Author: Calypso
Title: The Transformation of Evelyn Thomas
Part: Chapter 3
Summary: The erotic journey of a young man through transgender transformation to a new female self. 
Keywords: MF, MMF, TG, cons, reluc, oral, anal, rom, 1st

Send me your comments at calypso93<at>gmail<dot>com


CHAPTER 3

The Fifth Day

I awoke the next morning with a delicious feeling of dreamy contentment. My dreams had been erotic but oddly formless... as if my dreams, though indistinct, had been of some deliciously sensual abandon. My cock was hard and straining against the satin panties. My "breasts" felt heavy on my chest; one of the bras straps had slid down my shoulder. Hmmmm.... I imagined a hand pushing the strap down off my shoulder, lips brushing mine and then my neck, my chest, my belly... I reached down and eased the panties low around my hips, freeing my cock. I grasped it lightly and began to stroke it. I imagined the hands turning me over, gently. I rolled over, face down. I imagined the hands running down my back to my ass. I began to move, rubbing my cock on the smooth cotton sheets. Slowly at first, then faster as I imagined the hands gripping my hips, strong thighs straddling my things, squeezing them together, and a hard shaft spreading my ass cheeks and slowly, ever so slowly, penetrating me. I was breathing fast, raggedly. I was just on the edge... and then I swept over it in a wave of pleasure and abandon and shuddering spasms as I came, jetting long ropes of semen up the sheets and onto my belly. I reached hurriedly under myself and caught some of it in my hand. 

As my breathing returned to normal I rolled over, off the wet spot, and lay still for a time, catching my breath and feeling my heartbeat slow. I brought the handful of warm semen up and sat up a bit to look at it. It was unevenly colored, varying from milky white to almost clear and was the consistency of thick syrup. It had a faint acrid odor. I brought it closer, thinking of the shower the other day, and of Karen's joking comment as we went into the bar last night. What had she said... oh yes, she had "advised" me to swallow the semen of a man she was suggesting I'd be blowing... in order to avoid getting on my hair or dress. Ha ha. At the time she had probably meant it, in her teasing way, to break my obvious nervousness at my first public appearance as a woman. But now it seemed erotic and even exciting. Feeling a delicious sense of forbidden pleasure, I brought the handful to my mouth and dabbed my tongue in it. 

It tasted the way I remembered... it didn't taste bad. It tasted like being bad. And that was good. I had never been a bad or particularly naughty person, but I was beginning to see the possibilities and the pleasures that could come with the opportunities. I imagined awakening to find a cock pressed to my lips, and then opening those lips to permit the cock entry to my mouth. I thought of how wonderfully submissive it would be to lie there, pleasuring a cock with my mouth and tongue, slowly and lazily on a long sunny morning. I thought of the sublime undercurrent of control that paradoxically defines a blowjob as the most submissive and the most powerful thing that can be done to a man. Slowly and lasciviously I licked my hand clean, imagining I was doing it to a cock and to another hand, the same strong hand that had awakened my by pushing my bra strap off my shoulder, rolling me over, and pulling my panties down. The feeling of abandon and submission and control truly was delicious. 

I lay in bed for a time afterwards, my eyes closed, my thoughts wandering in that odd, slow, formless way they do early in the morning. I savored the fading glow of orgasm and the odd salty taste of semen, the feel of my satin panties bunched around my hips, the bra straps down around my shoulders, and the weight of the "breasts" on my chest. It felt good. My reverie was ended by the sound of the door to Karen's room closing... which was quickly followed by Karen's head poking through the connecting door. "Oh, good, you're up!" she said. 

"I was just going to take a shower," I said, pretending to stretch and yawn. "I'll be with you in a little bit."

"Take your time, hon... you've earned it! No big appointments to meet today. I thought we could practice a few girlish skills that you might find useful."

"OK."

"I'm ordering some coffee and fruit!"

"OK, thanks!"

Karen withdrew and I could hear her starting a shower. I threw off the sheets and stood up. The semen had dried to a crusty glaze on my stomach. I tousled the sheets to hide the wet spot and undressed, dropping my panties with my discarded clothes from last night, and then adding the bra to the pile. I peeled the "breasts" off my chest, where they had stuck with perspiration, and took them in the bathroom where I rinsed them off. 

My shower was long and hot and relaxing. I luxuriated in the hot water, followed by a good scrub all over with a pleasant smelling compound made of ground apricot pits, and that followed by a wash with a wonderfully smooth liquid that smelled like oranges. Finally I washed my hair for the first time, using a very gentle shampoo and a conditioner that smelled like strawberries and left my hair feeling silkily smooth and free of tangles. 

I stepped out and took an enormous bath towel from a heated rack. Another touch of luxury, it was warm and soft and deep and I pressed it to my face and smelled lavender as I blotted my hair carefully and then toweled my smooth body dry. I took the time to slick my hair back and inspect myself in the fog-free mirror. Still slim and milky and smooth all over. My slicked-back hair and flat chest gave me the look of a naughty naked schoolgirl. I spent the next half hour carefully and slowly drying my hair while brushing it out. The conditioner had left it glossy and thick, with a small amount of hairspray and a few minutes with the curling iron I managed to replicate Karen's work yesterday... I'm a fast learner, I thought with satisfaction. Donning the white hotel robe and slippers I walked into the room, opened the closet, and thought about what to wear. 

I had apparently ordered almost everything I had tried on the other day, and the staff had efficiently brushed everything out and hung it all neatly in my walk-in closet. I had a lot to choose from. I started by thinking of what Karen had suggested we would be doing for the day. But then I got distracted... I started thinking about how the snug grey 2-piece flannel suit with its pencil skirt would show off my legs, especially if I wore them with the red pumps for a provocative flair. Then I considered the linen green sheath dress, with it bare arms, short skirt, and dark simplicity and how it would show my white arms and red hair to advantage. Then I thought of a playful look with sandals, khaki capri pants, and a plain white scoop-necked stretch t-shirt to show off my "breasts." Or the slightly naughty leopard-print stretch mini-dress whose spandex-nylon mixture would hug my every curve nicely, possibly set off by black stiletto-heel boots. At this rate I would never get dressed. I decided I was hungry first, so I walked through the connecting door and joined Karen on her terrace where she was having croissants and coffee. 

Karen complimented me on my hair as I sat down. "Not bad, sis!" She said, appraising me thoughtfully. "You learn fast. Did you try any makeup?" I laughed, shaking my head.

