tagTransgender & CrossdressersThe Girls Across the Hall

The Girls Across the Hall


"Relax. Trust me. I know what I'm doing. I really enjoy doing this. You're going to love it."

As it turns out, she was right.

But, I'm getting ahead of myself, no pun intended. Best to start at the beginning. My name is Chris. I am 20 years old, six feet tall, 170 pounds. I just graduated college and was starting grad school in the fall, so I had a summer, the first one in a while, where I could take life relatively easily. I work as a teaching assistant at the university and perform maintenance work for the super in my apartment building in exchange for a break on the rent. All in all, a low stress existence.

I'm not bad looking, but I'm no male model either. I land somewhere on the scale between average and unremarkable. People who see me around campus see a normal, healthy guy. When I teach, I am comfortable lecturing in front of a large group, taking questions and driving constructive conversation. During office hours, I am attentive and helpful to the students who come for help.

There's always a "but." My "but," again no pun intended, is that I have crippling anxiety in social situations, especially with women. Which also means I don't have female friends. I have lots of acquaintances, women I see around town on a regular basis. I wave, ask how their day is going, comment on the weather. But as soon as the conversation turns to anything non-superficial about me or them, I tense up, my pulse quickens, and I practically freeze. The only thing I can think of in those situations is escape.

And so, Chris the average 20-year-old grad student is a very lonely guy. I've never had a girlfriend - the idea of talking to a woman in a social situation makes my hands shake. I was tutoring one of my female students, which was no problem at all, until she started flirting with me. I had no idea if she was just having fun or was hoping for a better grade, but it didn't matter her intentions - I went from competent instructor to terrified misfit in an instant.

Needless to say, I was a virgin, with no prospects of that ending any time soon. I became adept at masturbating with either hand - after using my right hand for a few weeks, I'd switch to my left because it felt like someone new was touching me. On several occasions, through meditation and rhythmic contracting of my groin muscles, I brought myself to orgasm without ever touching myself. That was the closest I had come to a satisfying sexual experience: I hadn't needed to jerk myself off to cum.

Having a vivid imagination helped. The vast array of women I had fantasized about was impressive. In all my fantasies I never had to say a word; the woman simply went about the business of pleasuring me. If only life was really like that, I'd think wistfully as I cleaned the dollops of sperm off my stomach.

A couple of weeks after the semester ended, a guy moved in to the vacant apartment across the hall from me. He was about the same height as me, also thin. He had brown hair that was long enough for him to wear a ponytail. His voice was a bit high and he struck me as slightly effeminate. I might have jumped to the conclusion he was gay except for the steady stream of rather attractive women that seemed to be coming and going all the time. When I was going about my day or handling bits of work around the building, I observed four different women leaving his apartment in just the first week. Lucky dog, I thought.

His name was Sylvester, but he told people to call him Sly. We met for the first time when some mail had been mistakenly dropped in my box. I knocked on his door, introduced myself, and gave him his mail. When I explained that I was the super's helper, he told me that his AC unit wasn't working very well and asked if I could take a look at it. I told him I'd stop by later.

Three hours later, lugging a replacement AC unit up from the basement, I knocked on Sly's door. Expecting to see my new neighbor I was surprised when a tall, gorgeous redhead answered the door. She looked like she was dressed to go out for a night on the town. She towered over me in high heels. She was wearing a short but tasteful aqua dress that clung to her curves rather nicely. She had small but nice shaped breasts that sat high and firm on her chest. Her red hair was teased out and I could smell a hint of perfume in the air. Her long nails and very full lips were painted a matching brownish-red, and her eye-lashes looked like tiny feather dusters. In short, she was a knockout, dressed to impress.

Taken by surprise and wanting to avoid any kind of interaction that might cause me to freeze up, I averted my eyes and said, "Hi. Is Sly here? He said his AC was running badly so I am here to swap it out."

"He stepped out, and I'm not sure when he's coming back. Go ahead in, and just pull the door closed when you leave." Her voice was smooth and deeper than I would have expected. She picked up a small clutch purse from Sly's mail table by the door, checked her face in the mirror, then deftly slipped through the doorway past me. She looked back, and her shiny lips broke into a dazzling smile. "Thanks, honey." And then she winked at me. And I was very happy I didn't drop fifty pounds of air conditioner on my foot.

