Not everything between Luis/Luisa and I dealt directly with sex between us. He was still on his quest to be a “regular girl” so he could cut a swath through the community. He needed help. I did everything I could for him. Butch that you think I might be, I still know things about being a woman. In the recent past, I have softened up my “butchy butchness” and began wearing more female attire, make up, and accessories. This is where I gave Luis/Luisa help.
I worked with him on his wardrobe, finding outfits that make him look for girly, accentuating his attractive traits and hiding his unattractive ones. For one thing, he had a nice figure, with the exception of not having any boobs to speak of. So, we worked on skirts and pants that highlighted his waist and hips. Of course, we had to be mindful that we couldn’t let his fairly prominent cock show through, so we focused on more baggy trousers and looser dresses. Crotch padding was a necessity in some instances where the garment was more tightly fitting.
Boobs were another matter. Well, naturally, padded bras came into play but we had to be careful with anything low cut. Guys love to see cleavage, which doesn’t bode well when one is wearing a padded bra. Not having much of any boobs myself, I know THIS from EXPERIENCE. It’s not like I don’t have ANY boobs; they are just small. So, sometimes “push-up” brassieres worked for me but that was a harder job for Luis/Luisa, his having boy boobs. Nevertheless, we got to get at least some semblance of cleavage and had to let it go at that.
Now, we can’t talk about male cross-dressers without mentioning an important, possibly the most important, cosmetic issue…yes…whiskers…! Luis as Luis was fortunate that he did not possess much by way of facial hair, or body hair for that matter. Forget about a 5 O’clock shadow; Luis wouldn’t get a 5 DAY shadow. Nevertheless, the did have to attend to his facial hair.
Depilatories were harsh, waxing was even worse. What seemed to work was close shaving with a top quality razor combined with make-up. That had Luis looking like Luisa beautifully .
Luis/Luisa’s good qualities included his looks and personality. He was remarkable feminine looking even without make-up. But the use of make-up could make him stunningly attractive. He hardly new from make-up (I reference our first meeting: marginally O.K. eye make-up and passable lipstick, but not really his shade.) It didn’t take long and I had him looking not just girly but hot-womanly! He also has a winning smile and captivating eyes. We worked on his “come hither” look. Guys like to be teased and attracted–It makes them feel attractive. Luis/Luisa was a natural at that and just got better.
He and I finally had to have a talk. If he was going to go out and start picking up men, there were some things that needed to be addressed:
First, safety. Don’t screw around with sketchy guys. And just start off with blowjobs with the guys you do have sex with. Be very sure they aren’t violent, homophobic, or both. If he was going to have penetrating sex, i.e., getting anal or even giving anal, WEAR A CONDOM!
Second, safety…Everything in the first category IN CAPITAL LETTERS!
Third, if he would like, I would be his “wing girl” when he needs one. It is much safer to have a “bail-out” if some guy is giving him unwanted attention. “I’m here with my friend and she will need a ride home…no….she won’t use uber.” Will work . Or, even better, “Can’t you see that my lover here is getting jealous?” I’ll even look butch, if he needs me to. There are dozens of ploys but one needs a “wing woman” to work them.
Forth, if he and I are going to have sex…any kind of sex…while he is “playing the field”, then he needs to be tested…REGULARLY. Plus, he will need to start wearing condoms when we have sex. No more cum swallowing for me unless I know I’m safe!
Luis asked me an important question , “Lin, about this sex thing? We haven’t really had sex, you know. The best we’ve done is having you blow me and I do cunnilingus on you. I mean…SEX…well, to use your parlance…we haven’t FUCKED each other yet.”
“You know Luis,” I said in answer, “you are ABSOLUTELY right! We haven’t done that…YET! Get your clothes OFF….NOW!”
We were at my place and I was wearing my XL sports jersey and was naked underneath. I was undressed in literally two seconds. Luis took a little longer–a minute. We raced..and I mean raced…into the bedroom. Fortunately, I had kept that box of condoms that Decker and I never got a chance to use up. Separate and apart from a worry about STD’s, young Luis–like Decker–was a reservoir of motile sperm. If he was going to fuck me, I was going to do my best to keep from getting pregnant!
