tagLetters & TranscriptsMy Best New Year's Eve Ever

My Best New Year's Eve Ever


wetpussy: I love you

I closed the chat window before replying. I was having no luck tonight. This was the third girl I had chatted with, but none of them had even managed to arouse me. All three said they had orgasmed, but I didn't know if it was true, and I really didn't care. I had not been having cybersex for very long, having only discovered a good chat site a couple of months ago, but I was a hell of a lot better at it than any of those three.

It was New Year's Eve, and I was home alone. My roommate was out with his girlfriend, and all my other friends were out with their significant others. I hated feeling like a third wheel, and not being in a relationship, I didn't feel like going to any parties with any of them. I also wasn't into the bar scene, so my only hope for a good time tonight was online.

It was still over an hour before midnight, and I had to admit I loved the idea of getting into a really good cyber session and starting out the new year with a mind-blowing orgasm. However, if my luck so far was any indication, I may as well load up some porn to jerk off to.

Not wanting to give up yet, and knowing that I've had some of the best self induced orgasms from cybering, I reentered the chat room. I had portrayed both men and women when having cybersex, and also of varying ages, but tonight I just wanted to be myself, a mid-20's male looking for a similar female. I was pretty sure one of the girls I had chatted with was in high school and lying about her age, judging by her grammar and use of language. Probably why she wasn't very arousing.

Thinking back on the other two, I realized that they all were trying to rush things. I wanted more than just the sex act, I wanted build up. Hell, I actually wanted to chat a bit. So instead of typing the usual teasing invitation suggesting cybersex, I wrote:

25m homealone: Any mid-20's women who are as bored and lonely as I am want to chat?

I looked at the words and realized how true they were. I hadn't been in a relationship for years. Not since I was in college. Hell, I still fantasized about Lisa. She was just under five foot in height, about a foot shorter than me, with shoulder length brown hair and deep brown eyes that I spent so much time looking into. Her breasts were on the small side, but that never bothered me, and part of me loved that I could engulf them easily in my hands. Her slight stature made it easy for me to lift her up, whether to tease her, to carry her around, or during sex. Those few times that I held her up against a wall and drove my hard cock into her again and again until we both shuddered in orgasm still ranked as my best sexual experiences.

Heh. I glanced down at my shorts, noticing the bulge in them that the three girls from before couldn't put there, but a minute of remembering my ex did. I wondered if that said something about them or me. I suddenly noticed that I had some responses to my inquiry in the chat room.

angellips23: Ill keep U company and U wont be bored ;)

I ignored it. First of all, I can't stand internet shorthand, but mostly I ignored her because she sounded just like the other three that night.

I skipped over a couple of others before seeing:

lonely 24f: Well, I think I fit those qualifications. What would you like to chat about?

Someone who sounded like they actually wanted to chat. Perfect.

25m homealone: Would you mind if we chatted in a private channel? The constantly moving text bothers me when I'm trying to talk with someone

I always liked going to a private room because it cut out distractions, and I liked to be alone with who I was chatting with. Admittedly, I was usually trying to cyber with a girl when I did that, and hoped to do it with this one, but at the moment I really just wanted a simple private chat.

lonely 24f: Sure. Give me the info

I breathed a small sigh of relief. I sent her a name and password and told her I'd see her there, then left the chat room. Creating the new room took no time at all, and I waited for her to show up. Instead of the '25m homealone' screen name, I used my actual name, 'Ben'.

A minute later, 'Amanda' entered the chat room. I was pleased to see she was using her real name, or at least a realistic one.

Ben: Hi there, Amanda

Ben: How are you?

Amanda: Like you, bored and lonely

I smiled and started to write a reply when:

Amanda: So why are you bored and lonely?

I deleted what I had written and thought for a moment.

Ben: I guess because I'm not in a relationship right now. Pretty much everyone I know is out with a spouse or date tonight, so that's the lonely part

I thought some more.

Ben: As for the bored...I know I could go out to a bar or club and be surrounded by a bunch of people, but that really just doesn't interest me

Before she could respond, I typed out:

Ben: How about you?

Amanda: Similar reasons. I could have had a date tonight and gone out to a party, but I didn't know the guy, it was something a friend was setting up for me. I figured I'd rather stay home

Ben: Any particular reason?

