A Cyber-Awakening


This story is based partially on an online chat I had once with a real person, who will remain nameless for the sake of privacy, when I was back in college. The woman in the story showed me a new side to myself and my sexuality that I had never known existed until I met her online. I will be forever grateful to her for taking me under her wing, showing me a new world, and opening my mind forever.

I was sitting at my computer in the dorms. My roommate was going to be gone for another couple of hours at least, since his girlfriend from back in our hometown was visiting and they had gone out to catch dinner and a movie. I had just gotten back to the room, finished up all my work, and the dorm seemed pretty empty, so I decided to lock the door and log on to a sex chat site I hadn't visited for a long time.

So I know what you're thinking – why get on a sex chat site when I was at a university full of young, hot women? Well, the girl who had been flirting with me was out at some sorority meeting and none of the guys next door that I usually cause trouble with were around to back me up today. I figured, why not check the chat site out, even though I hadn't been to the website in a while. Really, there was no need, considering how many beautiful girls there were in college . . . but for some reason, I chose to log on that night, and it changed my life forever . . .

My login name was nothing special, one of those typical names that tried to take advantage of the fact that I was a young and virile college guy and that I figured most women would go for that sort of thing (pretty naïve of me to think so, but I was in college!). I just hung out in the lounge, randomly chatting with the regulars and checking my email at the same time. I didn't really figure I would have any luck, as it seemed that the ratio of guys to girls on the chat site was not in my favor, plus most people seemed to be busy already.

Suddenly, this canary yellow private message popped up unexpectedly, from someone called "Hiti."

"Hi." A nice, simple beginning . . .

"Hi. How are you?" – I replied to her.

"I'm good. You?"

"I'm okay, just hanging out here for a while. It's been a boring day."

I took a look at Hiti's profile. I had no idea what "Hiti" meant – for some reason, I thought maybe it was a drink or something . . . no, that's a Mai Tai. . . . In any case, her profile told me that she was a 28 year old woman from Italy, and said "looking for younger guys" in her description, but not much else. Well, whoever she was, I figured that I might be able to have some fun tonight after all if she was really into younger guys!

"How old are you?"

"19. Is that okay?"

There was a brief pause.

"It's perrrfect." Thank goodness.

"I'm glad, Miss."

"I like younger boys. I'm 28."

"Well then, I'm happy to be a younger boy." I meant it – I'd always had a thing for women just a little older than me. I didn't really like being called a "boy," but somehow when she said it, it didn't really rub me the wrong way. Felt strangely appropriate. Who knows why.

"Where are you? What do you look like?"

"I'm in NC, in the U.S. I'm 5'9", 160, fit, golden brown eyes, jet black hair."

"Mmm, that's nice. I'm in Italy. I'm 5'8", 135, brown eyes, long black hair, 36c. People say I'm cute."

"Wow, you sound really beautiful." Yeah, good line buddy, real creative, I thought to myself. At least I hadn't said 'a/s/l' – had to give me credit for that!

"Thank you. You're sweet, baby. Are you alone?"

"Yes, for right now, my roommate's gone."

"Mmmm, I wish you were here, baby. We could spend some time together."

"Wow, that would be nice." She sounded really hot . . . of course, what did I know.

"You could be my boyfriend, we would have so much fun, we could go see everything there is to see here. You could stay at my place, if you didn't mind my sister being around."

"That sounds like a lot of fun. I don't think I'd mind living in Italy for a while!"

"Mmmm, she might even join in with us. You are sure it's okay that I'm older than you?"

"Yeah! You sound absolutely gorgeous. I'm just glad that you are fine with me being younger!"

"I like the fact that you're young. It means you are still more open-minded than most."

Hmm, I thought to myself. She sounds like she's one of those kinky types. Surprise surprise, at a sex chat site! A forum for open-minded people.

"So, what brings you here?" I wasn't being very creative tonight . . . I kicked myself for not even being able to come up with snappy lines even at a chat site.

"I just wanted to meet someone nice like you. Have you been to Italy before?"

"I went once with some friends, it was really nice. I wish I was there where you were now though."