I swapped out the AC, wrestled the old unit into the super's truck, went back to my apartment, took a long hot shower, and then laid on my bed, visualizing the fabulous redhead as I tried to reach a no-touch orgasm. I found I couldn't concentrate enough and ended up stroking myself to completion in near record time. Exhausted, I rolled over and went to sleep.

The next morning, I opened my door to head out for the day at the same moment that Sly did.

"Hey, thanks for fixing my AC problem. It was nice getting a good night's sleep without drenching the sheets in sweat."

"No worries," I replied. I wanted to ask about the redhead but thought better of it. That didn't matter, as it turned out.

"Sylvia told me she let you in. She thought you were cute." I turned beet red. "Did you two chat at all?" he asked with a wry smile.

"Uh, no. I, uh ..."

"She said you seemed a little shy. Don't be. She's a very approachable person." He paused. "If you get to know her."

I wanted to blurt out how badly I would love to get to know her but then I'd have to say why I couldn't and that was embarrassing to me. My male friends knew about my condition and they were kind enough not to tease me about it. Sly was not a friend yet. Nice guy, but I barely knew him.

"Is she ..."

Sly mercifully cut me off before I had to go further. "She's my sister. She visits from time to time. I'm sure you'll see her again." Part of me was elated, but most of me was terrified. She had talked to Sly about me and that meant I'd have to be polite and try to talk to her. Awesome.

I nodded my head non-committally, said goodbye, and headed out for the day, daydreaming about Sylvia. I swore I could still smell her perfume in the air.

Over the next few weeks, I ran into Sly several times. We chatted politely. He told me he had moved here to take a job in the university's theater arts department. I told him about the ecstatic lifestyle of an engineering grad student. His gig sounded like a whole lot more fun, but outgoing theater types don't mix well with pathologically shy anxiety-riddled engineers. Still, he seemed to be a nice guy. I could have much worse neighbors. Especially since I benefited, voyeuristically, from the parade of his very attractive female relatives.

Case in point: a few days after my chat with Sly, I was heading back to the apartment from campus when I spotted a tall blonde woman entering the building. She was dressed in business attire and making it look good. Very, very good. She had short hair in a pageboy cut. Part of me wanted a closer look but it would have been odd for me to sprint to catch up. Besides, there was that tiny chance she'd say something horrible like "hello" or "nice day" and I'd lapse into vapor lock, followed by hours of solitary humiliation. I'd admire from afar.

Or so I thought. When I walked in the lobby she was fussing with the lock on Sly's mailbox. Her head spun around when she heard the door. "Oh, hi." She waved me over. "Can you help me? My nails are still drying, and I can't get this silly lock open."

"Why are you trying to open Sly's mailbox?" I asked. So far so good. Nothing to worry about. Just asking a reasonable question on behalf of a neighbor to whom I quickly realized was a dazzlingly attractive woman. She was gingerly holding a mailbox key with the rest of her fingers splayed out, trying to avoid touching anything. Her nails were a shiny pale pink that perfectly matched the gloss on her lips.

"I'm Felicia, Sly's cousin. He asked me to bring up his mail when I arrived. Can you help?"

It would have been rude of me to say no, so I took a deep breath and walked to the mailboxes. She dropped the key in my hand and I opened the mailbox, reached in and went to hand her the mail. She held out her fingers again, indicating that she'd rather not grab the collection of letters and flyers. Instead she raised an arm and asked, "Could you just tuck them under my arm?"

My hands were shaking but I did my best to position the mail so that she could close her arm over it. As I pulled my hand back, Felicia turned slightly which caused my hand to graze her breast. I froze for a second, then pulled my arm back like my hand had touched a hot stove. Which would have been far less traumatic. Felicia giggled softly but said nothing.

I turned to head to the elevator and mumbled, "Bye." I was proud I got an entire syllable out. I pressed the button, and then again a few times, hoping I could escape the lobby. No such luck. I heard the click of heels behind me and a caught a whiff of familiar perfume.

"Going up?" Felicia chirped. I nodded nervously. "Me too." Well, yeah, we're on the ground floor. That means she's making conversation. Crap. There was a long awkward pause, broken by the ding of the elevator bell. Felicia stepped to the back of the elevator. I considered running away but instead bravely followed. "Could you press 3 please?" Which I did.

