Becoming His Woman Pt. 02

I woke to the smell of brewing coffee and an intense - but not necessarily unpleasant - ache in my ass. As my brain began to focus, I did a quick recap of the last 12 hours. I had been spit-roasted by two well-hung black men; the white cream, as it were, in an Oreo sandwich. One of the guys - Henry - I met two days ago; I was lying in his bed for the second morning in a row. The other - Marcus - was a recently divorced and previously straight friend of Henry, and we were introduced last night. Marcus was still rebounding from the break-up of his marriage, and was having difficulty finding someone who was interesting company on a date and, in bed, could take his immense cock.

Over drinks sometime in the last week or two, Marcus had confided in his gay friend Henry that he was willing to consider, at least for sexual satisfaction, a feminine male. At the time, Henry didn't have anyone to suggest, but after meeting and fucking me, he thought I could be a good match. While I was not particularly feminine in appearance, I basically behaved like a woman in bed - I was usually a submissive bottom. I also could take, and enjoy, VERY large cocks, which was apparently a sexual requirement for Marcus.

Marcus had been invited over to Henry's apartment, and in preparation for him, I had shaved and moisturized my body, wore a thong and thigh-highs, and put a bit of color on my nails and lips. After his arrival, and a fair amount of wine and pleasantries, we all ended up in bed, with Marcus in my pussy and Henry in my throat. While Henry has a beautiful and large cock, Marcus proved to be the biggest thing I have ever taken inside me; something like 11 inches long and extremely thick. But with a lot of lubricant and multiple hits of poppers, I took all of his cock, which was apparently a first for him. Marcus was amazed that he could be balls-deep in me AND have me begging him to fuck my brains out. No woman had ever done that for him.

Marcus had dressed and left after spit-roasting me with Henry, but took a few minutes to compliment me and express his appreciation for what he claimed was one of the best fucks of his life. He mentioned to Henry that he would call in the morning. I fell asleep immediately, but had been awakened in the middle of the night by Henry's hard-on sliding in the cum leaking between my ass cheeks. After slipping his cock into my wet still cunt while we were in the spooned position, I eventually ended up on my back, thighs holding Henry by the waist, as he took me and found his pleasure my pussy.

That mental recounting brought me to the present, just as Henry brought me a hot cup of coffee. As I sat up in bed, Henry took a seat near me and said he had something to tell me.

"Marcus called this morning while you were still asleep," he began. "He is really taken by you - he enjoyed talking to you and, I suppose it goes without saying, he REALLY enjoyed fucking you. Marcus was still blown away this morning that you were able to take all of his cock."

Henry then shifted a bit, like he was unsure how to continue. "Marcus asked if there was any chance that you would be willing to spend a couple days at his place, but first he wanted to know if it would be ok with me. I told him that you and I had just met, and that we got along pretty well, but if you were interested in his offer, I'd be happy for him and wouldn't make a fuss with you. Look, I think it is obvious that he wants to fuck you some more, but I also believe he likes you and wants to test his feelings with a feminine guy. And I'd like to see him get that chance."

Huh. I wasn't expecting this. Actually, I had half-planned to tell Henry that I needed to get back to California and that tonight would be the last for us. At least for now. But I was more than a little intrigued by the invitation Marcus was extending. Sure, there was his cock - and yeah, I could easily become addicted to having that mammoth python deeply penetrating me day after night. The way it filled and stretched my pussy was other-worldly (tho' I'm sure the poppers played a role in enhancing that feeling). And yet, the appeal of the offer wasn't just purely erotic. With Henry, I was a bi-sexual guy getting fucked by a gay man; with Marcus, I imagined an opportunity to explore my feminine side with someone who needed me to replace a woman in his life. I was thousands of miles from home; it felt like a safe place to experiment with an alternate sexual identity.

Just as this line of thinking progressed in my head, Henry spoke again. "There is an interesting caveat to his offer: He wants you to spend the day at a unique spa he found online. As I understand it, you will be pampered as if you were a woman, and will be treated to some special body care. He didn't offer many details, but I think he is still struggling with you being male, and wants you to be more feminine. He made a point of saying he doesn't expect any permanent changes in appearance, just cosmetics."