"No way. I need expert assistance there before I'm ready to fly solo. After breakfast?" 

"Sure."

We laughed and chatted and snacked and sipped for an hour, enjoying the warm early sunshine and the sea breeze. We were two girls, carefree and happy. 

After an hour or so, I asked Karen's input on what to wear for the day, and also how that would fit with what she had in mind for the day's activities. We went back in, as Karen explained. Today would be "general instruction," as she called it. This basically meant practice on techniques such as sitting, standing, walking (in various types of shoes), how to respond to men, basic mannerisms and reactions, and that sort of thing. She was going to suggest different scenarios to me, based on her experience, and then walk me through appropriate responses. It sounded like fun, sort of like playing "cops and robbers," although this might more accurately termed "girls and chasers." 

We decided to go with a casual general-purpose outfit. I settled finally on a black-and-white checked wool skirt, with a slightly daring short hem that came to about an inch above my knees. It was flattering and snug, with a short slit in the back. This was complimented by a black buttoned shirt-blouse made of an amazingly soft cotton blend that had just a bit of stretch which allowed me to wear a slightly small size and enjoy the tightness over my "breasts." Then I laid out my lingerie: my fake "breasts" (the more expensive semi-permanent ones were due to arrive tomorrow by express delivery) came first. Then what? I opened my lingerie drawers and thought about it while Karen went to get dressed. My shopping the other day had left me with as many choices as had my selection of outfits, if not more: I had found the lingerie shopping incredibly exciting and erotic and had probably gone a bit overboard. They had carried selections of a variety of major brands, but Karen had also suggested some more shopping, maybe tomorrow, in person at stores like Victoria's' Secret, Frederick's of Hollywood (there was a local retailer), and an online store called Secrets in Lace. I had checked their internet sites and each was wonderful in its own way. But I had to choose now! Back to earth, Eve, I thought sternly!

I decided on slightly naughty, for the thrill of it. I started by selecting real silk stockings, nude colored, which I carefully laid out. Maybe the stretch lace top thigh-highs for tomorrow? But today's choice meant garters next. Hmmm... garter belt? Or maybe... I pulled out a simply sinful full corset in bright red satin, with attached garters. It was strapless, had all-around semi-rigid boning, and was flexible and slightly stretchy, lacing up the back and with hook-and-eye closures down the front. This will take some help to adjust the lacing, I thought excitedly as I laid it out, anticipating the electric thrill of wearing it. For panties I chose a black satin high-cut, plain and cut low in front. I was curious to see if it would full restrain my cock, which was semi-hard now from the excitement of laying out all these beautiful things. 

I poked my head in to see if Karen was dressed yet; she was, in a relaxed-looking khaki mini-skirt and blue polo shirt with laced up sandals. 

"You look like a soccer mom," I joked. She grinned. 

"What about you? Did you choose your undies?"

"Yep. But I need some help with this one. I held up the corset. She raised her eyebrows. 

"Going a little naughty, hmmm? Isn't that a waste with no one to see it?" She asked as she walked into my room. I blushed deeply, feeling the heat rise in my cheeks. 

"Well, ummm, I just thought, well, that is..." 

"Oh, it's OK, silly!" Karen exclaimed. "Half the fun of being a girl is the secret of wearing sexy underwear. It's like teasing yourself, all day. Now slip that on... right, now hook up the eyelets, leave the laces loose... here." She said handing me the fake "breasts." "This corset will look better with those nice ones we have on order." 

"Yes," I said, "but you did say that today is for practice!"

"It sure is, and it looks like you're way ahead of me! Now, got those hooks done up? Breasts in? OK, now I'll lace you up lightly at first, and you position your breasts in the cups. Got them? OK, now I'm going to tighten it." She began pulling in the laces while I sucked my tummy in. It was snug, then tight, and then it slowly squeezed me in, from my belly to the bottom of my ribcage. I exhaled as it constricted. 

"Whoa, hold it for a second," I said breathlessly. The boning held me straight upright, and I felt short of breath. "How does that look?" I asked. 

"We're headed for hourglass territory," Karen said... want to look?" Holding the untied laces she walked me to the mirror. It did give me the classic hourglass figure... I had curves! I decided I liked corsets. 

"I think that's as tight as I can stand for now," I said. Lace it up and see if you can find the tape measure. I want to know what my new measurements are, just for curiosity." She laced me up lightly, got the tape, and measured me at bust, waist, and hips.

"Well," she said, "without allowing for the corset itself, you now come in at a 38-26-38. Definitely in voluptuous territory... it looks like the corset does a better job of cinching your waist and it pushes you up a bit on the chest. Too bad you don't have cleavage!" Yes, I thought sadly, it is too bad I don't have cleavage. Sigh. 

I finished dressing, moving slowly and carefully in the strait-jacketing effect of the corset. First came the stockings, which I carefully rolled on, hooking them to the garter straps. I paused for a moment to study the seams in the mirror, peering over my shoulder and making minor adjustments until they were perfectly straight. Next the panties, which I naughtily pulled on over the garter straps. That felt a little odd, but I fantasized about being able to pull them down while leaving the sexy corset on and I wanted to see what it felt like. It didn't feel bad, just a little odd. I tucked my semi-rigid cock and my balls back out of the way between my legs, but the head of the cock hung out past the strap. I pulled the panties up tight to hold my cock head in place. Good enough, I thought, relishing the feeling of the satin as it gathered between my ass cheeks. It was the first "wedgy" I had enjoyed. 

Then came the shirt, which buttoned snugly over my bust. The black stretch cotton hugged me very nicely, the buttons displaying just a hint of gap which accentuated my bust. Then there was the skirt, which fit my hips like a second skin and nipped in around my cinched waist. I turned for a side view and admired the profiled curve of my ass in the mirror and the way the skirt brought attention to the hint of thigh I showed below its hem. When walking it would hobble me slightly, enforcing small steps and stretching tight over my ass and thighs. Finally there came the shoes. I had purposely chosen these cloth-covered 2" heeled pumps in a black and white check, apart from their matching pattern, because the moderate heel would allow me some practice in walking with heels. I had bought some shoes that had heels as high as 4", but I planned to work my way up to that. The 1" heeled sandals hadn't given me any trouble last night, I thought hopefully. I was still 5' 10" with the heels. 

