Research and Analysis - Crossover 08

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Tawney/lLin helps her tranny. All's Well that Ends Well
5.3k words
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Part 8 of the 10 part series

Updated 06/11/2023
Created 12/30/2021
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So, here I was, mere weeks from facing famine, in the midst of a feast. Tanya, Cowboy, though not a regular affair, met with me often enough to count as significant in my sexual life. Juliette and Glorietta, and I got together whenever they were in town--O.K., so not that often--still when we were together we had more memorable sex, to say nothing of the fact that I loved them both. And now Luis/Luisa was on the scene to provide me with a fairly consistent availability of sex.

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!

***********************

************************

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'?"

I put a damper on that one, "Luis! Not until you get to know the guy really well! Even then, you're going to need to go slowly. First night...first date....NO WAY! Think BLOWJOB!"

"Blowjob?, he questioned, "ah, si, si, mamada.:

I was beginning to wonder if he had ever given one. Well, one way or another, he was about to find out.

Luis thought for a moment and asked, "But what about some girl hitting on me? I mean YOU did! What then?"

"Look, Luis, " I started in, "I'm going 'butch' with you so, if some girl hits on you that you don't like you can just look at me and I'll act like a possessive dike. If you like her, just give me a nod and you're free to play...BUT...go slowly...she might not entirely appreciate cross-dressers. Lots of girls do think cross-dressing guys are fun, or at least don't mind...if the 'equipment' is useable, that is...well...rather like the way you and I worked out..."

Something else occurred to me, so I told him, "Luis...remember you are NOT a hooker. You are dressed attractively and would like to hook up with somebody but you're NOT acting like a hooker or, if someone thinks that's what you are, you slap him and break things off...Got it? I don't want the vice cops hauling you in. That would be one hell of a thing to have to explain, wouldn't it?"

So, off we went to "the club".

There are easily 500 clubs in this city and, on a raucousness scale of 1 to 10, "The Shag" was a 5. It was a good pick up place; that's what the owner, and Brit, had in mind when he named it. You know, "Shag" is Brit-speak for "Fuck"! It was too hip to be a dive and it wasn't hip enough to attract the upscale loonies. I'd been there before. It was a fun place. If one wanted to get laid, one had a pretty good chance...sexual orientation notwithstanding. That's why I liked it.

It was an triangular shaped bar with the apex pointing into the room. On one side the lights were kept lower and the mood more intimate; on the other side, the lights were, if not brighter, sparkling, colorful, changed hues regularly. The latter was the dancing side, often to a live group. The acoustics of the place actually kept a lot of the "noise" from the lively side from bleeding over to the intimate side. Whoever designed the layout was a genius.

We started out on the "hot" side of the place. Lots of activity, lots of music, lots of pairing up for dancing, and lots of loud chatter. One had to talk loud to be heard over the music and other chatter. It was a mixed crowd, too. College people were there in abundance; professional looking adults ...such as me...were there; and lots of just ordinary folks, as well...all looking for a good time and maybe a sexual liaison..or two. What was missing were the bikers, shit-kickers, and general low life. The owner made sure of that or, rather, his two football linemen that he hired as bouncers did. No rough stuff was permitted in the bar or the parking lot.

Dowdy, as the owner was known, kept an eye out for hookers, too. He knew he couldn't keep them out but he made sure if he spotted any solicitation, the party or parties, were quietly escorted from the bar. He knew most of the "working girls" in the area, anyway and they steered clear of "The Shag" but that's not to say that Dowdy might not hand out a number or two of theirs on the sly...for a good customer, you understand. Dowdy was just as pleased with that arrangement and the girls were grateful...if you get my meaning.

Luis/Luisa and I, in my butch mode, were having a good time on our own. There was fun in the air and good feelings all around. I was being chatted up by a friendly but borderline obese woman...pleasant but not exactly my preference. Luis/Luisa was in on this conversation for a while but eventually was caught up talking to a couple of rather good looking guys, probably somewhere in their 20's. I'm not sure what happened but they left to do more "prospecting'. Luis/Luisa told me later that he/she shut them down because they suggested a "threesome" and offered to pay for it...a definite no/no!

Luis/Luisa started up a conversation with another young fellow and they migrated from the loud side of the bar to the quiet side. From where I sat, I could see them both and it looked like a pleasant, friendly conversation; there were smiles and laughter from them both, in addition to some touching of hands--a sign of budding intimacy. After quite some time, perhaps an hour, Luis/Luisa came over and told me that he/she was going to leave with "Chad" to get something to eat. I gave her the go ahead.