A moment passed before she typed:

Amanda: I broke up with my long term boyfriend a few months ago, and I guess that I don't feel like jumping into another relationship with some guy I don't know at all. It'd feel weird. And New Year's of all nights? Nope, don't need that

Ben: How long were you together?

Amanda: Three years

Amanda: Why doesn't the bar scene interest you?

Ben: Well, I guess the whole goal of going out clubbing or anything like that is to get drunk, and try to get laid. I'm not a huge drinker and one-night stands aren't my thing

I thought to myself how funny it was that I didn't want to have a casual physical encounter with a woman, but online, that was all I wanted. I'd typically chat with a girl, get her off, get myself off, and then never find her online again. A couple of times that was a bad thing, as I'd had such a wonderful experience with them that I would have loved to cyber with them again. But that way at least, things didn't get messy with talk of meeting for real, or some kind of online relationship that would probably be doomed to failure.

Amanda: Yeah, that's kind of how I've always felt about bars and stuff

I thought about where I wanted this conversation to go, but before I got far, she continued.

Amanda: So who are you, Ben? What do you do, what do you like, etc?

Ben: I'm me, of course! :)

I was stalling a little as I thought what I wanted to say. This would be my chance to lie and try to impress her, but I didn't feel like coming up with some fancy story, so I just told the truth.

Ben: I'm 25 years old, majored in Computer Science in college and managed to get a good job right after graduating

Ben: I enjoy hanging out with my friends, at least normally. Obviously not tonight :)

Amanda: :)

Ben: I also like to read fiction novels, work on computer programs, which is probably why I'm good at my job, and watch movies

Ben: I also like to hike in the woods, which are easy to find around here

Amanda: Here too

Amanda: So would you like to know about me?

I smiled to myself.

Ben: I was just about to ask. And yes, I would

Amanda: I'm Amanda, a 24 year old engineer. Or I was, I recently lost my job

Ben: I'm sorry

This was a crappy time to be unemployed.

Amanda: Thanks. But anyway, I like working with my hands, fiddling with things

I wondered for a second if she realized that what she wrote could be taken the wrong way. Or maybe that's what she had intended. Amanda continued before I could dwell on it more.

Amanda: I like working on cars, which is probably a bit unusual for a girl, but whatever

Amanda: I also like video games and sci-fi/fantasy novels

Amanda: I'm a geek, I guess :)

Ben: Part of me wonders if you're just making this up trying to impress me. I thought girls like you were imaginary :P

Amanda: Haha, well I'm very real

Ben: So what did you do as an engineer?

Amanda: I primarily worked with the other side of your field. I worked on microchips and circuit boards for computers and other electrical equipment.

I nodded to myself.

Ben: I guess with the current economy that field is taking a bit of a downturn. They just closed a plant near me recently that developed older computer components. They're remodeling it for the production of newer equipment

Amanda was silent for a minute, then typed:

Amanda: I'm beginning to think we live in the same city, because that's exactly what happened to my work

Ben: Then this would be the first time that I've ever lived remotely near anyone I've chatted with, not counting my friends

I was enjoying this chat. It was somehow nice to share my woes with someone with similar problems, even though it sounded like she was worse off than me.

Ben: So, what are you going to do now that you're out of work?

Amanda: *sigh* Find something else. I live on my own in a two bedroom apartment, so I really need income or I'm not going to be able to afford my rent soon

Amanda: I got a nice severance package when I was laid off, but it won't last forever, you know?

Part of her response intrigued me.

Ben: Why do you have a 2 bedroom? Got a lot of stuff?

Amanda: Of course!

Amanda: I told you I like to work with my hands. The other room is like my workshop.

Ben: That's cool!

And it was. I wished I had an extra room for my hobbies.

Amanda: Yeah, I suppose. Although it's pointless at the moment, since I can't afford to indulge in new stuff to work on, and the extra room costs me more each month than a one bedroom would.

Ben: You sound a bit stressed

Amanda: Yeah I am

A moment passed and she continued:

Amanda: To tell the truth, that's kind of why I'm online tonight.

I eyebrows shot up. Was she saying what I thought she was saying?

Ben: Are you looking for a bit of fun?

Amanda: Isn't everyone who goes into that chatroom? :)

Amanda: Besides, you passed a test

Ben: What test?

Amanda: Well you were actually willing to chat for a bit and not try to rush things, which means you will probably take your time if our chat turns to...other things ;)

Ben: May I ask what you look like and what you are wearing?