"I wish so too. It would be nice. I could let you stay in my bedroom. Do you think you could visit?"

"No, I wish I could, but I don't really have the money."

"Oh, I wish I could meet a nice boy like you sometime soon."

We talked for a while about random things; she mentioned how close she was to her family, I talked about college, and we both felt pretty comfortable talking to each other after about a half an hour.

"You are so much fun to talk with, baby."

"You're pretty cool yourself, Hiti! I wish I had met you before."

There was another pause.

"Would you like to be with an older woman?"

Would I? Did she have to ask?!? "I think that would be nice . . ."

"I wish so badly that we could be together. But, I have to tell you something first. You have to promise to stay."

"Why would I not want to?"

"Please promise."

"Okay, I promise." A little weird, but she had been so cool up to this point that I didn't really care . . .

"I'm not like other women."

"What do you mean?"

I didn't really get to find out at that point, as she began to type in a fury and her messages came fast, one after another.

"Mmmm, baby, I want to kiss you so bad . . ."

"Oh please, you know I do too, Miss."

"We would roll our tongues around in each other's mouths, we embrace, hold each other tight."

"I feel your luscious breasts laying against my chest."

"I would set you down on a chair, as I started to dance in front of you, slowly, seductively. I begin to strip off my blouse, and you can see my tits fall out in front of you."

"I take your tits and massage them with my hands, taking the right one and licking around the nipple with my tongue, sucking the nipple into my mouth and playing with it in my mouth, as I gently roll and cup the other."

"Mmmm, you are so good baby."

"I run my tongue around your breast in circles, between your tits, everywhere."

"I push you back against the chair, and I run my leg up your thighs until I brush against your cock still inside your pants."

"When you touch me, I moan softly in response . . ."

"I begin to strip off my skirt, doing a lapdance in front of you, do you like that?"

"Yes Miss, I do, please don't stop."

"I am in nothing but my panties, and I stop and lean down in front of you and stare into your eyes. I undo your belt and strip off your pants, then tell you to take off your underwear."

"I do as you say, taking off my underwear and sitting back into the seat. My cock jumps out, throbbing and hard."

"Such a good boy. Mmmmm, you have a nice cock. A nice, boyish young cock. I lean into you between your legs and start to suck on it. Licking my tongue all around your cock and balls."

"Unnnghh, I groan and put my hands lightly on your head." As we chatted, I furiously started stroking my cock in front of the computer.

"I take you completely in my mouth, and I feel you hitting the back of my throat. I want to suck down all of your cum, will you cum for me baby? Are you touching yourself?"

"Yes, please, I just want to cum for you. I'm touching myself. Please let me cum in your mouth . . ." I was stroking myself off hard and without abandon. Whatever she said to me at this point would just make me hotter . . .

"Then, I stand up. I take off my panties so you can see me completely naked. And in between my legs, look closer . . ."

"I look at you like you tell me to, looking between your legs . . ." I played along, although I was sore that she had just stopped with the oral play all of a sudden.

"What do you see, baby?"

"I see . . .?" I didn't know what she was getting at . . . but then, just before she said what she was going to say, I sensed it . . . she was talking about . . .

"A cock. You see my 7 inch uncut cock in front of you, hard and right in front of your face."

I was in shock. I stopped what I was doing, and just stared at the computer screen. She has a cock? I thought to myself. Even though it felt like a surprise, somehow, I had guessed what she was going to say before she said it though . . . and, what was more surprising, is that my cock gave a slight, almost imperceptible, but strong twitch when she typed the word and it appeared on my computer. Even though I had stopped touching it. What was going on with me? She had a cock, and I was still hard? I was straight. It must have been something else, I must have just been excited already and it had built up inside of me . . . yeah, that was it . . .

"A . . . a cock? But how . . .?" I asked.

"I'm a transsexual. Or a shemale, if you have heard of that. Baby, I want you so bad, please don't let this stop us. I trust you and know that you are open-minded enough to accept this and be okay with it. You know that I will make it okay for you, but you don't have to continue if you don't want to."

