripped one foot into each ankle-roll. I felt so silly as I got the tights up to my knees. It was the first time, however, in over a decade I had donned pantyhose, and I had almost forgotten how good and cold the garment felt. I did not feel that awkward pulling the pantyhose on, and Ayumi helped me tug out the wrinkes as I tugged them up my legs. As I got the tights up over my knees and hips, I began to realize how great it felt to be able to be able to dress in a SECURE environment like this. Before, I had never really been able to enjoy dressing in my youth, as I was always so fearful that someone would burst in on me and catch me in the act. This was so much more relaxing and pressure-free now. I got my black pantyhose up over my big male bulge in my panties, and then up over my waist. I got the waistband straightened out around my tummy. I went back over my legs, and pulled the hosiery up nice and snug. Finally, I straightened the pantyhose seam and gusset directly centered over my crotch. (Yes, I was FULLY wearing tights, and I was completely pantyhosed now.) Without hardly realizing it, I had now sprouted a massive boner inside my panties and pantyhose. "See," said Ayumi, "It my job to learn and cater to all desires of my honored clients. You my honored client now, and I learn what you like so I satisfy and love you long time when you return." As for me, it had been years since i had felt the sung coldness of tights on my skinny legs. I looked down, and I actually was shocked at how "girlish" I looked (and felt) from just the waist down. "Ok, now your nightie, so you wear our uniform and be one of us," chirped Ayumi... 'You well on you way to be Asia girl!!" I stepped gingerly into the lacey and lavendar nightie, and I realized that it was the same cut as the one that Ayumi had worn during our last "session." I pulled it up over my legs and torso, and I delicately put both of my arms through the spaghetti straps. I felt so silly getting it on, but the nylon and chiffron material rubbed so amazingly against my tighted crotch. These were new sensations I had yet to feel in my entire life, as my sister had not owned such garments. I caught a glimpse of myself in the mirror, and even though my face was male, from the neck down, I was smooth slender and hairless, and wearing ladies' lingerie. From the neck down, you would have definitely assumed I was a woman, except for the fact that I had no boobs or clevage (yet). Even then, I could have easily passed for a flat-chested female. (I was entering totally unprecedented territory for me, and my hitherto- mild crossdressing fetish). "Ok, now heels," said Ayumi, as she produced two shiny black 4-inch spikes, similar to the ones that she herself wore. I sat down on the bed, and I inserted my nylon foot into the spiked mary-janes. It was a strange but pleasurable sensation to see my black- pantyhosed feet inserted into feminine footwear, which created the illusion of having entirely female legs (like that of a showgirl!!). I buckled the straps across each heel. The shoes were very tight, but made my feet feel very "secure." (What would my son say if he saw me now???.... Yikes!!) "Ohh yay," clapped Ayumi as I got the shoes on. I stood up and studied myself in the mirror now. I still felt a bit wobbly in the heels, and I took short and gingerly steps. The heels also made me "pose" differently and clearly brought out my calves and the feminine contours in my legs, as well as pushing my butt up into a nice plump derriere!!! I closely examined my reflection up and down, not sure what to make of myself. However, after a minute or so, I cracked a smile, and I even did a twirl. "Yay, you one of us now Saki, see....." beamed Ayumi. "I'm... not... sure, how I feel," I croaked. I was excited, but I had mixed feelings about all of this too.... "Wait," said Ayumi, "I have one more thing for Saki to make her feel like complete woman. With that being said, she went back to her chest of drawers and procured a long-dark jet-black hairpiece.... "You wear this," said Ayumi as she crowned my close-cut male head with the wig. I was not expecting this development at all!!! "See, you feel more like Saki now..." I looked back, and except for my male face peeking out from under the hair in the mirror, I would have been completely a woman, especially from the rear view. "Ohh, you Geisha Girl now," chirped Ayumi, "I make Saki complete preasure woman, who show happy-time to honored clients!!! This your fantasy, no?" "Oh Ayumi," I said, "Yes, I have always dreamed of dressing this way, but just in private. I kind of have mixed feelings about it all though. I don't mind doing it, but just as long as it stays private." "No problem rover," she said to me, "This is all your fantasy. She next came and rubbed her petite body up against my torso and abdomen, more