I studied the effect in the mirror. I looked modishly casual, like a business executive on casual day, or maybe like a well-dressed suburban wife ready for a morning at her favorite café and a little shopping. Perfect. I clipped on a simple silver braided necklace and some matching clip on earrings. I wonder if I should pierce my ears, I thought. 

Karen liked the effect too. She spent a few minutes having me turn this way and that, and then she decided it was time for more makeup training. We spent the next hour in the bathroom, sitting on the padded chairs in front of the vanity with a towel around my neck to protect my clothing. First she had me apply my own work, under her direction. After a few miscues and heavy-handed mistakes she told me to stop and then, step-by-step, walked me through the process with precise and careful instructions. I was starting to get what she was driving at. Less is more. Hint, don't advertise. Light strokes. Color coordination was going to be a bit more of a challenge; but by lunch she had got me to the point where I could reliably apply my own basic casual colors without assistance. Another victory! I felt a sense of accomplishment and basked in Karen's praise. As she pointed out, it took most women years to get it right. I was flattered and returned the praise by commenting on her excellent instruction. I settled on casual daytime look of subdued foundation with a hint of blush, only the slightest of eye shadow and eyelashes, and a subdued color but very glossy faintly pinkish-red lipstick that would make my lips gleam as if I had just licked them. 

Since it was lunch time and the rooms had yet to be cleaned we decided to go out for lunch, making it part one of my training in how to walk and act while allowing the maids to come in and straighten up. We left a note to have our discarded clothing (still on the floor, I'm such a slob even as a girl) sent for laundering, then I put a couple of pieces of ID, credit cards, and some cash (it helped that my name didn't require any changes, although my photos might look a bit odd in comparison to the new me) as well as a handkerchief, sunglasses, and a lipstick in a small black handbag, dotted Chanel No5 on wrists and neck, and off we went. I felt nervous, but not as bad as last night. 

Karen drilled me on walking before we left the room. Take short steps. Place my feet inward of their normal path, as if walking a balance beam, to accentuate the sway of my hips, but don't overdo it. Walk flat-footed, pointing my toes downward and inward. Walk slowly to avoid breaking a sweat (and being out of breath in this corset, I thought!) This all harder than it sounds. Girls have had all their lives to be feminine, so by the time they're adults it comes naturally. 

It also seems that women's bodies are put together differently and move differently. It's hard to move naturally and un-self consciously. To simulate women's forearms, which are apparently connected at their elbows at a more obtuse angle, (they swing farther out and don't hit their wider hips when walking) Karen had me put my arms down at my sides and rotate my hands away from my body so my forearms faced forward, and curl my fingers. When carry a purse she told me to try holding it or onto the strap with one hand while letting the other arm swing free, allowing my arms to swing freer from my shoulders. Even standing still took some practice: women tend to hold their arms above their waistline. When resting my hands on my hips, I was to turn my hands so my fingers were facing backwards and thumbs forward. 
Posture was important as well. Men usually have larger and more muscular shoulders than women (duh!) and they generally hunch their shoulders forward, probably to emphasize their musculature and as a sign of aggressiveness. (This generally hadn't been a problem for me, I was forever being criticized for passivity as a man.) Women, on the other hand, tend to draw their shoulders back, it seems. Karen made me stand in front of the mirror and hunch my shoulders forward, then back. She was right. They looked noticeably smaller when pulled back. It also turned out that this also helped my arms swing in a more feminine manner. (The corset helped a lot with this, virtually forcing a perfectly erect posture.)
Apart from feminine movement, my attitude was crucial. Karen warned me not to continually look down at the ground or obviously avoid looking at people. I didn't want to make someone pause and take second looks at me... except, of course, as a compliment! Also, men are socialized to be aggressive and it shows in their walk: they tend to lean forward when they walk, as if they are pushing their way through crowds. Girls, on the other hand, are socialized for passivity and tend to yield and hesitate more when walking. Karen told me to not stride out in an aggressive gait, but to hesitate more and yield to people coming towards me. 
Last but not least there was a class on smiling... girls tend to be friendlier (according to Karen, anyway), so she told me to glance at people's faces and smile. Women and men smile differently, too, it seems. Men tend to have the classic wide, lots of teeth, nice-to-meet-you smile. Women tend to smile in a more restrained manner, with their lips closed or just part of their teeth showing, especially when meeting strangers. Also, the sides of a woman's mouth are more upturned in a smile. 

This was a lot to remember. Karen saw my hesitation and laughed.

"Don't worry, you'll do fine!" I didn't feel that way. My earlier confidence had evaporated with all the "do-this, don't-do-this" instruction. I felt like I needed a reference card to remember it all. I wanted to stay in. But Karen was adamant. After a few minutes of walking back and forth, around the furniture, and through each suite to get used to the shoes, off we went. 

We walked down the hall to the elevators. I had done this before: yesterday in my dress, and the past few days in my robe. Why was I so nervous now? We passed a couple coming out of their rooms, Karen smiled and said "hello," The lady smiled back and the man said, "Hi," back... and caught my eye for a brief moment. I gave him a smile that I hoped was suitably feminine but restrained. It seemed to work OK, he smiled back and we went on. We arrived at the elevators, pushed the button, and waited. The couple caught up with us and we chatted there for a bit and on the way down. They were on an anniversary trip to San Diego, it was their first time here, and they were having fun. Karen answered made up most of the chit chat, I contented myself with a few "yes," "no," and similar brief answers. 

We parted politely in the lobby, and Karen and I headed for the front doors. It was my first time outside the hotel since my arrival three days and apparently a whole lifetime ago. Karen had my car brought around, since she hadn't bought a car yet since her return from Korea. The parking valet checked out my legs from the corner of his eye... that was interesting; he was cute in a blond California-beach sort of way so I turned and put one leg out a bit from the other, tightening my skirt and giving him a look at my ass and silk-covered thighs with their vertical seams pulling the eye higher and higher... Karen saw what I was doing and smiled, I held her eye and winked quickly. We grinned at each other. 

The car arrived quickly; I clicked around on my heels, tipped the valet and he held the drivers door for me. Just in time I remembered I was wearing a skirt, and a snug one at that: I turned my back to the car and sat on the side of the seat with my knees together, then rotated on my ass to bring my legs in. Karen nodded approvingly. The car had been detailed; it gleamed like it was new. 