Amanda: You can ask

I waited, but she didn't type anything. I smiled as I caught on.

Ben: So, what do you look like and what are you wearing?

Ben: Tease :)

Amanda: Well, I'm 5'2", with a slight body frame, short brown hair, and brown eyes

Amanda: I'm nearsighted so I do wear some thick glasses, which I think turn some people off

I found it interesting that she included that if she thought it turned guys off.

Amanda: As for what I'm wearing, just some pajama pants and a cami

I also noted that she didn't mention a breast size, which made me think they were somewhat small and she didn't want to mention that. Maybe the glasses comment was to distract me from that. Didn't matter to me. I let it go without comment.

Amanda: How about you?

Ben: Well, I'm just a bit over 6 foot, about 190 lbs, black hair and green eyes

Amanda: Oooh, I love a guy with green eyes.

Ben: Thanks. And just for the record, I think glasses are sexy

Ben: I am wearing a t-shirt and sweatshorts.

Amanda: What, no underwear?

I could just imagine a teasing smile on this woman's face.

Ben: Well, yeah, a pair of briefs too. You didn't mention any underwear.

Amanda: No, I didn't, did I? ;)

My eyebrows shot up. I felt a slight bulge in my shorts and glanced down at my crotch to see my cock straining against the fabric containing it. I had gotten aroused without even realizing it.

Ben: Well, since you're so stressed, would you like it if I rubbed your neck and shoulders?

I started falling into my usual seduction routine with ease. However it seemed that she was no stranger to cybersex herself.

Amanda: Only if you'll like it when I moan and purr at the touch of your hands

She certainly knew how to get a guy going, as the tent in my shorts grew a little larger.

Ben: Are you sitting in a chair or lying in bed?

I know that sounds weird, but I feel that it helps a person get into the fantasy more if you keep things real. If I told a girl that I sucked her bare nipple into my mouth, but she was wearing a shirt, that would distance her a little from the fantasy. If I instead mention how I pull her shirt up to reveal her hard nipple which I then suck between my lips, it gives her the opportunity to raise her shirt and let her hand play the part of my mouth. Same thing here. I don't want to say I straddle her back and rub her shoulders if she's in a chair. Which turned out to be the case.

Amanda: I'm in a chair

Amanda: And I pull the straps of my cami over my shoulders to give your hands free access

Awesome. She seemed to cyber the same way I did, with lots of little details. The more details, the better the fantasy, and therefore the better the sex.

Ben: I stand behind you and gently begin to massage your shoulders

Ben: Your skin feels so soft under my hands

Ben: I move one hand to the nape of your neck

Ben: I squeeze gently, doing my best to work out some of the tension in it.

Amanda: Mmm, that feels so nice

Ben: I lean over so I can whisper, 'I'm glad' in your ear as my hands continue their work

Amanda: You feel me shiver slightly as your breath tickles my ear

I smiled. She was good. I really wanted to start touching myself, or at least pull my now incredibly hard cock out of my shorts to get more comfortable, but I never start taking off my clothes until it happens in the fantasy.

Ben: I smile at you, enjoying both your reaction and the feel of your skin beneath my hands

Ben: Bent over like this, I catch the scent of your hair and it smells wonderful

Ben: I start really kneading your shoulders, giving your muscles a deep massage

Amanda: Oooh, it almost hurts, but it's sooo good

Amanda: I push back against your hands, loving the warmth of them as they drain the aches from my body

Ben: My hands move down to caress your upper arms

Ben: Running up and down, over the straps of your cami, from the shoulder to the elbow and back

Amanda: You're making the hairs of my neck stand on end

I smiled as an idea came to me.

Ben: You must be cold. I lean down and breathe warm air on your neck to heat you up

I liked writing lines that could be taken more than one way.

Amanda: Now they're even more on end, and I sigh as I bask in the pleasure of your hands caressing me and your hot breath on my neck

Amanda: I can't help but reach back and run my fingers through your hair

Amanda: Grasping it in my hand to pull you forward

Ben: I let you, moving my head with your hand. My hands never stopping

Amanda: I tilt my head back and pull your lips to mine, kissing you deeply

I was so worked up right now, and from nothing but describing a massage and a hint of a kiss.