Luis and I have each other on our cell phone trackers so I felt much better with him leaving with "Chad". Even if she couldn't "911" me, I could always call her or, at least tack her whereabouts if she didn't check. Luis and I also agreed that, if we were separated, to call each other the next morning for a status report. Chad looked nice enough and Luis didn't look worried either as Luis or Luisa.

Not long after Luis left the bar, so did I. My butch look wasn't attracting anyone I'd want to play with and I honestly was feeling tired. There was a lot of tension in me from having the Luis watching duty.

I went home, got naked, and sat down in a luxurious warm, soap-bubbly bath. I had my "professional grade", deluxe, multi-speed, multi-function, pulsing-oscillating-vibrating, flesh-like, phallus shaped, female pleasure tool in the tub with me. In only 45 minutes, I had my self mellow and sleepy. So, off to bed I went--thinking of Decker, as usual.

************************

***********************

Luis called me the next morning. He was all atwitter about his night after he left the bar with Chad. It turns out that Chad really is the nice guy he seemed to be. Luis reported to me that he and Chad had a late evening meal, after which Chad drove Luis/Luisa home. He/she and Chad sat in Chad's car and talked for quite a while. Chad initiated some light kissing...which became heavy kissing. Juices flowing, Luis/Luisa decided this was the moment. He/she unzipped Chad's trousers, slipped them down over Chad's hips along with Chad's tightey-whiteys, and went down on him. Almost instantaneously, according to Luis/Luisa, Chad shot his load into Luis/Luisa's mouth. Luis/Luisa, being a gentleman/lady, forthwith swallowed Chad's semen, savoring it to the last drop. Chad and Luis/Luisa then parted with a promise to see each other again. At the very moment Luis/Luisa was talking to me, he/she reported being alerted to a text from Chad!

The question of whether Luis/Luisa would be as good of a cocksucker as he/she was a pussy-eater had been answered. I felt happy for Luis/Luisa and just as happy for Chad! But I wondered, perhaps worried, that my rollicking sex with Luis might be a thing of the past, or at least diminished. "Ah, time will tell," I said to myself.

********************

********************

Cruising through the headlines on my home page, I saw the following story:

BOMB PLOT THWARTED BY MISSING WAR HERO!

In essence, the story reported that yesterday an anonymous tip had lead to the discovery of a plot to detonate a large quantity of explosives in a densely trafficked area of a mid-sized southern city. A political domestic terrorist who's street name was, "Gorgon", was officially identified as one Decker (NMN) Smyth who had gone undercover to infiltrate a cabal of domestic terrorists. Mr. Smyth, who had been awarded a Silver Star, the third highest military decoration, had previously been reported to have mysteriously gone missing more than a year ago. Eleven co-conspirators have also been located and arrested. The bomb, if delivered and detonated, would have caused dozens--if not hundreds--of casualties! A photo of Decker was shown next to the article. The man did look very much like Decker but he was sporting a very thick, very black, beard...almost theatrical. That was the same face I remembered of that person who passed through the reporter's TV shot many months ago. Oh, Decker!

Shocked is not strong enough a word to convey the meaning of reaction. Neither are stunned or staggered. I was leveled...literally. I fell to my floor with a sigh of relief deeper than a moan.

"YES! Yes, yes, yes, YES!" What could be more wonderful!", I said out loud to myself.

Now I looked back at my display to see if what I thought I read was actually there. It was; my mind wasn't playing tricks on me. I read through the article again. It was all there...and Decker's name was still there, too. My heart soared.

The next headline was:

BOMB PLOT HERO MISSING!

If the last story had brought me to my knees, this one floored me.

It reported that Decker (NMN) Smyth, decorated soldier, who had been missing for more than a year before his successful efforts to defeat a domestic terrorist bomb plot, has gone missing again. It is unknown whether he has gone missing of his own accord or, whether authorities had sequestered him to avoid possible retaliatory action from members in the terrorist group. Confidential sources have intimated that the latter may be the more likely situation.

These stories caused a sensational series of stories. Who, What, When, Where, Why and How were explored and written about to a frazzle. The old stories about Decker's disappearance were resurrected and hashed over again and again. I was interviewed by law enforcement and by the press. I told them I had no idea of any reason, other than his PTSD, why Decker disappeared, and I had no idea whatsoever how he came to be in a position to foil the terrorist plotting. I met with Decker's father and his legal team and told them exactly the same thing. It took a lot of time for the furor to subside. It never did entirely but the level of interest gradually waned and my life went back to normal...well not exactly NORMAL.

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