I'm not sure what surprised me more: That Marcus essentially wanted to sissify me, or that I had just been thinking about exploring that aspect of my sexuality. But the synchronicity of the two trains of thought was compelling.

"Are you ok with this?" I asked. Henry hesitated, and then quietly said, "I really enjoy you, James, but I know Marcus has had a rough time the last six months or so. After his confession to me about willing to try a feminine male, I am pleased and happy for him that he was immediately attracted to you. And while you are great in bed, I'm more into man-on-man sex; fucking you is almost like fucking a woman. I think you should consider his offer."

I REALLY needed to get back to California. And this idea of experimenting with my feminine side seemed confusing at best, and dangerous at worst. But I was inclined to do it, at least for a couple of days. Maybe I'd learn something new about myself.

So after a shower and some packing, I bid Henry goodbye and took an Uber to the spa and a previously unimagined future.

* * *

The exterior of the Chrysalis Spa was unremarkable: A nondescript storefront in a commercial neighborhood on the outskirts of Boston. But once inside, I could tell that the proprietor had both taste and money. The reception area was modern in furnishing and artful in decoration. A bright and attractive woman - perhaps trans - greeted me at the front desk, confirmed my appointment, and indicated my "treatment" had already been paid for. She also explained that I had been assigned a clinician by the name of Michelle who would oversee my activities that day. No sooner than she finished this introduction, Michelle appeared.

Like the receptionist, Michelle was attractive and composed, but had a white lab coat over her street clothes. She immediately whisked me through the same door from which she emerged and down softly lit corridor a nicely furnished exam room. There, Michelle began explaining the "treatment" I would receive.

"We have been asked - and in a moment you will be asked for written consent - to perform a set of cosmetic treatments that will, taken together, make you appear significantly more feminine. None of the things we will do are permanent changes to your body, although some can last upwards of several weeks. There will also be a bit of training - how to walk and carry yourself like an elegant woman. We will finish just before five o'clock, and a private car will take you to the address of your benefactor."

I was impressed with the spa's professionalism and comprehensive approach. After signing the consent form, Michelle instructed me to remove all my clothing, and put on a short silk robe with a beautiful floral print. She also explained that I would spend much of the day naked, or nearly so, and expressed the hope that I would be comfortable with that.

Almost on cue there was a knock on the door and I was introduced to a third staff member - Anya - whose role was to assess the best ways to make me more feminine. After asking me to remove the robe and turn around for her, she began with the basics: "For a woman, you would be tall at 5-10, but I understand your benefactor is 6-4, so height shouldn't be a problem. While you are in decent shape for a man, you lack the curves and the waist of a woman. If you were a long-term project of the spa, you would be put on a diet and exercise program; even if this is just a short engagement, we will be recommending a mostly liquid diet. And to improve your figure we will fit you with a stylish corset or bustier; it will give you a bit of a waist, push up your pecks to give the appearance of breasts, and accentuate your hips. By the way, you have a nice butt; we will give it some special care to make it even more appealing."

After a sly smile, Anya continued: "Of course, you'll get a salon treatment - shaving, depilatory, and moisturizer for your skin, eyebrows shaped, and something for your hair. Honestly, I need to think about that - since we need instant results, perhaps extensions or a wig. More hair around your face will enhance our make-up approach. It is optional, but I'd recommend a single piercing in each ear with a diamond-like stud. And we'll do your nails, hands and feet."

Anya then looked to Michelle to continue the review. "There are a couple more things we'd like to try. It would be nice if your breasts were more pronounced, and maybe your ass, too. We have a topical lotion that slows the blood flow and encourages fluid retention where it is applied. It won't suddenly give you double Ds, but it could perk up your tits and swell your butt. It will be applied several times during your stay here. We'd also like to see if we can tuck your testicles. When cold, they tend to shrink and withdraw into the body; we can make them do that and then cover the area with flesh-colored tape to hold them in. It will give your penis a more clit-like appearance."

"Speaking of clits..." Michelle said, apparently wrapping up, "starting now we want to refer to your sexual body parts using feminine terms. You have breasts or tits, a clit, and a pussy. And you should start answering to a name that, at very least, is gender neutral. The consensus in the office is that we should call you Jamie."

Wow, that was a lot to take in all at once, but it had been delivered in a professional and compelling manner, right down to the name change. I smiled and responded, "Jamie is ready to begin."

