tagTransgender & CrossdressersThe Girlfriends Across the Hall

The Girlfriends Across the Hall


Author's Note: I was so pleasantly surprised and encouraged (thank you!) by the response to "The Girls Across the Hall" that I continued the story. So, this is the second installment.

* * * * * * * *

"Hon, you gotta relax and trust me. Would you do that for me?"

If I had learned anything in the weeks after Sly moved in across the hall, it was that when one of his "relatives" told you to relax and trust her, there was a high probability that something new and wonderful was about to happen.

But, as usual, I am getting way ahead of myself. Let me back up.

Life on the floor of my apartment building remained very, well, stimulating for me after my first - well second, but first sexual - encounter with Sylvia. I still get a warm, happy feeling when I think of that night. And erect - I get very erect. The experience that Sylvia gave me was almost beyond description. Not that I had anything to compare it to at the time. Sylvia was my first. First kiss. First blowjob. First - well, I don't what the right term would be for her, so I'll just call her my first girlfriend. "Friend with benefits" was a bit too cliché and we didn't spend much time together outside the bedroom, so it was far more "benefits" and less "friend."

Not that I didn't try. Sylvia was a fascinating woman. In between the wonderful sessions of kissing, love-making, and cuddling, Sylvia would share her views on the world, life around campus, my other girlfriends - that last part was always a bit weird and requires some explanation, which I'll get to shortly.

Sylvia is the alter ego of Sly, the guy who lives across the hall from me; she presents herself to the world as Sly's "sister." I don't completely understand the psychology of it all, but other than some non-standard equipment, Sylvia is 100% female. I'm an engineer, so I have neither the training nor desire to grapple with deep philosophical or ontological questions, like "what makes a woman a woman?" But, getting to know Sylvia helped clarify a few simple concepts for me. First, we're born with a body, a mind, and, if you are spiritually inclined to believe it, a soul. The body, although a marvel of engineering and evolution, is a vastly less complex construct than the mind or soul. Reducing the nature of a person to their body is like reducing a book to the paper it's printed on. The mind and soul and essence of an individual is what defines them - the body parts are a container, a delivery system, the physical tools through which the mind expresses itself. Sylvia believes that she has the mind and soul and body of a woman. That is how she presents herself to the world. That is how she has helped me see her.

Sylvia emerges when Sly feels the need or desire to shed his natural persona as a gay man so he can more freely express his sexuality and powerful attraction to men. We live in a world where there are enough people who freely, and often cruelly and gleefully, persecute gays, lesbians, transgenders - hell ANYONE different - to the point where the more sensitive or vulnerable live in fear. For Sly, that inhumane treatment caused his psyche to create Sylvia, a very sexy and kind-hearted knockout of a redhead, as a safe place for him to have a fulfilling love life. And I was a willing and happy participant in that love life.

But, as I said, it was weird when Sylvia talked about my other girlfriends with me. Why? Because my other girlfriends were all like Sylvia.

My struggle with social anxiety, and the occasional but profound bouts of depression that came and went as a side dish to said anxiety, prevented me from having many friends, and when I was able to develop a friendship with someone where the interactions were more involved than "nice day" and "I haven't seen that movie," they were always male, and even those were exhausting. I simply was incapable of talking to women socially. It's how my brain works. Anxiety is insidious because it's so confusing. You can't talk yourself out of it, and all the "it'll be fine, there's nothing to fear" in the world will have no impact.

Fate brought Sly and I together; two souls yearning for something that their shackled and unyielding - I won't say "flawed" or "broken" because that is wrong - minds keep beyond their reach. When Sly learned of my condition, he bravely shared the extent of his with me, through the sudden appearance of Sylvia, who was free to talk about Sly in a way that Sly himself couldn't. Somehow, the symbiotic relationship between Sly and Sylvia enabled me to feel comfortable with Sylvia by virtue of their collective Sly-ness while being able to the submit to my (powerful) heterosexual attraction to the glorious Sylvia. We'd have made a great case study for the Psych department had we ever cared to share our story. Which we most certainly did not.