"Where do you want to go?" I asked Karen. I had never been here before, Karen had at least arrived before me and had at least been out of the hotel.  

"How about a trip to the park?" Karen asked. It sounded good to me. It was another perfect day (are there any other kind in San Diego?) so we put the top down and drove away in the California sun. 

In downtown San Diego there is a large and absolutely lovely complex of park, exhibition halls, and museums called Balboa Park. It has something for just about anyone. Lying between the enormous and lush San Diego Zoo and the enormous US Navy Hospital, large pools are surrounded by impossibly green lawns and ringed by incredibly colorful flowering bushes and palm trees set off wonderful old-Spanish colonial architecture from the turn of the twentieth century. You can walk for miles through a nature preserve, across bridges to sloping shaded lawns for a picnic, or down shaded walks under old-Spanish porticos to the an art gallery, natural history museum, and even an aerospace museum. There is an outdoor theater, a Japanese garden, an organ pavilion, and a greenhouse full of rare plants. There are even little micro-museums, like the model train gallery and a photographic arts museum. It's always populated by hundreds of people, young and old: couples strolling hand-in-hand, older folks strolling in the sun, and tourist and local families letting their kids run free. I adored it. 

We parked in a large central lot, put the top out, and got out to catch the tram. The tram was an open-air bus made to look like a streetcar trolley; it had a small flight of bus-style stairs. My skirt hiked up a bit as I climbed on, gathering tightly across my ass and thighs as I raised my knees. As I turned at the top I just caught an older man just behind me being poked hard in the arm by a woman, probably his wife... had he been watching me too obviously? I sat next to Karen; the older couple got on and the woman conspicuously directed the man to a seat as far away from us as she could get. I grinned to myself. You old dog! He was kind of cute, in an older and distinguished way. When did I start thinking of men as cute, I wondered, absently. 

We rode the tram down to the end by the old-Spanish plaza, and then got off to stroll a bit. I wasn't really all that hungry yet; probably a combination of the constriction of the corset and the pervading thrill I was feeling from the constriction, the weight of my "breasts," the tug of the garters, the swish of my silk-clad legs as I tip-toed my way along, and the tight hem of my skirt hugging my thighs. We walked for a bit, bought iced lattes from a vendor, and sat and watched the passers buy, enjoying the sun and the freedom. 

To be honest, I was regretting a bit my decision to wear a black blouse. That plus the corset was starting to combine with the afternoon sun, which was getting a bit warm. I wasn't sweating yet, but I was just on the verge. The iced lattes helped and, while I wasn't particularly hungry, we walked down to an open café and had iced tea and salads. My ankles and calves were feeling a bit sore from the unaccustomed walking in heels, it felt good to get off my feet for a little while. 

Refreshed from our light lunch we walked up to the art gallery and went in. It was cool inside and the terracotta tiles echoed with the click of our heels as we strolled about, admiring the pieces. I was turning a corner, with my head turned the other way listening to Karen chatting about something or other, when I ran smack into something firm and solid. I almost lost my balance; teetering on my heels I grabbed out, turning my head to see, and realized I was grabbing onto a tall blond man in a navy uniform. He grabbed my wrists before I could grab his shirt, and held me as I took a step back and stabilized. As I did he let go of one wrist and put his hand between my shoulder blades, transferring his other hand from holding my wrist to holding my hand, gently. I was shaking from the surprise.

 "Are you OK, miss?" he said gently. "I'm terribly sorry. My fault entirely." He still hadn't let go of me, I noted. I also noted that I didn't mind. He was tall, just slightly taller than my 5'10" (with heels); I figured him at about 6'. He had sandy blond hair cut very close at the sides and tapered to a military cut on top, and with a slightly disorderly cowlick threatening to come loose in front. He had grey eyes that seemed very soft and warm. He was big and muscular and the way he held me in his hard tanned arms I imagined he could have picked me up without even making an effort. He was wearing the Navy summer "un-dress" white uniform of a short sleeve shirt, open at the neck, white trousers, and (I assumed, I hadn't looked down since I saw his eyes) white shoes and socks. His shoulder boards said he was a Lieutenant Commander, equivalent to a Major in the Army. He had gold wings on his chest, so he was also an aviator. To me he was heavenly. With his hand gently pressing between my shoulder blades and the other holding my hand it was as if we had paused in a very slow and very close dance. My hand, cradled gently in his, was only an inch or so from lying flat on his broad chest. I was speechless. He smelled good, too. 

Karen broke the silence. "Eve, are you OK?" There was a hint of humor in her voice. 

The spell broke. "Umm, yeah, uh, I'm OK... I'm so sorry; I didn't mean to run into you like that." 

"Well, how did you mean to run into me," he asked, with a hint of a smile. 

"I, umm...  Oh! You know what I mean!" He was laughing at me. I couldn't help but giggle in return. 

As my giggles subsided, I asked in what I hoped was a sultry voice, "Are you ever going to release me, Commander, or am I your prisoner?" 

Now it was his turn to be flustered. He dropped my hand and whipped his other hand away from my back as if I was red hot. Then, not knowing what to do with his hands, he fidgeted. "Oh, geez, I'm sorry, I didn't mean to..." Then he noticed the half smile creeping up my face to my eyes. "Oh, hey, good one! You really got me, didn't you?" 

"Hmmm... maybe a little." I turned as if starting away, but looking at him out of the corner of my eye. I had dipped my head down, quickly, and the "peek-a-boo" bob in my hair was doing its thing. I peered at him from under a red-gold cascade of silky tresses. I was feeling calm, sexy, and in control. I was surprising myself. I wanted to control this incredibly masculine, sexy man. And I wanted to... well, I wasn't allowing myself to think along those lines, not yet, anyway. I felt like I could make him melt in my hands... and that I had started off well in that endeavor. Now to apply a little more pressure. He looked a bit flustered, as if he was trying to think of what to say. 

I started walking as I talked to him, carelessly and without looking at him. I knew he'd half to take a couple of quick steps to catch up and hear what I was saying; it also meant he had to follow me like a lost puppy. "So, what brings a Naval aviator into the art gallery, Commander? Shouldn't you be in the air and space museum?" I paused, pretending to look at a 17th century religious icon. I was actually watching him as he stepped quickly up to my side; his eyes focused on me and not the art. 

"Well, you know, Dave and I figured that we'd take in a little culture since we have this period of down time. Our squadron just got back from a Westpac. That's a..."