I didn't know what to tell her. I just froze when she told me she had a cock, and everything in my mind told me to stop, that it wasn't right, that I was straight and that this wasn't something I wanted to do. But my body seemed to hint otherwise. My cock was still hard, hard as a rock, and twitching everytime I saw something typed on the computer by this mysterious woman, Hiti. Or, transgendered woman, that is.

Suddenly, I heard the door being unlocked to the room. "Shit," I thought to myself, how could my roommate be back so early when the movie should have started just an hour ago? I quickly pulled up my pants and minimized my chat window on my computer so that he couldn't see it.

I typed a short message to Hiti . . . I should have just cut off the web site, but something deep inside me couldn't let that happen. My body, I could swear, was still responding to her . . . despite her cock . . .

"Hiti, my roommate's back . . . but, are you going to be here tomorrow? At the same time maybe?"

"You don't have to lie, baby. It's okay if you don't want to talk to me anymore. But I really really want you . . . you make me feel good baby, I want to do the same for you. Please be open-minded baby. I want you so bad, and I know you want me to. Don't resist it, it's all okay."

She really knew how to push my buttons. "Hiti, I'm just not sure, I'm straight and I don't like cock . . ."

"That's okay baby. Just please stay, I want to show you a good time here. You don't even have to talk about my cock anymore baby."

"I can't, not now. My roommate's back. But . . ." I hesitated.

"But what baby?"

"I really want to talk to you again. Will you be here tomorrow, at the same time?"

"Yes, I can . . . will you really show up?"

"I will. I promise."

"Okay, baby. I'll see you then."

We both signed off, me with the bluest balls I'd ever had in my life, and with my roommate just hanging out in the room telling me how much fun he had had with his girlfriend and how they had skipped out on the movie so she could go shopping with her sister in town.

Yeah. That figures. Just my luck. Though maybe he had saved me from an experience with Hiti . . . whether or not that was a good thing, I could not tell at this point, because I still had a raging hard-on . . . that might have actually grown harder when she mentioned the word cock . . . but I couldn't let myself believe that for a second. Not a straight-shooter like me.


My roommate had class this evening, so I knew I had a few hours alone tonight to talk to Hiti if she really did show up when she said she would. My mind was still reeling from the night before though, and I couldn't focus on any of my classes. I kept on thinking about what she said . . . "A cock. You see my 7 inch uncut cock in front of you, hard and right in front of your face." It was just unbelievable. I had no idea how I would react if I had been with a woman in real life who had suddenly revealed something like that to me.

I was still very unsure about why I told her I would talk with her again. Several times throughout the day, I had convinced myself not to get back on the chat site that night. In my head, something kept on telling me that it was wrong, that she – or he? I didn't even know at that point – had a cock, and that I shouldn't be messing around with that. I practically denied to myself that, despite the fact that she had mentioned her extra surprise between her legs, my cock had still remained hard and had in fact become a little harder.

But it was like she said.

"Don't resist it."

And I couldn't.

Somehow, she had hooked me, cock or not, transgendered girl or not, and I knew there was nothing in the world that was going to keep me from meeting Hiti back on the website. Nothing. I could only tell myself, firmly, that we wouldn't talk about her cock anymore, and that I would just have a hot chat with her as if she was just like any other woman, because for all intensive purposes she WAS like any other woman except for seven inches of her body. I mean, when you think about it, it's not that much of a person's body, right?

Of course not, I told myself.

When the evening came around, I checked to make sure that the door was locked to the room and that I had plenty of time before my roommate was supposed to return. A good three hours were left before he finished all of his late classes for the day, so I had plenty of time. I logged on, fast, focused, and searching desperately for Hiti . . . I felt a very anxious feeling that I might not meet her again, that I should have somehow tried to stay on last night and talked to her more, that I had blown my chance at something . . . something wondrous, something new and different, but something frightening at the same time. Why did I feel this way . . . she was just a person on a chat site . . .

I sat there for a few minutes, then I spied her. I sent her a private message.

"Hey Hiti. Are you there?"

There was no answer for a couple of minutes.