Through all of this, Sylvia was a part-time person. So, our friendship beyond the bedroom was limited. She knew everything that Sly did but was simply an observer when Sly was present. Her life was only what she experienced. Which is why when she talked about my other girlfriends, it was weird. She pressed me for details and then shared her opinions on what she heard. It was never mean spirited or angry - at some level she understood that the others had a purpose and a right to their time in the sun. And, frankly, not all of them were attracted to me and so I had only a passing knowledge of them. But she could be sharp-tongued when talking about the ones with whom I had become, shall we say, intimate.

In the week after I began my relationship with Sylvia, and my closer friendship with Sly, I spent two additional nights with her, learning some of the ins and outs of female interaction. Sylvia coached me on how to kiss to please both myself and my partner, and how a kiss could express feelings or intentions; for example, the difference between "mmm, your lips feel so good" and "please god, I need you to touch my cock or the ache will kill me." Sylvia liked her nipples to be played with very gently but explained, through experimentation, that other women may like it harder. I also discovered that my nipples were pretty damn sensitive. Who knew?

Sylvia was a skilled fellatrix, a word that Sylvia taught me while demonstrating her qualifications for the term. Although no experience could ever match that first time that Sylvia tenderly took me in her mouth and wove her magic oral spell around my inexperienced cock, I have been the beneficiary of her skilled lips and tongue several more times and I'd be hard pressed to say those encounters were any less spectacular than the first. She has a preferred technique - slow, gentle stimulation of my cockhead while massaging my balls. As she explained later, gentle pressure applied to my perineum - or "taint," in terms I'd understand - was actually pressing on my prostate, which further heightened the sensation. Applying pressure as I started to cum not only felt incredible, but it also had the wonderful side effect of apparently causing every drop of fluid to surge out of me and into Sylvia's luscious mouth, which she swallowed without fanfare. Odd as it may sound, growing soft between her lips as she lightly suckled every last drop out of me was possibly the most intimate part of the experience. It was tender and caring. I loved it.

On one evening, about a month after my first encounter, after she had milked me dry and released my deflated cock from her richly painted lips, she shimmied up next to me on the couch, placed a long fingernail on my chin, turned my head so I was looking straight into her eyes, and asked abruptly, "Does Felicia do it like that? Does that slut Sandy make you feel that good?"

So, yes, in that first month after meeting Sly and Sylvia I had also met two more of Sly's "relatives." I'm getting to that, bear with me

Felicia is Sly's "cousin," who I had met once by accident the afternoon before I learned about the reality of Sly and Sylvia's situation. Felicia is a short-haired blonde, who prefers the sexy businesswoman look. Sandy, as it turns out, is Felicia's "twin sister," who has long sun-kissed blonde hair down to her butt and might be best described as a California beach bunny with an appetite for some interesting (to me, at least) bedroom activities. Unlike my chance introduction to Felicia, Sandy had appeared on my doorstep one evening, with a bottle of vodka in one hand, cranberry juice in the other, a beach cover-up (barely) wrapped around her, and about a pint of blindingly shiny clear gloss on her lips, perfectly contrasting her sun-kissed, slightly freckled face.

I have been intimate with both Felicia and Sandy. For a social misfit, I had a very interesting and satisfying sex life. And Sly's "family" also seemed pretty happy. I never discussed my trysts with Sly; neither of us ever brought it up. After that night when Sly and I learned the truth about each other, any time I spent socializing with Sly involved doing the kinds of things male friends would do - except for complaining about girlfriends. We both knew that I had no reason to complain!

Unlike Sly, however, my girlfriends asked a lot about each other. About a week after Sylvia and I started hooking up for our amazing oral sessions, I ran into Felicia coming out of Sly's apartment. She wore a grey pencil skirt, a white silk blouse, and waist length black jacket. Her short blonde hair was pushed slightly to one side. Her make-up was a bit more dramatic than when I'd first met her; that first day she looked like she'd been coming home from a day at the office, but now she looked like she might have stopped home to get ready for an evening office party: business attire with a bit of sass and glamour.

"Oh, hello Chris. Do you have a moment to chat?" This was an interesting test. My comfort with Sylvia was an extension of my comfort with Sly. Would that extend to Sly's other relatives?

Apparently so. Without even thinking, I replied, "Hi. You're Felicia, right? Sure. Any friend of Sly's is a friend of mine." I cringed. Not only was that a cheesy thing to say, but it was also expressing a degree of familiarity that I had not yet earned. These ladies may inhabit the same physical space but, as Sly explained, they are different people and knowing one does not imply knowing all.