"I'm familiar with Westpacs, Commander." I was being deliberately cool. I wanted him to work harder on me. (Westpac means a cruise by a Navy battle group, usually grouped around a carrier, to the Western Pacific. They usually lasted about 6 months. I knew about the Navy from a tour with the joint Army & Navy staff at the headquarters of the US Pacific Command in Hawaii.) I noticed that "Dave" was another Naval aviator in undress whites, and that he was following along, chatting with Karen, who was apparently doing a good job of keeping him laughing. I hadn't noticed either of them for a few minutes now. My attention was focused on this one. Damn it! What was his name!!!? I hadn't been able to catch the name on his uniform nametag. 

"Oh, really, you are! Well, that's something..." he floundered a bit. Apparently he wasn't used to smart women. "Um, is your husband or, uhh, boyfriend a sailor?" 

"Oh, I don't have a husband. Or a boyfriend. Right now, anyway. And I've never dated a sailor." I let that sink in. OK, I'm advertising myself as available. Let's see if he takes the bait... and if he picks up on the mystery of a "girl" who knows military jargon and ranks without being a stereotyped military dependent or groupie. I didn't have to wait long. He was a quick study.

"Well," he said brightly, "This must be my luck day! And you're intelligent as well as beautiful!" He grinned at me with his boyish grin, which he probably expected to make me melt in the face of his masculine charm. It was having an effect, come to think about it. He was terribly attractive. 

"Oh, I have my moments," I said off-handedly. "Don't you meet many intelligent women, Commander?" I asked with a saucy tilt of an eyebrow under my red cascade. 

"Oh, you know," he said as he struggled for a `correct' answer, "most women want to talk about clothes and shopping... not that that's wrong!" he hasted to add. He realized that he might have lost me. It was funny. 

"Oh, I hardly ever talk about clothes and shopping... to a man, anyway," I said. "They generally don't understand. Do you have a name, by the way?"

"He stopped and took my hand, softly and almost formally and said, "Lieutenant Commander Peter Fitzgerald, miss...?" His eyes were a sparkling, and as he stared deep into mine I felt spreading warmth deep inside my groin and lower belly... God, I was getting hot for him! For a man! What was happening to me? This was going way beyond the fun teasing of dressing up... his hand was strong and hard and warm and I realized that I was staring, speechless. I jerked slightly and he smiled, just slightly, to see my discomfiture as a burning in my cheeks told me I was blushing. 

"I'm Eve Thomas, Commander, and I'm pleased to meet you."

"Oh, the pleasure is all mine, Miss Thomas," he responded softly... "but please, call me Pete." 

"OK, Pete," I said, softly, looking at his gorgeous eyes and feeling the warmth spread. "I'm Eve."

We walked and talked and walked some more, and my feet hurt so we stopped and Pete playfully offered to massage my feet and I accepted, much to his evident surprise. His hands were as strong and hard as I had thought at first, but incredibly dexterous and gentle as well... as he tenderly worked the flesh of my feet and toes through my silk stockings I began to feel more than warmth... I felt my small cock beginning to stir, hardening as I grew aroused by his attentions. Where was this going, I wondered briefly before Pete began to roll my toes, gently, between his fingers. Wow that felt good... I purred with pleasure, forgetting my reservations. Pete had talked about himself, about how he and Dave flew the FA-18 Hornet, about the Navy, and, just a trifle suggestively, about how hard it was to keep a relationship going but that he was still looking for "the right girl." Have anyone in mind? I thought to myself. 

Karen was having a good time chatting and laughing with the Dave, but every now and then I caught her looking at me with something like amusement. It was getting late, too, the dry semi-desert air cooling quickly. Karen broke my reverie. "Hey, sis, remember our dinner reservations?" Of course we didn't have any, but I know a signal when I hear one. 

"Oh, yeah, right!" I said, with what I hoped sounded like sincerity. Pete moved fast before I could say more. 

"Is there any way I could talk you into canceling your plans and having dinner with me?" 

Karen saved me again. "Oh, this is girls night... we've been planning it for weeks! Right, sis?" She was giving me an out. That's when I surprised her. And myself. 

"I'm free tomorrow," I blurted. Pete looked startled, as if he had been expecting the big brush off. He also looked pleased. Karen looked surprised for a moment, and then smiled. 

"Well, great!" Pete said, breaking a brief silence that had seemed to stretch out for a time. Was I afraid of rejection? A man was asking me out on a date! What was I doing?! "Umm, is six OK?" he asked tentatively. 

I smiled slowly and laid my hand gently on his arm. He twitched as if he was surprised, almost enough to jump. Was I having that much an effect? "Six would be lovely," I purred, softly, so that he had to lean in and smell my perfume to hear me. I stroked his arm, softly and almost imperceptibly, as I withdrew my fingers. He twitched again. I had no idea teasing was so much fun!

We exchanged phone numbers; he gave me his cel number, scribbled on the back of a calling card, and I gave him the hotel number, which he wrote in a slightly clichéd `little black book.' Then we said some overly friendly and slightly awkward goodbyes and parted ways. I caught a glimpse of him out of the corner of my eye as he watched my legs, and probably my ass too, as I walked away. I made sure to pigeon my steps to give him a nice ass wiggle. He almost walked into a sign and his buddy Dave had to punch him in the shoulder to get him to pay attention to where he was walking. I almost laughed out loud, but stifled it into a giggle I shared with Karen. "You know, I have to ask," she said, "do you know what you're doing? I mean, I know this is all my idea, but I had no idea you would get this far into the part... You do know he wants to fuck you, right? I mean, this is way beyond flirting!" 

I stopped giggling. She was right. This was serious. I had some decisions to make. I had never been attracted to men... and I was not and am not gay. I know that sounds weird, but it's how I felt that mattered. I felt like a girl who has been let out of a convent for the first time and feels she has to make up for lost time. I felt excited and afraid and anticipatory and apprehensive all at the same time, but in a combination that was more thrilling than anything I had ever known. "Karen," I said, looking in her eyes, "we need to talk. Someplace where we can get drinks. Maybe lots. I don't know what I'm doing... except I do know that I want to do this, and I need you to keep helping me until I figure out what it is." 