than amply grazing my crotch. My penis was situated in an erection that sited itself directly in the front of my panties and and pointed upward. Every movement I made or Ayumi made sent the ripples of nylon material stimulating the sensitive underside of my male organ. I was getting hard as Ayumi was pressing her own body closer and closer against my crotch. She could see what effect this "foreplay" was having on me. "So, how you like being Saki," she asked me??? "I love it, I love it," I moaned in ecstasy. It was true, I loved these new feelings I had, and the fact that Ayumi was targeting my enraged manhood in no uncertain terms wasn't helping. The more she "got me going," the more I got into the way I was dressed and pretending to be a woman in role-play... I continued, "I absolutely love how you dressed me. I don't mind being Saki at all, the pretty Asian pleasure girl... I such a little plaything," I bemused. I broke off from her embrace, and I twirled around again in front of the mirror, driving the spike of my heel into the carpet. "Oh, I so glad," said Ayumi, "I so glad I make Saki's dreams of becoming Asia-girl cum true..." Ayumi came over to me again, as I was admiring myself in the mirror, "Now, Ayumi help make Saki even more comprete..." Ayumi took one dainty hand, and reached up under the skirt of my nightie. She grabbed my bulging crotch and began to grab, rub, and squeeze it through my tights and panties. She was a total expert at manipulation, and my cock quickly swelled up to epic proportions and stuck itself to my belly. I stood there and just moaned with pleasure as Ayumi worked on me... "Wait, wait," said Ayumi, "I have even better idea... Lets go show "the new you," to the other Happy-ending girls working here... Maybe they want to see Saki too?" " I think Nabiki especially VERRY much want to see Saki," she purred. (Was she proposing I go out in my new attire and twirl for all of her friends? No, WAY too embarassing!!!) "Uh, I don't know," I said... "Oh, come on Saki, it be fun." "I thought this was just private...." "Ohh," she pouted, " I just thought it be a bit of fun to go show you off, and I think you may like it too." "I don't want them all to laugh at me," I said. "I'm just too nervous now." (I had just walked in here 30 minutes ago as a "complete man," and now Ayumi wanted me to go prance around with a bunch of her fellow Asian nymphettes, and have me pretend to be one too!!!) "Ok, maybe next time," pouted Ayumi, obviously leaving the door open for a future "meet-and-greet!!". Ayumi went back to work on me, rubbing me harder and harder... "Come to bed," she instructed, "And you lie down and let me finish you." I relaxed supinely on the bed again, and this time, Ayumi stuck her hand down my tights and panties, grabbing my cock and rubbing it against all of the nylon material I was wearing. This was now BY FAR the most pleasurable sexual experience I had ever had, bar none. Ayumi was such an expert at all of this, and the fact that I was dressed in tights and ladies' clothes brought the experience completely into my dimension. My deepest, darkest fantasies WERE to be a woman (but not necessarily the Asian variant), and Ayumi was completely playing to that. It also helped that Ayumi herself was so bubbly, effervescent, and personable. She was exactly the type of fun and flirtatious masseuse or "comfort girl," I would have most liked to spend time with. Ayumi was really getting me going as she stroked me off. She next looked into my eyes, and I looked longingly back up at her. It was becoming clear that maybe we did have more of a special bond beyond that of "masseuse and client." I was really starting to like her, and she seemed to respond perfectly to my fetishes and desires. It seemed to go beyond simple catering, to the level of her really sharing an experience with me. (It felt amazing having a strange hand on my penis, with absolutely no idea the directon of the next stroke to come, or what she was planning to do with me. The pleasure was much heightened by having someone else stroke me off, instead of just the (predictable) me doing it to myself.) "Ok Saki," she said, breaking me from my reverie..... "Now I get you to finish off." That being said, Ayumi swung onto the bed, and mounted me as she still grappled with my joystick. She climbed into bed with me, siting herself directly over my hips and abdomen. Ayumi finally let go of my engorged cock, and sited it back nicely inside my tights and panties.... "Ok, now I grind on you like you are real lady," said Ayumi... "I know you no need handjob, but you need to be "preasured"...." (What was coming next!!!)