Or, as I had to remind myself as I imagined her long pink nails stroking my cock, fooling around with one doesn't mean I get to fool around with all of them.

Felicia flashed me a megawatt smile. "You're sweet. May I come inside?" she asked nodding toward my door. I opened the door and followed her in. I offered something to drink but she declined. "I hope you don't get upset, but I have a personal question for you." She paused; there was no reluctance or hesitation, she was just pausing for effect. "Are you fucking Sylvia?"

My mouth moved up and down a couple of times, but no sound came out. The look on her face clearly showed that she knew she had flustered me and was enjoying it. "It's a simple question, Chris. Are you fucking Sylvia?" She placed a hand on her slightly cocked hip and stared right into my eyes. My "flight or faster-flight" response was about to kick in. "It's ok if you are," she said with a little pout, "but I'd really like to know."

"Why do you want to know?" I asked, stalling for time.

"I have my reasons. If you tell me the truth, I'll explain why I want to know."

"I don't know that I should tell you," I said after a few moments' thought. "What your cousin and I do together is our business." I was never one for gossip - and avoided gossipy situations like the plague - and felt that respect for privacy hurt no one and was the safest response.

Felicia smiled broadly. "Sylvia was right. You are too much of a gentleman to kiss and tell. I had to see for myself." Her gaze shifted very slightly - one minute she was interrogating me, the next she was sizing me up, somewhat hungrily I might add. "It's OK, sweetie, Sylvia told me all about it. She brags to all of us about how she gives the best head. Redheads - cum hungry beasts." It was a bit of a shock to hear such crude language coming from a woman I'd only met twice, but the big smile on her face gave me to believe that she was playing. As I quickly learned, the smile meant something else. "You realize what that means, don't you baby?"

I really didn't.

"If all Sylvia has done is blow you, that means I get to pop your cherry!"

I feel compelled to point something out. I am not some irresistible guy, for whom women mindlessly drop their skirts and panties. I'm not bad-looking, and I'm in good physical shape, but there is nothing extraordinary about me. As such, you might then conclude that the likelihood that these women - as unlikely a provenance as they may have - would be actively pursuing me for sex is as big a pile of crap as those letters to the skin magazines that routinely start with, "I never thought this would happen to me, but ..." There's an explanation.

My limited understand of the nature of Sly's ladies is this: they are an outlet or an escape. Sly lives a regular life, managing the operations and facilities of the university's theater arts department. He has friends that he sees socially. Like me, he is unable to develop more intimate or romantic relationships; unlike me, whose interpersonal paralysis is an anxiety disorder, Sly's issues stem from the trauma of being persecuted as a gay man in an often-intolerant world. Sly's need for intimacy coupled with a normal sex drive created his sexual safe place: the ladies, my "girlfriends." As such, when one of the women emerge, it is to pursue satisfying a natural urge to, as my grandmother used to say, shtup.

So, if it seems like every time one of the girlfriends crosses my path she wants to have sex, it's because that is exactly what is happening. It is, quite literally, their whole reason for being. I am simply one of the hapless beneficiaries of the situation. I am pretty sure there are other ladies in Sly's orbit that I have not met, and I don't pretend that I am their only partner. What I do know is that - at least the ones with whom I have been lucky enough to experiment with - they each have a knack of making you feel like you are the only man in the world.

"Come with me," Felicia said urgently, grabbing my hand and pulling me to the bedroom. Once inside, she kicked the door shut, grabbed me by the ears, and put me into a lip-lock before I could blink. Her kisses were different than Sylvia's. More insistent, more aggressive. She bit my lip, which solicited an involuntary yelp from me, which made her laugh but not slow down at all. After a minute of kissing, I felt her nails rake up and down my pants leg. I think I was still a bit stunned - although the kissing was wonderful, the speed with which it all happened had left me still, well, not-yet-hard. Undeterred, Felicia, without ever removing her mouth from mine, deftly opened my belt, popped the button on my jeans, slid down the zipper, and reached inside. Not bothering to find the flap in my boxers, she plunged her hand past the waistband and grabbed my cock. Like throwing a switch, the touch of her hand caused a rush of blood into, and rapid inflation of, my previously soft penis. "That's it," she purred, then "Off, off, off," accompanied by rapid tugging of my pants and boxers down to my ankles. I stepped out of my pants and shorts, still wearing socks and sneakers. Sylvia tore her jacket off and threw it on the bed, unbeknownst to me grabbing a condom out of the pocket. With no pause or fanfare, she dropped to her knees and licked her lips.