Somehow she understood my incoherence. We drove to the Old Town section of San Diego, parked, and walked to a restaurant that specialized in Mexican seafood, which I loved. Over spicy fish and margaritas we talked back and forth in privacy that was guaranteed by a balcony table with potted palms to the sides and background mariachi music. 

She felt bad, as if she had got me into something and that I was trying too hard to play a part she hadn't intended. I soothed her concerns, explaining that I felt more alive and free than I ever had. I explained how I had acted on impulse by accepting Pete's advance, but that I had truly wanted to and that I was excited and thrilled by his attraction to me... and that I wanted to continue with it to see where it would lead. I explained that I didn't feel attracted to him as a man... that I didn't feel gay, but instead like a perfectly natural sexual attraction by a woman to a man. At that she took my hand and looked in my eyes. "Eve," she asked, "don't take this the wrong way... have you ever wondered if you might be, umm... transsexual?" 

To be honest, I had. During some of my lonelier and hornier periods I had looked at internet porn, and had discovered, and visited more and more frequently, transsexual porn. At first I had been excited by the exotic nature of the transgendered women, but as time had gone by I had begun to fantasize about what it would like to be one. I admitted as much to Karen. She sighed with relief. 

"Sis," she said determinedly, "I feel better knowing that. I really do. Is this what you really want to do?"

"Yes," I said simply. I had taken the plunge. "I don't know how, but `Eve' is the real me. I want to be `Eve.' I want to stay her. Will you help me?"

"Of course," she said simply, "but it's not going to be easy." She frowned for a moment, lost in thought. "This is going to take some thought. But first, we have a date to prepare for." She brightened, suddenly. "This is going to be fun! It'll be like prom night, but with no curfew! But do you want to have sex with him?" she asked suddenly and earnestly, shifting moods in mid stride. 

I thought about my morning fantasies of semen and cock and submission. "Yes," I said simply. I was really taking the plunge for good. 

"Well," she said, "we have some work to do to get ready! I'll have to teach you how to have sex with a man... how far you can go, how to get him to do what you want, and how to brush him off if you change your mind. This will be fun! It's like helping my kid sister lose her virginity. In a sense I guess you are, come to think of it. But there are some issues. I mean, your big problem is going to be your, ummm, physical reality. I can't help you much in that area. We don't know if he's the kind of guy who would go for it anyway, or if he would be turned off... or worse yet, get violent or something. I can at least teach you how to give him a handjob or blowjob good enough to send him away happy... I'll help you with the rest too, but you'll have to feel it out on your own." 

"Well," I said coyly, sipping my third margarita and feeling the heady rush of alcohol, anticipated sex, and the sense of wickedness of it all, "I was actually planning on feeling him quite a bit. Out of his pants, if possible."  I timed it to catch Karen sipping her own drink. She almost snorted margarita out her nose, and then segued into a fit of giggles that we shared for some time. 

The first part of Karen's plan, as it turned out after we left, was at a sex toys shop. How did she know where everything was located? I was feeling a little reluctant and worried and was starting to wonder if this was really what I wanted to do. I was getting beyond second thoughts... but Karen grabbed my hand and dragged me in. 

It wasn't sleazy, like I thought it would be. It was well lit and clean and looked a bit like a video rental place, except for the truly amazing things on the shelves... as I goggled at 12-inch lifelike plastic cocks with heads on both ends and plastic models of anal and vaginal orifices, Karen made some selections. I was surprised to see I wasn't the only `girl' in the place. While there was certainly more men than women (the men generally looked like slightly furtive middle class guys - probably on business trips away from the wifey, like those two guys last night, I thought) there were several couples shopping together. I never would have guessed! 

Karen paid and we left. In the car she showed me what she had bought. First was a butt plug... a short, slightly cock-shaped rod with a firm shaft inside and covered with a "skin" that had an amazingly authentic flesh-like feel. It was about 4" long and tapered to about an inch wide at its base, with a wide flange at the bottom. Karen informed me this was for my ass (duh!) and to get me ready in case I wanted to try anal sex. She told me I could leave it in as long as I wanted to!

Next was a surprisingly lifelike dildo... complete with balls, it looked and, amazingly, felt exactly like the real thing! It was about 7" long, and 1 1/2" wide (Karen informed me that, porn stories notwithstanding, the average cock was only about five to five and a half inches long) so it would probably be more than enough for a "beginner." This, Karen said, was for me to practice my cocksucking and, if I made enough progress, to try sodomizing myself to get used to the length of cock up my ass. It was even covered in a vinyl coating that was not only velvety smooth but even had raised veins & lifelike balls! This was looking more and more like fun!

Finally there was a tube of water-based lubricant that was also a warming lotion... The instructions advised me to drizzle a little (strawberry flavored) gel on breasts, back... or ass or pussy, and then to gently rub it in and blow on it. Apparently it would make the exposed skin feel warm, sensual and tingly... all at once! I was already looking forward to it! 

I could hardly wait. Karen drove back while I daydreamed in a sensual reverie. A date... what would it be like? Would he still be attracted to me? What would I wear to make myself attractive? Would he try to kiss me? Should I kiss him back? What would it be like? Did I really want to have sex with him or was this just a kinky fantasy? Could I go through with having sex with him if he even wanted to? What would it be like? The questions and emotions swirled in my mind as we arrived at the hotel.

The front desk had good news in the form of a package. The prosthetic `breasts' had arrived. We went up to the room. I wanted to try the `breasts' on, but Karen had other ideas. "First," she said, "You need to learn about cocksucking and buttfucking so you can practice on your own. We'll start with cocksucking." Performing a good blowjob took some practice, it seemed. 

I had never really thought about it, to be honest, but now that Karen was teaching me it made all kinds of sense. My, umm, "masculine insight" gave me a bit of an advantage as Karen lectured me, using the dildo as a teaching aid. I even managed to teach her a few things as we went on. For one thing, I already knew about male sensitivity... I knew only too well that the male genitals are highly sensitive to pain. I didn't need any encouragement to be very gentle! 

But Karen went on to give me some additional pointers that I hadn't thought of, like foreplay. "Try starting by gently kissing his face and mouth before gradually proceeding to his genitals," she advised. For extra effect I was to use my lips and tongue to lick, suck, and nibble all along the shaft. She said the best technique was to start with the cock head and then move to the sensitive place where the head joins the shaft on the underside, following the seam that runs down from the head to the base. As I sucked my way along the shaft all I would have to do is pay attention to learn those areas that gave him the greatest pleasure. By continued licking and gentle sucking and nibbling along this area with my tongue I would very likely bring make him cum quickly... Karen suggested that if I wanted to please him in a hurry that I get him off like this in order to become familiar at first hand with what his orgasm would be like for any later occasions. 