... (Ayumi was totally taking me for a ride, literally and figuratively.) Ayumi then began to press her legs and her own tighted crotch direcly against mine, bumping hard against my dick and totally getting me going. She started to generate lots of friction, grinding on me and laying down on top of me. My tights and panties rubbed together with her tights and panties....My legs rubbed together with her legs. I was the hardest I had ever been in my life!!! Ayumi was now totally grinding on me in the missionary position, almost as if she had the dick, and I had the pussy. The front of her tights was making the most amazing rustling sound as it jostled with the front and gusset of my tights.... The POUNDING on me was so hard, and moving at a fast and furious pace now. "Ayumi," I gasped, "I may explode in your tights and panties, is that ok..." "Sure rover," she said, "This all your pleasure." She grinded on me so hard, and I felt only seconds away from crowning and coming. "Come on baby, Come on baby," she counseled as she directly grinded on my underside, "Cum for me, cum for me!!!" I could stand it no more, and I erupted like a volcano inside the tights and panties that Ayumi had provided for me. It was the most intense eruption I had ever had, complete with 9 or 10 glorious spurts into the nylon. "Oh, that good, that good, I even feel that hit me," said Ayumi..... I finally finished squirting with pleasure, and then I crumpled up on the bed, just laying there in sheer exasperation for a minute or so. Ayumi lay on top of me. She looked into my eyes and lovingly stroked my face. I stared back longingly into her beautiful yellow face and slanty eyes. "That all ok," she said, "I want you to do that with me, every time." "I'm sorry I made a mess," I stammered, now leaving the role-play and coming back to my "Ryan" persona... It was true. I hadn't squirted so far as to barely stain my nightie, and I had TOTALLY creamed the tights and panties. It was the biggest, sloppiest puddle I had ever seen. "Oh wow, I impressed," said Ayumi, surveying the damage.... "You have big explosion, bigger than most men..." I did not know what to say, but now, I was a bit wanting to get the soiled and dripping-wet clothes off... "It ok, it ok," said Ayumi as she quickly unbuckled my heels and pulled off my cum-stained tights and panties. She took the hosiery and put them in the hamper. I quickly took my nightie off too. Ayumi then took a hot wet-wipe and expertly cleaned off my crotch. "You my FAVORITE client," she reassured me. Something in her tone of voice made me think that she was rather sincere about me being her favorite, as opposed to this being something she just said to everyone. "Ok, you get dressed now," she said. I took off my wig and got my guy clothes back on quickly. I reached into my wallet again and gave her another 20$ tip. "That was so amazing Ayumi," I said... "Oh, you come back and see me as much as you want... Next time, we have even more fun. Next time, maybe we try blowjob, but you cum easier if you also pray dress-up." "Ok," I said, not without some nervousness regarding the escalating nature of my sessions with Ayumi. However, it was undeniable that I had just had the biggest orgasm of my life, even if it was with me wearing tights and panties and her calling me "Saki." Even though I had a deep and dark crossdressing fetish, it made me nervous to come here so casually and not "get-off" in the "normal ways," of most guys.... "I have one gift for you before you go," said Ayumi, "This is for you, as my most honored client. I want you to take these home with you, so you think of me. Ayumi reached to the floor and picked up the black heels, and the nightie I wore. She next reached into the dresser, and she pulled out another fresh pair of black pantyhose, and a new pair of black panties. She handed the new pile clothes to me. I took then gingerly, not sure what exactly to do with them. "These crothes are gifts to Saki, "on the house" from the Salon," said Ayumi, "You can take these home and wear, or bring back to play more dress up. Or, you buy you own dresses and bring them in." "Uh, thanks," I said, "But I'm not sure how much I'll wear these at home. I probably won't "buy dresses" either..." "Oh, they gift to you anyway," said Ayumi, "You wear them if you want, or not. But now you have you own uniform so you pretend to be massage girl too. And I like having you as one of us." "Well, thanks," I said. I accepted the gift as she put the nightie, tights, panties, and heels into a paper bag. Truth be told, I had every intention of wearing this outfit in my own privacy (at home), but I did not want to admit that to Ayumi. I was totally dressed as a guy again, and (much to my relief), I would not be leaving dressed as a chick. I felt silly carrying ladies' clothes out with me though. "I hope this session be everything you want it to be..." she said. "Oh yes, and thanks again for the outfit," I said to Ayumi as she showed me the door, "I will definitely be back, probably next