"Hiti? Please be there . . . I really want to talk to you." I was beginning to freak out – I couldn't understand why I wanted to talk to her so bad, but there was some powerful feeling of connection that I had with her now . . . I couldn't understand it, nor could I ignore it. Even though I wanted to.

Then, after a short wait . . .


"Hiti! I'm so glad you're here. I was getting worried!"

"Hey baby. So you actually came back?"

"Of course. I wouldn't miss it for the world. :)"

"I thought that you might not show up . . ."

"But I'm here now."

"Good. Because I wish you were here with me right now. We would have so much fun together, making love."

"I think so too." I said that even though I had no idea what to expect. She was making me forget what she said last night . . . perhaps I could just brush it off as a figment of my imagination? Only time would tell . . .

"Take off all your clothes. In real life."

"My clothes? But . . . why?" I had never done that before for a sex chat, and didn't want to get caught now if my roommate just decided to skip class.

"Please, baby trust me. I want you so bad, can you do this for me?"

Again, there was something about this mysterious woman . . . I just couldn't say no. "Yes, Hiti. I trust you."

"Then strip naked for me now, and start touching yourself. You will feel so good."

"Yes, Hiti."

I felt like she was guiding me, taking me somewhere I had never been before. I felt reassured by her words, even though she was miles away in Italy. Her control over the situation was amazing, and her tenderness towards me, even through cyberspace, was unmatched.

"I am taking off all my clothes also. You see my full breasts as I lean into you and kiss you long and deeply. I wrap my arms around you and start snaking down your body."

"Mmmm, Hiti, you're so good. I encircle you with my arms and hold you close, until you start going down, down, down . . ."

"And my lips are level with your cock. I look into your eyes, and you know it will all be okay, because you see a beautiful woman looking back at you who will take care of you."

I believed her too.

"I take your cock in my mouth, you feel my tongue flicking over its length, as my hand reaches to play with your balls at the same time. You've never felt anything so good before . . . I play with and harden your meat until you are harder than ever, licking up and down your cock, sucking it into my mouth and letting it touch the back of my throat, suck in and out, in and out . . . how big is it, baby?"

"5 inches. I run my hands through your hair, pulling you in closer to me, enjoying the sensations of your mouth wrapped around my cock."

"I let you fuck my mouth with your cock, and I can taste your precum. I can feel you boiling inside . . . for me. Then, I stop."

"I look up at you, confused at why you stopped, my eyes pleading for more."

"Looking at you with compassionate eyes, I sit up on the table and call you to me."

"I eagerly follow you, wondering what is next . . ."

"You see me lay down on the table, raising my legs up so you have access to my hole. Please baby, fuck me. Give me all of your little boy's 5 inches."

"Yes, Hiti, I want to, that's all I want to do . . . fuck you . . ."

"I know baby, come here. Give me that hot cock of yours. I want to feel you inside me, and I want to tell you when to cum. I want us to cum together baby."

"Oh yeah, sounds so good . . . I slide my cock into you slowly, and it feels so hot."

"Yes, it does. My 'pussy' is so tight for you, wants to milk you dry. We start to fuck, I can feel your rod moving inside me, you can feel me tightening around you as we look at each other, my breasts flying with every movement."

"I stare into your eyes, transfixed, you're so beautiful and I feel like I'm about to cum . . ."

"Baby, you see my entire body. What do you notice?"

"I see your beautiful eyes and face, your long black hair, perfectly shaped breasts, slender stomach, long, slender legs. Such a hard body, I can't resist you."

"I know, it is a HARD body . . . you see something else though, too, don't you?"

"I thought you said we didn't have to talk about . . ."

"Come here baby, please, for me. Just take a look."

"I'm looking, as I fuck your ass and continue to pound you . . ."

"That's it baby. That's a good boy. I'll take care of you. Just look at it . . . it's so big, and it's for you baby."

"I don't know what to say . . ." I was really confused. She hadn't said it in words, but I knew what she was talking about. I stopped jacking myself off, but still breathed heavily and stayed hard . . . what on earth was happening? Why was she talking about it? And why did I actually still feel so hot? So confused . . .

"Lean in closer, baby. Are you leaning in? Can you do that for me?"

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