Then we talked about positions. She suggested, for my own convenience, kneeling between his legs and approaching his cock from the bottom rather than from the side or the top. "Pay attention to the inside of his thighs," she advised. When I got to his cock and I had warmed him up a bit by nibbling and licking the head and shaft she told me that the simplest and nicest would be the old favorite: to simply slide my mouth up and down on his cock. Take the head of the cock in my mouth and suck it, she said, tickling it at the same time with my tongue. Slide my moistened tongue lovingly over the head until my lips closed around the shaft at the point just behind the head. 

"Don't just open my mouth and close it around his cock... slide it in!" she said with mock severity, "he'll enjoy it much more that way!" Then I was to move my lips up and down the shaft, sucking and pressing with my lips and tongue. I could go slow or fast taking as much cock into my mouth as I like. Slide down as far as I can, drawing his cock out slowly while sucking on it. Gently rasp my teeth across the skin. When he came it would be up to me. 

	"Swallow or not, it's up to you," she said. "I swallow, personally, mainly because I don't like the mess if I don't. It doesn't taste bad... a little salty maybe." (I didn't let on that I already knew this.) "It depends what he's been eating. DO NOT let him eat asparagus if you are planning on sucking his dick later! Some guys want to pull out and shoot their come in your face or hair or on your tits. That's up to you, too. It's kind of fun, in a submissive and kinky way, but it makes a hell of a mess and it really messes up your hair and makeup. Don't let him do it if you still have to go out in public!" 

Then we chatted about other methods. One was to lick upwards from the balls to the top of the cock, like a lollipop. Another was to heighten his orgasm: I should place my thumb at the very base of his cock, blocking the tube through which the come spurts so it can't escape. 

"At the same time," she said, "suck hard on the head of the cock so that when he comes it will last longer and be very intense." That sounded delicious! Karen said that this could delay his cum for several long moments... and that when I finally allowed the come to spurt it would last much longer and be more intense as a result. She said I might be surprised by the intensity of his cum... and I was looking forward to finding out how intense I could make it!

Then she told me about the warning signs that tell a girl when he is getting ready to cum. I was to watch for signs so that I would be ready in the future, like getting ready to swallow. The head of his cock might swell. He might thrust his hips forward. And for most men, immediately prior to coming, there would appear at the tiny, lovely lips at the tip of the cock a clear drop or two of fluid. When I saw this, tasted it, or felt the opening I would know that he was coming... "then get ready!" Karen said. "When he comes he may want to push your head down the shaft of his cock... he'll wants to fuck your head!" 

	Then she talked about depth of penetration. I had now idea this was going to be so complicated! One of the first things I would have to deal with would be my gag reflex. "Most men," she said, "seem to want to force their cocks down your throat as far as they can get it. Particularly when they come!" Since, as she pointed out again, the average length of my oral cavity is three to three and a half inches while the average cock length is five to five and a half inches this is a problem.  She suggested two techniques. One was position: I was to get in a position where I could turn my head so that my mouth and throat would lie almost in a straight line, probably by lying on a bed so that my head would be near the edge with my body sprawled with my head is tipped sharply back. This would allow him to enter my mouth in such a way that and so deeply that his pubic hair would press against my lips. Wow!

	The other method involved mastering my gag reflex. This would take more skill and concentration. I could overcome the gag tendency, she said, by completely relaxing my throat at moment he thrust into my mouth. "But you'll have to stay this relaxed during the entire his cock is down your throat or you'll gag!" I must have looked worried. 

"Practice with the dildo," she said, handing it to me. "But remember," she warned, "You'll only be able to relax and take his cock like this if you completely trust him. He'll be in full control. He'll do all the motion. This is one of those times you'll have to completely relinquish control to him. As soon as he can, he'll stick his cock as deep down your throat as you'll let him. Then he'll start fucking your head. If he can get deep enough into your throat it'll be like he's shooting directly into your stomach!" Wow, I thought. What an idea!

"After he comes you might need to try something else to keep him hard and interested," she said, "in case you aren't just trying to get rid of him. Most guys are wiped out by a single orgasm. It's possible to get him up again but you might have a long way to go before you can get him to come again." Cocksucking alone at this time would most likely not be enough to get him off, it seemed. Karen explained further. I would have to combine some of my techniques to stimulate the juices for a second or even third go around... which sounded really enticing, to tell the truth.

"The best part," she said, "Is that after he has come once and if you can get him up again, he'll be able to keep going for a long time... and you'll be free to really get into his body and explore all those erotic areas you missed when you were concentrating exclusively on his cock... his navel. His toes. With the second come you'll have all the time in the world." 
Then she started on anal sex which, thankfully, was a bit simpler. The key point she made was about cleanliness, which seemed like a no-brainer to be honest. Karen had three basic rules. I didn't even have to take notes. 

Rule number one was the cleanliness rule. Anything that would go up my ass shouldn't be touching anything else. Never ever take the penis out of the anus and put it into the vagina. (Karen stopped and reddened for a bit while I giggled. My what...?! OK, she made her point, but it was kind of funny. Karen seemed to be forgetting my status, much as I was.) "Basically," she said, getting back on topic, "after any kind of assfucking or fingering, you should immediately wash those parts." It sounded good to me. 

Rule number two was about lube. This also sounded like a no-brainer. The ass doesn't produce lube, she explained.  (No shit, I thought). Basically, using a lot of lube is good and using even more lube is better from a pleasure standpoint. That sounded fun, to be honest. Karen recommended a high quality water-based lubricant like the one she had bought me in the sex shop. (I was really looking forward to that warming sensation the package promised). 

Rule number three was about foreplay. This also sounded good. Three fun rules! Why wasn't school like this? (Hmmm... I was having a vision of a schoolgirl uniform...) Karen poked me. "Pay attention, silly!" She had caught me fantasizing. I was getting really turned on. My cock was straining against the panties. "Start with your fingers," she said. "Try one, see how you react, then another. Make sure he goes slow.  Don't forget the lube!" Karen suggested I start practicing with the butt plug and then work my way up to the dildo. 