Ben: I return your kiss, letting my tongue barely touch your lips. Tasting you

Amanda: My tongue goes out to meet yours, giving it the slightest touch before retreating back to my mouth

Ben: I moan softly at the touch of your tongue to mine

Amanda: I push your head back a little bit, my fingers still entwined in your hair

Amanda: Come around in front of me

Ben: My hands leave your arms as I move around the chair to stand in front of you

Ben: I look down at your beautiful face, unable to stop myself from smiling at the kiss we just shared

Amanda: I believe you were wearing sweatshorts

Amanda: Anything odd about them right now?

I chuckled.

Ben: If you mean the large bulge inside them, then yes, I suppose there might be

Again, I could imagine a playful, even flirty smile on her face.

Amanda: Aw, someone should probably do something about that

Amanda: I slide my fingers into the waistband of your shorts and briefs and pull down

Amanda: Are you shaved?

Ben: No

Amanda: My fingers brush against your pubic hair as I pull your shorts down and over the bulge in them

Ben: My cock springs out when you pull my shorts down, pointing straight at you

I slid my shorts and underwear down, groaning a little in relief as my cock sprang out, free from constraint at last.

Amanda: I slide your shorts all the way down to the floor, using my feet when my arms won't reach far enough

Amanda: My eyes lock onto your cock, so hard, right in front of my face

Amanda: You can feel my quickened breathing on it, my face is so close

Ben: I feel somewhat silly standing here in just a shirt, so I grab the bottom of it and pull it up and off

I matched action to my words.

Ben: I toss it aside, kicking my shorts and underwear off to land next to it

Ben: I moan as I feel your warm breath on my cock. Arousing me further

Amanda: How long are you?

I was seven and a half inches, but I rounded up.

Ben: 8 inches, medium thickness I think

Ben: I haven't really compared myself with anyone :)

Amanda: :)

Amanda: Your massage felt so good, it's really only fair if I were to give you a massage in return

She waited a moment for a response, but I just let her continue.

Amanda: I reach out and grasp your dick in my left hand, and I start to stroke you gently

Amanda: I look up at your face to see your reaction

Ben: My eyes are fixed at the sight of your hand stroking me, my mouth hanging open

Ben: When I realize you are looking up at me, I gaze deep into your beautiful brown eyes, smiling broadly

My typing slowed down a little as I rubbed my cock with my left hand, imagining it was hers.

Ben: You really are good with your hands

Amanda: Hehe, I've barely even started, but I'll take that compliment

Amanda: However, I think I should show you how good I am with my mouth

I stroked myself a little harder at her words.

Amanda: I lean forward and touch my tongue to your hard dick, running it around the head

Amanda: I change my grip on you so that I'm stroking the base, my small hands leaving a good amount of your cock uncovered

Ben: I moan at the sensations your hand and tongue send through my body

I moved my hand to match what she said.

Amanda: I smile at your moan, still looking into your eyes, and suck your head into my mouth

Amanda: You can feel my tongue still running around it

Amanda: Tickling the underside

Amanda: Running through your small slit

I moaned for real as my right hand started to caress the head of my cock, and I could feel it when I started smearing pre-cum all over. I wiped my hand on my leg before moving it back to the keyboard.

Ben: God, that feels so good

Ben: My hands go to either side of your head, running through your hair and caressing your cheeks

Ben: You can taste the pre-cum that has leaked out

Amanda: I slide more of you inside my mouth, letting my tongue focus on the underside as I begin to move back and forth

Amanda: My hand matches the motion of my mouth on your dick

Amanda: Still looking into your eyes

Amanda: I let out a moan as I taste you

God, I was going to lose it. But I didn't want things to end yet. I mean, sure, I'd make sure she got a turn, but at that point, things would be over and I'd probably be ready to go again. That's why I liked to get the girl off first, and then get off myself. I had to take back control.

Ben: My hands tighten on your head, and you feel me pull away, pulling my cock from your mouth

Amanda: What's wrong?

I stopped rubbing myself, noticing how I was oozing pre-cum and watched as a drop ran down the head and part of my shaft.

Ben: You're a little too good :)

Ben: I want to pleasure you for a bit now

Ben: I kneel down so that we're eye to eye

Amanda: Mmm, no objection

Amanda: I look longingly at your dick, a tasty morsel getting away from me, but look back at your eyes when you kneel

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