The ride up was a very long ten seconds. When the door opened, I stood aside to let Felicia pass. For a moment I thought about staying on the elevator but realized that I hadn't pressed another floor and would therefore look like an idiot, so I walked out behind Felicia. She stopped in front of Sly's door and carefully fished out a set of keys from her jacket pocket. She looked back at me. "Are you stalking me, young man?" she said with a big smile on her face. Humor. Great. "Just kidding. Could I impose on you to help me with this lock too?" She dangled the keys in front of me.

I nodded dumbly, unlocked Sly's door, opened the door for her and then turned around, hoping to escape to the safety of my apartment. Nope.

"You're Sly's neighbor. Are you the cutie-pie Chris that Sylvia told me about?"

"Chris. Yes. That's ... I'm Chris."

"Mmmm. I see what Sylvia likes. Thanks again for all your help, Chris. Hope to see you again soon." She gave me a sexy wink and then disappeared inside. I definitely saw the family resemblance.

I felt a little guilty walking straight to my bedroom to masturbate, but I was really stressed out and I couldn't stop replaying that wink and the sweet smile on Felicia's glistening lips. I have an uncontrollable need to jerk off thinking about my neighbor's family members. Nothing weird about that at all.

That evening, I heard a knock at my door. I assumed it was a resident, so I grabbed my toolbag and answered the knock. Sly was standing outside the door.

"Hey, good, you're here. I just opened a bottle of wine and thought maybe you'd like to join me."

"Oh. Uh. Is your cousin still here?" I really didn't want to make a fool of myself in front of my neighbor and his cousin. Well, too late with the cousin.

"Is that a condition for joining me?" Sly joked. I grimaced. "Sorry, friend, she's gone home. It'd just be the two of us."

At this point, I really could use a drink, and Sly was very kind with his offer. "Thanks. I'd love some wine." I followed Sly into his apartment, instantly registering the faint scent of Felicia's perfume.

"Have a seat." I plopped onto Sly's rather comfy couch. A moment later, Sly handed me a glass of red wine. He clinked my glass and said, "Welcome."

"Thanks." I took a long sip. Really good wine.

"So," Sly began, "you seem to be having quite an impact on the ladies in my family. What's your secret?" I very nearly spit my wine out.

"I don't know what you mean," I replied.

"What I mean is that Felicia kept grilling me about you today. What's he like? Is he single? He was soooo helpful. He seems shy. On and on."

This was really weird. "That's really weird," I said. Sly looked puzzled. "I didn't say or do anything special. I barely said two words to either of them."

"Well, it's not a huge shock. You're a good-looking guy and they are aggressive women who like to corrupt the shy and silent type." Getting corrupted by either of those women sounded good. "Did either of them tickle your fancy? Should I broker a date?"

I went pale. I took a deep breath. "Thanks, but no. They both seem very nice, but a date wouldn't be a good idea."

"Are you sure? They really seemed to like you."

"I'm sure. I don't go out with women often." Or ever.

"Well, I know you're not gay. I'd have picked up on it by now, and if I had picked up on it I'd probably have tried to make a move." He paused. "I'm gay, by the way, if you haven't figured it out."

I hadn't known for sure. Now I did. It was a little off-putting that Sly found me attractive too, but since there was absolutely zero percent chance of anything happening I managed to keep Sly categorized as "male friend" and not completely shut down.

"I just don't date much," I said.

"Well, that seems a shame," Sly said simply, and then changed the topic. We chatted for another hour about life around campus, politics, cars - normal stuff. We finished the bottle of wine and without asking he opened another. The wine was having a soothing effect on me and I started getting a nice little buzz going. Sly deftly slipped questions about me into the conversation and I had been letting my guard down and letting him know a bit more about me.

So, when he steered the conversation back to dating I was ready to fill him in a bit on my condition. Surprisingly, he beat me to the punch.