Then Karen wanted to chat. I wanted her to leave the room so I could try on lingerie, fuck my own ass with the butt plus, suck on the dildo, and jerk myself off. Several times, maybe. I was thinking about covering the dildo in my own come and then sucking it clean. My heart was racing and my breathing was a bit ragged, and not just because the corset was making me breathless, either. But Karen made some good points while I fantasized... which only added fuel to the fire. What made assfucking and cocksucking so much fun, anyway? Karen liked the idea (and so did I, now that I thought of it) of being submissive while still running the show. Since communication is such an important factor (trying to make him read my mind when he's sodomizing me is an even worse idea than usual), it would be perfectly acceptable for me to give detailed instructions while lying there getting fucked. Cool! 

It's also incredibly relaxing, she said. In order for it to work, I'd have to let my butt muscles get seriously loose. In the process, the rest of me would presumably get pretty loose as well. "It's an odd sensation, relaxing into ecstasy rather than tensing into it," she said. "For me at least, sex tends to be fierce and tight, with lots of blinding white light and electricity, a bit like climbing a ladder of high tension wires. Getting buttfucked is a very different experience, more like a slow gentle dissolve into the cosmic abyss." That really did sound nice. I was really, seriously hot by this point. It was all I could do not to pull off my panties and start jerking my cock right then. 

"Also, you can feel everything," she went on, oblivious to my squirming. "Your ass is very sensitive; a lot more sensitive than your cunt, er, dick anyway, and it's really tight. Every move, every nuance, every twist and turn of the finger or dildo or cock goes right through your ass and into your brain. It doesn't take much to make you feel completely full, and it never leaves you feeling like you didn't get enough." She was still talking, dammit!

"And, last but not least, there is the submission... which is wonderful. Since your ass puts up a lot of resistance to being penetrated, the feeling of being taken, opened up, invaded and ravaged and violated or whatever, is intense... If you're able to stay loose enough while you're taking it up the ass, then by all means, go for it... play the part. Moaning and little cries turn a man on, along with demands for more and talking dirty. You might want to try a little role play while you're at it. The innocent-but-naughty girl act is always a favorite. Especially when you're being buttfucked." She noticed me squirming and grinned. "You're hot for this, aren't you?"

"Yes, dammit, and are you done yet?" I demanded. 

"Why, got something urgent you need to take care of?" She was teasing me now. I stuck my tongue out at her and, with that, she got up and went into her room, closing the connecting door. At last!

I didn't even bother undressing. I pulled my panties off in one movement and flung them into the corner and grabbed the butt plug and lube bottle with shaking hands while my cock sprang to erection, free at last. I squatted on my knees in the center of the bed and pulled off the wrapping. The butt plug was eerily lifelike in feel... like my cock, small and firm, with a soft outer covering layer. It widened to a flat flange at the base, so it wouldn't disappear inside me, and the flange had a small knob to grab onto when pulling it out. 

I squirted some of the lube in my hand, rubbed it all over the butt plug, and then ran the rest up and down in the crack of my expectant ass. It felt deliciously wet and cool at first, then... it was warming! With a hint of a tingle, too! God, it felt good! Oh, my, God.... My hands were shaking even more as I squirted some more lube on my fingers, dropped the bottle, and found my anus with a glob of lube. I gently pushed the finger, lube and all, up my ass. Aaahhh..... Ohh... it was soooo goooood... God, the warming of the lube was incredible. I wiggled my finger around a bit, enjoying the feel of it and exploring myself. I found the hard round knob of my prostate and rubbed it gently... and was rewarded with a wave of quivering sensation that almost made me collapse. Experimentally, I inserted another finger... and then another. Enough. Time for the plug. 

The plug popped in easily enough and felt wonderful in place... I felt full, like I had to shit, but it rubbed me just the right way, in just the right place... my cock was so hard you could have broken glass with it. Now for the dildo... I pulled it out of its package with fingers still greasy from the lube. Ooops... I stumbled into the bathroom to wash my hands. I must have made quite a sight... my hair mussed, my skirt rumpled up, no shoes... and with a butt plug in my ass. I washed my hands, and then took the dildo in both hands and brought it to my face. It looked like a real penis looking back at me. I held it semi-vertical, as if it was in front of me, leaned back against the bathroom counter so that the counter rocked my butt plug knob, sending more waves of prostate pleasure through me, and then began to lick my new toy. 

I did everything to that dildo that Karen had told me, and more. I licked, nibbled, sucked, and stroked it. I ran my lips up one side and down the other. I took the head gently in my teeth and tried to wrap my tongue around the head. I relaxed as best I could and tried to stick it down my throat, but gagged... so I kept trying. After a while I was able to get it in my throat without too much trouble. Karen had been right. It was just a matter of technique. But I needed some flavor...

On shaky legs I stumbled back to the bed, dropping the dildo on the bed and my skirt and blouse on the floor. In my corset and stockings I lay back on the bed, feeling the plug in my ass, and began stroking my cock... it wouldn't be long... and suddenly I was coming, hard, in long lingering spurts. Some splashed on my face and I licked the drops I could reach. The beads of semen felt warm as they ran down my face. The rest splashed my corset. I hoped it was semen-proof. I grabbed the dildo and rolled it in the puddles on my chest and corset-clad tummy, making sure to scoop up a good glob on the head. Then I began to lick it like an ice cream cone. I concentrated on technique... first the head, then the rim around the head... now the shaft... back up the underside, sucking and nibbling... then deep throating, faster and faster. I imagined his cock shooting its warm salty fluid in my mouth, savoring the lingering taste of my own and wondering what a man's would taste like... wondering what Pete's would taste like, in fact. 

But I was a gooey, sticky mess! I sat up and loosened my corset and detached the garters, allowing it to drop on the floor. Then the stockings. I simply made a pile, making a mental note to tip the maid a little extra the next day to make sure my now stained clothes went to the cleaners, and went in the bathroom for a little quick clean-up. After a shower and a little after shower splash I donned a long, red, silk nightgown and climbed into bed. The silk was incredibly smooth and luxurious against my smooth, hairless skin. I imagined Pete running his strong hands down my back as I knelt before him in red silk sucking his cock, and shivered. My calf muscles were stiff from being extended all day in heels, my feet were sore from the new shoes, and my ribs were sore from the corset, but I didn't care. I drifted off to sleep fantasizing that I was in bed with a man I had just made love to.