week or so." It was a watershed of sorts for me, anyway, as now I had my own "very small" stash of ladies' clothes that I would always have at home, to wear whenever I felt like it!! ---- Having an unexpected crossdress session with Ayumi fulfilled my final dreams of wearing tights and heels. In my youth, and in the Army, I had been deprived of any outlet to explore my fantasies.... Ayumi was a godsend. With her, I could finally get my tights on and have a secure venue in which I could live out any desire I wanted. Putting on tights, panties, heels, and the nightie was even more than what I imagined it would be, to be honest with you. The feeling of wearing tights was just sensational. It also felt so comfortable and NATURAL just to be dressed up. After my 2nd session with Ayumi, I was sort of "sated" and relieved for a few days, but I soon began to dream about next weekend, when I would go back and see her again. I wondered what new surprise she may devise for me next time?... (After all, it was her role, as a Geisha Girl, to keep devising new sensations and stimuli to keep her "honored clients" entertained.) At work at Hooters, I still kept dreaming more and more in my moments of "down time," about how the next session with Ayumi would go. She was all I thought about whenever I had a spare second. At Hooters, I found myself increasingly eyeing the 3 really attractive Asian girl waitresses who worked there. I studied their understated curves, and their slender but pantyhosed legs. I was totally captivated by their chirpy demeanors... and I even found myself dreaming, most idly, what it would even be like to BE one of them... (I imagined myself as Saki, a pretty Asian Hooters girl, cheerfully serving tables and letting all of the guys check out her tiny butt in her small and tight orange shorts. I could flirt casually with business men and make massive tips (instead of my paltry manager's salary).... However, such a dream was only a hopeless dream, and nothing more, as my "package" would be visible in the tight orange Hooters shorts, to say the least!!....) - Tanisha snapped me back to reality as I found myself dreaming once again of being Saki the Hooters girl... "Wings ready fo' table 4," she ordered in her strong ghetto-girl intonation. I gathered myself and went and grabbed the trays of hot-wings... My busy schedule not withstaning, I still kept thinking non-stop about my next session with Ayumi. I thought exactly about the things I would say to her, and the sweet-nothings I might whisper in her ear (I still had dreams that she may well see me as the "All-American man" and as potential husband material to enable her to become a citizen??.... (Perhaps her dressing me as a woman was a 'trial' for me of sorts, to see if I was brave and fit enough for her??)) Another inescapable thought for me was the fact that I had had the two hottest orgasms of my life when I had been dolled up, or when I was thinking about being dolled up as an Asian lady. It had always been the case with me that I had only been able to acheive a final climax to my masturbation if I was thinking about crossdressing as a lady. For years, I had deluded myself that I was just like any other straight guy, wanting to "nail and bail," and nothing else, But truth be told, I never thought about purely heterosexual thoughts; and if I did, I always came back to my secret transgender dreams. That being said, over the week, I began to plot out more and more how I would bring the "maximum fun" to my next session with Ayumi. Ayumi had mentioned something to me about "wearing a dress" next time, so by Thursday, I resolved to surprise her and turn up with a dress to change into in the massage-room. We could spend our next session, with her teasing me while I was in a dress, and I would totally explode again as a "more complete" Saki, wearing a full-female "everyday" ensemble. However, it was easier said-than-done to actually ACQUIRE a dress. I fretted about where I could even get a dress on short-notice without getting all sorts of weird looks. I was not so worried about Brett catching me wearing a dress at this point, either. I had custody of him for the week, but he was so busy with school and football practice, so he was gone for 14 hours a day... So I pretty much had the whole house to myself. In the mornings before work, I was able to change into the lingerie-getup that Ayumi had provided me, and lounge or prance around the bedroom pretending to be "Saki." (It still felt a bit weird, but I was just living out my fetish like any normal man does in private.) I also now had plenty of time to get geared up to go out and somehow acquire a (very pretty) dress to wear in for Ayumi on Saturday. ---- On my way to and from work at Hooters, I kept driving by a mid-sized ladies' clothing store called "Dress for Success...." It