And then all seven inches of my cock disappeared into her mouth in one fluid motion. I was shell-shocked. Sylvia's blowjobs had been tender ministrations, her mouth lavishly making love to my cock while her hands soothed and excited me all at once. What Felicia did was not love-making - it was an all-out assault. Sylvia had never felt the need to take me deep in her mouth like that so, obviously, I had never experienced it before. My senses were just catching up to Felicia's magic vanishing-dick trick, when my eyes went wider in amazement as her tongue snaked out between my cock and her lower lip and swished around my balls. Felicia waggled her eyebrows lasciviously at me, then almost as quickly as it went in, she slid my cock out of her mouth.

Quite the multi-tasker, Felicia had torn the condom wrapper while she had been throating me and was now placing the condom on my cockhead. Without missing a beat, she placed her lips on my cock and repeated her disappearing act, this time unrolling the condom along my length as she went. Another tongue swish on my balls, and my cock emerged from her mouth - throbbing and sheathed.

"OK," she said breathlessly, "now we're ready." She was half right; she was ready, and my head was spinning. Fortunately, with the prep work apparently done, she slowed down and walked me through what she had in mind. "Chris, I want mine to be the first pussy your cock experiences." She let that sink in for a moment. "If that's alright with you." I doubt she meant that last part - I'm pretty sure this was happening whether I was alright or not, and I imagine that was exactly the state of mind she wanted me in when it happened. No time for thinking, or hesitating, or doing anatomical checkdowns. Felicia was a woman, a woman on a mission, who was going to guide my cock into her pussy. "Just follow my lead and enjoy the ride."

She bent over the bed and reached back, without looking, to find my cock. She raised her skirt barely an inch and then let it fall down atop my cock like a shroud. I felt it nestle between what felt like two soft warm pillows. Apparently, she had not being wearing anything beneath her skirt and, as I would learn a moment later, she had already lubed her pussy. She came prepared, with a very specific agenda in mind.

"Deep breath, baby," she said over her shoulder. I complied. "And, exhale." As the air left my lungs, she pushed herself back into me. Or should I say she pushed herself back and I went into her. A long feral moan escaped Felicia's lips. "Yessssss." All my brain was saying was, "Owwwwww." I would never in a million years, while servicing myself, have grabbed and squeezed my cock half as hard as it was getting crushed by Felicia. I couldn't imagine anything so tight. I imagined I was getting strangled.

Felicia rocked forward, and my cock began to slip out of her. Before it escaped - that was the mental picture for me - though, she leaned back into me and I was once again a prisoner, even deeper inside her. "Ooooooooooo ..." she cooed. That moan made me realize just how much she was enjoying this. And that was a new sensation for me. I had always been a passive participant when Sylvia pleasured me with her lips. With Felicia, now, I was part of the action. Sylvia made contented sounds when she sucked me and swallowed my cum. Felicia was getting seriously turned on. By my cock. Inside her. This was a whole different thing.

Typical guy that I am, I grossly overestimated my role in Felicia's pleasure. Maybe someday, after years of practice, I'd perfect a technique and body control that would enable me to drive a woman wild with just my expert cock wielding. This was not that day. The moment I started thinking about what I was doing and trying to be a more active partner in this dance, I zigged when I should have zagged and popped right out of her. Half laughing, half exasperated, Felicia reached behind her, without ever raising her head, found my cock and guided it back inside her. "Easy," she said. "Relax and enjoy it."

"Relax and enjoy" was a recurring theme with the girlfriends. Years of watching porn had led me to believe that sex was a feverish and sweaty undertaking, with lots of grabbing and pounding and panting. I had much to unlearn. There was a side to sex that is grossly underrepresented in online porn: sensuality. I was rapidly learning that taking things slow and savoring each sensation was an unbeatable approach to sex. Not that I had anything to compare it to, in the first person at least. Still, I was pretty sure I was experiencing something very special.

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