* * *

What followed was a whirlwind, but was also pampering and refreshing. It began with a measuring tape for sizing the wardrobe I would leave with. Then it was on to a cleansing enema, hair removal (leaving a triangular "landing strip" above my clit) and then a moisturizing bath, followed by skin creams and the aforementioned "plumping" lotion for my breasts and derriere. A stylist spent almost an hour putting extensions into my head hair and then shaping it into a long pageboy cut that framed my face in a flattering way. Make-up followed and I was shown a few application techniques to soften my facial features and add color to them. I was asked if I wanted my ears pierced; it didn't seem like a life-altering step - heck, even men occasionally wear ear jewelry - so I agreed. After the procedure, a pair of simple studs with fake diamonds were inserted.

Before going to wardrobe, my tits and ass were treated to the plumping lotion again; actually, it seemed like my breasts had grown a bit since the first application. I was also asked about my lips; Michelle suggested that I might want them ever-so-slightly enhanced. "Not a pair of comically large cock-sucking lips," she emphasized; just a tiny bit contoured. At this point, I figured I might as well go with it and received a set of tiny injections. I was told the effect would wear off in a few weeks.

I also spent about fifteen minutes in a clinical suite as a nurse, with rather cold hands, gently manipulated my balls and pushed them up into my inguinal canal. Then she cleverly gathered my scrotum and, using cloth tape that bore remarkable resemblance to my skin, created a shape that almost looked like labia. Interestingly, when combined with my shrunken dicklet, the final result had the appearance of a large clit standing guard at the entry to a pussy - it was a remarkable imitation.

In a plush changing room, I was shown my new lingerie and clothing (actually not much clothing). Michelle and Anya started with the corset. It was made of silken fabric that belied its capacity to pull and compress my body into a womanly shape. The corset also served to push up and cradle my tits, while leaving my large nipples exposed. Looking down, I saw that I now had a cleavage and what appeared to be large A or small B breasts. I also put on a matching thong and amazingly silky thigh-highs.

The next step was literally, a step: I put on a pair of heels - not too tall and not stilettos - and was asked to walk in them. The room had both tile and carpet, and as I tried stepping across the surfaces I was offered adjustments to my gait. Neither Michelle or Anya seemed entirely pleased, and Michelle excused herself for a minute. When she returned, she was cradling a large clear butt plug with a colored jewel on the stem. As she had me bend over a chair and dabbed a bit of lube on my rosebud, Michelle explained that the plug was intended to affect how I walked, causing my hips to sway. She pressed it into me - it had a wide bulb and narrow stem, apparently intended to be worn for extended periods of time. Once I straightened and began to walk, I immediately felt it inside me - it was definitely erotic - and it encouraged me to walk more sensuously. Both Michelle and Anya were pleased with the result.

Up to this point, I really had not been given an opportunity to see all of myself in a mirror. That changed when I was asked to walk into an adjoining room with good lighting and full-length dressing mirrors. Quite honestly, I was startled; what I saw in the reflection could not possibly be me. But it was. My body had just a hint of shape, with breasts and hips. My legs were long and luxurious in the silk stockings, and the heels helped to define my calves and thighs. But it was my face that blew me away. The hair and makeup had done their trick; I wasn't going to win a beauty pageant, but I was passable. Maybe even attractive.

Perhaps most important, it didn't feel like a costume. After the initial shock, I experienced a certain serenity; I could be the woman in the mirror. I had not anticipated this change in perspective. Sure, when in bed with my legs wrapped around a hung top, I could beg him to make me his woman. I knew what it was like to be penetrated and filled with a man's cock and cum; now I not only felt the part, but looked it, too.

I was taken through a few more "clothing options" - all, really, just boudoir-wear - and then dressed in my attire for that evening - corset, thong, stockings, heels - covered with a long coat made of a rich fabric. Even though I was basically naked under the coat, I was pretty sure my entire ensemble cost several thousand dollars. I wore no jewelry other than the ear studs, but as a finishing touch, a simple, thin choker was fastened around my neck with the name "JAMIE" rendered in sliver letters.

After saying my goodbyes to the spa staff with whom I had shared my transformation, I was put in a dark-windowed SUV and driven away to my suddenly and radically altered future.