was located in the back of a strip-mall, and from my casual glances, it seemed to have a good range of dresses and casual/business attire. What attracted me to it was that the establishment wasn't really a "chain store," and it seemed to be tucked away and not frequented by lots of clientle. The store was about the size of a T-J Max or the Dress Barn. I had been scouting it out this week as the potential store where I could buy a dress, and where and possibly enter the store as the only customer. It would be much easier for me to look for a dress and buy one from the cashier if the store was relatively quiet, as opposed to if I was trying to procure ladies clothes in a crowded store filled with (disapproving) middle-aged women. Trying to plan out my visit (so I could shop at the most discreet time possible,) I pulled up to "The Dress Barn" at 10 AM, just as the store opened.... Sure enough, I was the only customer, and there seemed to be only one cashier; an attractive young brunette girl, possibly college- aged. I entered the store nervously and looked around. The store did not have one piece of masculine apparel. I sort of glanced around, trying desperately to think of a non-gay reason why I might be in here or looking for a dress.... She saw me tittering and looking unconfident and anxious..... "Hi, I'm Melissa," she said to me sweetly, "Is there anything I can help you with?" "Uh, no," I said, "I'm just looking..." There was no sign of shock on her face at all, but she just said, "Ok, just let me know if you need anything." She did not seem bothered that I was a guy in a dress shop at all, and "looking" at stuff. (The store was filled with mostly dresses of all cuts, sizes, and colors, and nothing else... I barely knew to begin, but I felt tentative looking at the racks and racks. I was sure that Melissa would think I was so creepy as I began to scout out dresses.) I walked to the back of the store and started looking at one rack of these patterened short-dresses that had polka-dot prints. The dresses felt really soft, and I quite liked the feel of these. They were also only about 10$ each (very affordable). I also noticed a display of tights and pantyhose in the store, a wall of heels/shoes, and other stands of makeup and accessories. Everything in this store was marketed at females... A guy would NEVER be in this store, except tagging-along with his wife or girlfriend. Melissa kept looking over and seeing me nervously checking out the dresses. I was her only customer on a quiet Thursday morning. I prayed that I could maybe get out of here before another lady-shopper came in and was freaked out by a guy fingering around the dresses.... I figured I'd just get something and pay for it quickly, and then high-tail it out of there before the cops were called to bust this pervert!!! (a.k.a me) Melissa then walked over and said, "Would you like to know about our sales? I see you like these dresses by the way... These are some of my favorites, and I think they are so cute and flirty..." "Uh, sales, what," I asked? "Yeah," she said, "If you buy 3 dresses, you get a 4th for free...." "Oh, uh, I think I just want one." ( I could not feel my legs, or my tongue as I spoke to her). "Oh," she said, "I see, you are shopping for a girlfriend?" "Uh, well, no," I said, "Its kind of embarassing, but its for, uh, me." "Oh, I see," said Melissa, suddenly understanding, "I understand now." "I'm sorry," I said, "I should have said sooner. The dress will be for me to wear." (A massive weight now came off my chest.) "That is absolutely fine," Melissa said tenderly, "Just let me know if you have any questions, and if you want to try anything on, that is fine too. Our dressing rooms are in the back. Just let me know." "Try it on!!??" "You actually aren't the first guy to come in here and want to wear a dress," said Melissa. "I've had two others just like you before, and I work on commission. So just let me know if you need anything." (My heart was racing now. I suddenly felt comfortable, and this shopping trip was evolving much better than I expected!!! It also helped that Melissa seemed really cute and accommodating....) "Uh, ok," I said, "I think I'll just look, but I'm not sure if I'll try anything on... I think I'll take two of these polka-dot ones, and two of the flowery ones..." "Good choices," she said, " The Size 7s look like good fits for you right now..... But you really need to try them on though first before you buy. The male body is shaped differently, so you can't just assume that "one size fits all," like it does with some women." "Oh, I'm not sure if I want to try on," I said. "Its ok," she said, "Go do it so you don't have to waste a trip making a return or an exchange... No one will bother you either while you change." Well, I had worn the lingerie Ayumi had given me a few times