We had oral sex often enough to be otherwise comfortable with each other’s bodies. We started off with what we were used to, Luis playing with my vagina and clitoris–digitally, this time; and I massaged his penis, finally sucking on it, to get it hard. My vagina was wet, Luis’s cock was hard, and I slipped a condom on him. Maybe it was just my imagination but his dick seemed a little harder, the head shinier, than usual…but….well.
I rolled over, laid myself on my back, and invited him into me for sex in a “missionary position”. His sheathed penis slipped right into me. His hard cock was not by any means huge but it was of sufficient size for me to know I had a cock inside me, and one that could do the job. He began to stroke his cock in and out and I actually felt right away that I was beginning to cum. This is odd for it usually takes me quite a while to do that. Nevertheless, all of the sensations where there: the increasing frequency of “zings”, the accumulation of little “zings” into a Big “ZING”, and then POW! My orgasm hit me like a tidal wave. I actually wasn’t sure where I was–I thought I was floating above the bed. All I knew is that I had a cock inside me and it was delivering energy into my body that was indescribably wonderful.
I began to moan, and then moan louder, and LOUDER. Sounds came from deep within me, growling, groaning, and moaning that had no meaning other than I was in the midst of an orgasm. What “lady-cum” that was in me expelled itself concurrent with the apex of my orgasm. Everything in me relaxed all at once. I lay there luxuriating in the aftermath of my climax.
But…it wasn’t over…Luis hadn’t cum. In fact, he didn’t seem anywhere near doing so, from what I could tell. His eyes were closed and he was pumping away in a workman like manner and, from what I could see, unaware that I had just had an orgasm. Stroke, Stroke, Stroke…almost machine like he kept at it. Before I knew it another orgasm was upon me. I lost track of time.
Luis kept at it undeterred and unfazed. Breathlessly, I managed to say, “Luis? Luis, Dear? How are you feeling. Are you anywhere near cumming?”
No answer from him other than a low frequency, “mmmmm”. And then he did say, “Roll over, get on your knees. That may help.”
With his cock still in me, I managed to complete his request. There I was on my hands and knees and Luis was behind me pumping away. Some people say this was the original sexual position, as with many creatures in the animal kingdom, and it creates the best orgasms–something about the internal organs being aligned a certain way. I never gave that much credence ….until that day .
Luis was working his level best to achieve his own orgasm. I had a sense that he did know about mine but, for him, they were of little relevance as to achieving his own. But it wasn’t long after I found myself “doggy style” that I felt another orgasm begin to build within me. If I rated my earlier orgasms as 10 on a scale of 10, which I did, my next orgasm was not only off the scale it broke whatever was measuring it. My hands gripped the sheets partially from tension but also because I had the sensation that I would levitate from the bed if I didn’t hold on. I don’t know how long this last orgasm lasted–I totally lost track of time.
Finally, I heard Luis’s voice say in the midst of a “man groan”, “I’m going to cum, Lin! I’m almost there.! OH!”
I pulled away disengaging his cock from my vagina, turned on my hands and knees to face him, and reached up and pulled the condom off his cock. I lunged so that I captured his penis in my mouth just as it began to pulse for Luis’s orgasm. I took in every drop of it…and there was a LOT of it…Every drop went in my mouth and down my throat. I had come to enjoy Luis’s semen. It had its own tantalizing flavor. And this is form a woman who detested that male fluid not all that many months ago. Decker? Yes, YUM! Cowboy? Of course, Good. Luis/Luisa well the best but only because it was the most recent.
Luis/Luisa fell back still on his knees, supporting himself with his arms. He had, not unexpectedly, a look of ecstasy on his face and he was still breathing hard. In a way, I didn’t envy him–He had one big orgasm, I had FOUR FANTASTIC orgasms. Being a woman does have its advantages!
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Not that we had Luis/Luisa tuned up, the question was: What do we do with him/her?
I felt like a little league coach sending a kid into a game.
“Luis,” I said, “remember to keep your voice low and soft. If a you come out with any ‘man sounds’…at least at first…you’re toast. Also, remember the anti-fucking dialog, ‘I’m on my period’ generally works well or, ‘I’m saving it for when I get married…or for someone special’ might work.”
Luis/Luisa nodded enthusiastically, and asked, “What if it’s a guy I really like? You know…someone I think might like…or at least not mind…my ‘male parts’?”