"I don't tell many people this, Chris, but you seem to be a pretty sensitive type, so I feel OK telling you. I don't date much either, really. I'm comfortable being gay, but I know that there are still lots of people who look at homosexuality as wrong or off-putting. Where I moved from, there were a lot of gay-haters." He paused. It looked like this was pretty painful for him to discuss. "I had some bad experiences, which led to severe episodes of anxiety. Add that to general insecurities and the result is a gay man who is desperate for a boyfriend but who is too frightened to go out in the world to try to meet one. Sometimes, I just stay locked up in my apartment for days at a time. Having relatives come to visit really helps."

I was shocked. I never would have guessed that about Sly. I, of course, empathized. "Thanks for sharing that, Sly. I completely understand." I paused. Talking about my condition was hard but it would be much easier with someone who lived with some of the same issues. "The reason I don't date is that I have paralyzing anxiety in social situations. I've gone to therapy for years, I'm on medication, but I'm just hardwired to totally lock up."

"You're OK talking to me, though? And you can teach classes, right? What specifically sets you off?"

"Meeting strangers in a social situation is very hard for me. The friends I have were people I met through school or work first. And they are almost all male."

"Why not women?"

"I don't know. The few times that I had a female friend and they started getting interested in me as 'more than a friend' I was crushed with anxiety. It ended the friendship. Now I'm very upfront with people - men and women - that I become friends with about my condition. It's better to set expectations correctly, and it keeps my guy friends from trying to set me up or give me a hard time about not dating."

"So, are we friends now?" Sly asked, filling my wine glass again.

"I guess we are. Thanks for sharing your situation with me. Thanks for listening to me, too."

"It's my pleasure." We sat silently for a few moments, then Sly laughed. "It's really funny, you know. You're comfortable and willing to let your guard down with your male friends but not women. It's too bad you're not gay."

I laughed as well. "Well, yes, but what about you? You're a man attracted to men but are reluctant to pursue them. It's too bad you're not a woman."

Sly smiled. "Wouldn't that be nice? If I were a woman I wouldn't have to worry about what the world thinks of my being gay. I could dress sexy and flirt shamelessly with men. And have a lot of sex."

"Have you ever talked about any of this with your sister or your cousin."

"They know," he said with an odd smile. "I have another female cousin and two other sisters. They all know."

"It's good to have that kind of support system. I'm an only child, but my friends are a huge help to me."

"It's too bad that one of those male friends couldn't also be a woman. You'd be comfortable with him and get laid from time to time." Sly had that odd smile again.

"Wow, I can't handle that kind of paradox after two bottles of wine."

"Well, let's make it three bottles. I don't have to be anywhere tomorrow morning - how about you?"

It felt really good to be able to talk about my anxiety with someone who understood. I was having a great time hanging out with Sly, so I said, "Sure, why not? As long as the riddles don't get any harder than 'the man who was a woman,' I think I'll be OK."

"No promises," Sly said mysteriously. He looked at his watch. "I promised Sylvia I would give her a call this evening. There was something she needed to talk to me about. Open the bottle, I'll go call and be out in a few minutes." He handed me the bottle and headed toward his bedroom. "Shall I tell her you said hi?"

A pang of sadness hit me. "I wish I actually could say hi to a woman like that."

"Don't give up hope. Stranger things have happened. Or could happen."

I didn't know at that time how right he was or how soon.

Sly was in the bedroom for a good thirty minutes. I was two glasses into the third bottle of wine when the bedroom door opened. I froze.

Strolling out of the bedroom was Sylvia. Her wavy red hair framed her face, which was made up much less dramatically then when I met her previously, but still very alluring. She was wearing three-inch heels, with sheer stockings under a simple black dress.

"Remember me?" she purred softly. The scent of her perfume drifted through the room. The gears in my head were grinding badly. Unless she had climbed up the fire escape or had been in Sly's room this whole time, this wasn't possible.

And of course, I couldn't say anything.

"Relax, and let me explain," Sylvia said as she sat down on the couch next to me. God she was gorgeous. I was terrified and turned on all at once. "Sly explained to you how hard it is for him to have any kind of love life because of his insecurities about openly meeting other gay men. The way he described it was accurate, but his anxiety was far greater than he told you. The insults he endured from the homophobes back home shook him to his core. Sly battled depression and mood swings and would often get so worked up that he'd pass out. He'd have wild, vivid nightmares of being laughed at, or beaten up for who he is. It was debilitating. I'm sure you understand."

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