now, so I was less uncomfortable about dressing in ladies' clothes when I was with other women. Also, something in Melissa's demeanor really put me at ease. I went back to the changing stall and pulled across the curtain. Only my feet were visible to the rest of the store from underneath the curtain, so any new customers in the store would have only assumed a lady was changing back in the room. I pulled off my guy clothes and got totally nude. I grabbed the first dress (a black one with white polka-dots) and gingerly stepped into it, pulling it up my body and sticking my arms through the short sleeves... I looked at my reflection in the mirror, thinking how great my slender and hairless body actually LOOKED in the dress. The size 7 was a great fit. I actually liked what I saw from my reflection, even though I had a male face and no boobs....(I did not really feel just like a "guy in a dress". I thought that the dress was very form-fitting and flattering for me, and showed off my toned figure. I was absolutely going to buy this one and wear it in for Ayumi (with the black pantyhose and heels.) As I spent a bit of time admiring myself, I heard Melissa call from behind the curtain, "Are you doing ok in there," she asked me? "Uh, yeah," I said, just fine. "Ok, let me know if you need help," she said to me. "Do you want me to take a look at you," asked Melissa, "to make sure it is cut ok around the bust?" "Uh, no," I protested. "Well, only if it is ok." "Come on out," she said, "There is no one else here." I sheepishly came out of the dressing room and posed for this cute girl. I mostly still had a "masculine" complex that did not want me shown off to Melissa while I was wearing a dress... "Ohh, that is super cute," she cooed, "And I think you should definitely get this one. It has plenty of room left in your bust too, for when you get your boobs!!" (Get my boobs!!... Yikes!! That comment shocked me, but I said nothing. She seemed to really like dolling me up, perhaps with more gusto and enthusiasm than was normal, almost like I was some sort of dress-up doll. She had a really flirty tone of voice with me. As she checked the dress to make sure it fit ok, I almost felt a bit like I was her "project".) "This one fits you so great... Now try on the rest," said Melissa... I had felt it was a very brave step for me to show myself off to Melissa while I was in a cute dress. Then, I quickly tried on the other three dresses, liking the cuts of each one. I resolved to buy all four. I got dressed in my male clothes again, hoping to quickly make my purchases and dash from the store. "Ahh, with three dresses, and the 4th one marked off, that will be $33.50, with tax," said Melissa as she put the dresses in the bag. "I can't thank you enough for how helpful you have been," I said sheepishly, "I couldn't have imagined that a clerk at a dress store would be this helpful for a guy like me." (I had rather enjoyed myself, and Melissa's vivaciousness totally helped.) "I hope you felt the way you wanted to when you wore the dresses," she said understandingly.... "And don't worry, you can come back any time." "I was so nervous coming in here," I confessed, "And I had no idea what anyone would say to me." "You can always come back in just to hang out or chat, if you want," said Melissa, "But also, have you thought about "accessories" for your dresses?" "Accessories," I asked? "Well, yeah," said Melissa, "Are you just going to wear the dresses by themeselves, or are you going to wear them out?" "Well, no," I said, "I don't think I'll wear them out...." "Would you be interested in looking at our selections of pantyhose, slips, bras,and lingerie, as you will definitely need undergarments with all of these...." (I hadn't thought of this just yet, at least not a bra!!!... Come to think of it though, Melissa was a GODSEND, as a bra would really add another element to my feminine costume that I had yet to consider.) "If you have time, I guess I could check it out," I said.... "I don't even own any bras. To be honest with you, I am buying the dresses because my girfriend is really into role-play. I feel SO embarassed to be telling you this, to be honest with you." "Its ok," said Melissa, "Like I said, some other guys have bought dresses here from me. It wasn't a big deal for them to try them on and buy them. I didn't ask why exactly they wanted to wear them." Melissa led me over to the displays of bras and panties... There were so many lacy ones, in all different cuts, colors and styles. I barely even knew where to begin when looking at all of the frilly undergarments.... I saw now all of the thongs, full-back underwear, V-backs, and all of the types of panties I could possibly own. For the first time, I was a bit jealous that I could only take a few bra-and-panty sets home today, as I suddenly was able to see myself in EVERY piece of lingerie in this store. Melissa saw my eyes light up as I studied all of the bras. I felt them and examined their cuts. I think she knew what I was thinking... (I had been suddenly turned on to the wide world of feminine undewear, and she was going to help me start my own lingerie collection... with her getting the commission of course!!) I looked at one lacey black bra with big-cups, totally in love with it but unsure what to do with it. "I love this one," she said, "And I own this one. The underwire does not dig into your bust at all. I'd really reccommend it to you. A lady always needs to have several good and reliable bras for her wardrobe." (I don't even have boobs, and now here I was pulling several black, white and other flowery bras off of the racks, and the matching panties.) "Take all of the C-cup ones," said Melissa, "This way you have one uniform size for your bras, which you can stuff with tan pantyhose later to make your fake bust!!" (Jeez, this was moving so fast...) Before I knew it, however, I had a pile of bras and panties (all still with the tags on) in arm and heading back to the changing room.... I tried on each pair, with yet more amazing sensations as the panties pulled so amazingly on my crotch. Melissa waited outside the stall, as I gave my report on the fit and cut of each panty and bra... "I really like how these look," I said, "They really flatter my lines..." (God I was sounding like a woman now...) However, with the last bra (the black lacy one) I tried to wear, I just COULD NOT fasten the clasp behind my back, try as I might. (I was already in the matching black panties). "What is taking so long," said Melissa impatiently? "Uh, I just am having a hard time with the clasp of this bra," I squeaked. "Do you want me to help," she asked? "Uh, I'm not sure." " I really want to make sure the bra fits. If you are decent and wearing panties, I can come in and clasp it for you." "Ok," I said with exasperation. Melissa came in, and gave me a tight tug as she expertly pulled my straps and clasped my black bra. This new one was the most comfortable. It sent a chill through my spine to have Melissa come back and clasp me up with my lingerie. I did not even feel weird anymore about having her see me in a bra and panties. "Wow, that one looks really great," said Melissa, "It really flatters you. Your girlfriend will LOVE you in this.' I finally decided on 4 bra-and-panty sets to purchase that I really liked. I had decided on the black set (with the black lacey bra and panties), a similar white bra-and-panty set, a blue set, and a flowery underwear set. This was enough (for now), I supposed, and I'd have plenty of lingerie options to "surprise" Ayumi with for the time being. Melissa also tossed me two 3-packs of regular white-cotton underwear panties for my "everyday" wear, and she insisted that I could start going about in these rather than in my male-briefs, if I wanted. (I took the panties eagerly.) Next, Melissa insisted that I could "stuff" my new bras with tan pantyhose, to give me a "bust." She led me over to the pantyhose display and picked out 8 pairs of the cheapest discount tan pantyhose (only 1$ per pair each).... However, Melissa also insisted that my legs in a dress would look much better with hosiery (and I agreed)... Therefore, she got me two really nice pairs of thicker tan pantyhose, and 2 pairs of black tights, plus a pair of white opaque tights. I was very excited to pick up some more hosiery.... (Now it might be a bit hard to hide all of my growing purchases and wardrobe from Brett though!!!!) "Have you thought about shoes," asked Melissa? "Do you have ladies' shoes..." "Uh, can I see what you have?" "Melissa found me a pair of large black pumps that fit me, a pair of white and pink sneakers, as well as a pair of shoes that were a cross between black-sandals and heels. She also grabbed me a pair of blood- red heels that were extremely discounted (as no one wanted them, and they were in a large enough size for me). I now had 5 pairs of ladies' footwear. (My pile of purchases was getting quite large at the front counter.) "Are you interested in makeup and jewelry," asked Melissa...? "Uh, I don't know much about makeup and jewelry," I replied... "Well," she said, "Let me just show you some of our products. Your girlfriend will really like it if you wear makeup for her, and it will really add to the element of the fantasy games that you want to do. Also, all of our makeup is on sale right now, as we can barely compete with the big Department stores." "Uh, sure," I said... "Also," said Melissa, "We also offer in-store makeovers and product samplings too. This would be a GREAT way for me to introduce you to all of our products. You could get a complimentary first-time makeover today if you really wanted..." "I can't today, I have to be at work in an hour." "I can schedule an appointment then, for you, if you want..." " Uh, I'm not sure," I replied.... (I still felt weird about being a guy, and turning up in a store and wearing dresses like it was nobody's business.) "Its ok, no pressure," she said... "Thanks, I'm not sure I'm ready for it yet." "Well, if you have time, I can just introduce you to some of the basic cosmetic products you might be interested in," said Melissa.... "Ok." "This is foundation, which you need for the basic creaminess of your face. This will make you really smooth and supple. And then, I'd set you up with mascara, eyeliner, rouge, blush, and lipstick. I would suggest these things for you to buy, and practice wearing at home." "I'll think about it." "And a makeover from me would really be helpful in showing you the right way to put on makeup. Most girls, when they put on makeup for the first time, cake it on and look like clowns or drag queens. "Less is more," in the case of makeup..... I can show you how to do it right, so you look really hot and sexy. You also have the disadvantage of not learning how to makeup and style as a young teenager, so it could help to learn from someone like me." (It was true; I was a guy, with ZERO experience of actually trying to look like a woman, and this would be the perfect tutorial to at least show me a skill I might use in the future.... Melissa's face was also expertly made up, and it was clear that she knew exactly the perfect quantities of makeup to use on her face. Also, I realized now that the makeover was the PERFECT excuse to come back and spend more time with Melissa (and I was single afterall, despite the fact I lied about having a role-playing girlfriend!!.... (I could break up with my "fake girlfriend" later, if/when when the time was right))). "Ok, fine," I said, "Maybe I can try the makeup appointment with you? I'll give it a try. And if I don't like it, I can always cancel???... I can just come in, get my makeup done for practice, and then clean it off before I leave." "Sure," said Melissa eagerly.... "The earliest I can get you in is 2:30 Saturday Afternoon." (I liked the idea of Melissa showing me the right way to put on makeup, as I had never done it before, and I did not want to look like fool for Ayumi if I eventually went that far with her. At worst, I could just come in here, let her slap the lipstick on me, and then wash it off before I went to my weekly Saturday "session" at the parlor...) "Let me also get you a perfume," said Melissa, "Petite Noir is one of our most popular and universal scents." "Ok," I said, "And I'll take all of the makeup products you mentioned, as I might as well have them to practice with." She put the tubes and containers in another bag. "Sure thing," she said... "I'll ring this all up for you, and here is an appointment reminder for Saturday. Also, here is a business card and a sales card from "Dress for Success," with our number and website." "Ok," I said. "Now let me explain," said Melissa, "As a repeat customer, this Dress- for-Success card lets you earn points towards apparel here with each purchase you make, in addition to 20% off all of your future purchases here. So this makes it very affordable for you to come back, and I really hope we see you again..... Also, sir, your total is 320$ for all of your purchases today..." "320$," I gasped... I did not have that much cash on me "It won't be as steep next time," said Melissa, "with your card. You have to watch the sales on our on-line club, and that is how you know to stock up here and not let it kill you." "Its fine, its fine," I reassured her as I pulled out my checkbook and wrote a check. My sister Rachael had also just given me that huge loan, so I felt ok with making bigger purchases in the here and now. I handed Melissa the check and cashed out.... "I can't thank you enough for how much you have helped me," I said, "And I am really looking forward to the store makeover too." "Yeah, I think you will really get a lot out of it," said Melissa eagerly. "Also, come back anytime." I grabbed my several bags of purchases and headed for the door, with the "ding" of the bell ringing as I left. As I was leaving, I saw two other lady customers entering, each staring suspiciously at the guy walking out with lots of bags clearly filled to the brim with dresses, lingerie, and makeup. Nothing was said though. (I'm sure it was not something they saw everyday.) As quickly as I could, before anyone spotted me with "Dress for Success" bags, I sprinted to my car and popped my new purchases in the trunk. I would have plenty of time later to go through what I bought, but for now, I was late for work!!!.... Yet, I was very excited now for my Saturday appointment with the cute Melissa, and later, my next session with Ayumi!!! ---- To be continued.