True story of my first time masturbating for a young woman on webcam
First of all, this is a TRUE story, so it won't have a bunch of unbelievable stuff happening, but hopefully you find it erotic anyway, I know I did.
I am recently divorced after 19 years. Bored, lonely, and yes, horny, I started looking around for online webcam sites to find some women who were maybe into getting off online, or possibly even just into watching guys masturbate, a fantasy I've always had.
It was tougher than I thought, most websites that claim to have 'hundreds of horny women' are actually just pay sites and the women on them professional models getting paid to get naked, and that didn't interest me.
Eventually I found a free site that, while not technically a 'porn' site, allowed adult webcam activities including nudity and masturbation.
From there it took even longer to find women who would even talk to you, many simply came to the site to actually CHAT with friends and were not interested in any sexual activity at all.
But I spent some time there, chatted up various women of various ages and got to know them and become friendly, and while I was always honest of my intentions of finding someone to 'play' with, they came to trust me enough to know I would not just whip my dick out on cam if that's not what they were into.
Eventually I found a few women that were fun, friendly and yes, DID like to play once in awhile, and enjoyed having guys watch them get naked.
One girl I met there was an 18 year old beauty named Jessie, and was just there to chat; she never got naked nor expressed any desire to see the men there jack off, she was just there for the social experience I guess.
We became friendly and chatted often, and again while she knew I was looking to meet some women to masturbate with, we never went there...we were simply friends who chatted and shared good times.
Then one day that changed.
You're probably wondering what she looked like by now, so I'll tell you: She was totally beautiful, thin, long blonde hair and stunning blue eyes...she was sexy, not in a slutty way but totally 'girl next door' type, and a perfect 18 year old body. She never got naked but one night she did take her shirt off and showed her bra and her breasts were perfect, round and firm like an 18 year olds should be.
Through our discussions, I found out several things about her: She was still living at home with mom and dad, was a senior in high school with plans to go to college right after, currently did not have a boyfriend...and she was still a virgin.
This kept me from pushing any kind of 'sex talk' with her too much; I knew she was inexperienced and I certainly did not want to scare her away or make her think I was some sicko pervert...Ok yeah I liked to masturbate and wanted to share that online but that's not THAT bad LOL. Plus...age difference aside, I really LIKED her and while I held no illusions about ever actually BEING with her, I considered her a friend at that point and respected her.
Anyway, one night there were several of us chatting away, and I was watching three ladies at once, when one of the more frisky ones started teasing and eventually getting naked...she was going to play for her crowd and I was getting in the mood to do some playing myself.
Jessie was online and on cam as well, and she was watching my cam too...at that point I was not doing anything sexual, just chatting with everyone.
Once the other girl started getting naked, and was allowing me to watch, I decided it would be best for me to private message Jessie to tell her what was up...she was not watching the other girl so had no clue.
I told Jessie that I was watching someone who was getting naked and that I decided I might have some 'personal fun' myself and that I wanted to warn her so she could log off my webcam.
To my utter surprise, Jessie wrote me back:
'Go ahead and have fun, I don't mind...I may stay on your cam, I may not, but thanks for letting me know.'
I was shocked; while we were friendly and had even done some harmless flirting and teasing, she had never once before expressed any kind of interest in seeing me naked, let alone masturbating.
Plus...reality check...I was a 40 something year old guy and she was a young, fresh 18 year old...she could watch ANY guy she wanted, much younger and much better looking than me, if that's what she was into.
Still...there she was, sitting in her bedroom, on her bed, looking as cute and sexy as ever even though she was totally dressed, and I KNEW she was watching ME, could see everything I was doing, and more importantly...what I was ABOUT to do!
So...I sat back, unzipped my jeans, and slid them down...even though I had initially decided to masturbate watching the OTHER girl, I found what was REALLY turning me on at that point was that Jessie was watching ME.
I took my time, and started by simply rubbing my already throbbing and fully erect cock through my underwear...I won't lie like most men do and claim some monster sized cock, but I have nothing to be ashamed of either, mine measures just under 7 inches.
as I slowly rubbed my cock, I found myself, not watching the other girl, who was already totally naked and shaking what she had to her audience, but instead watching Jessie's face to see her reactions, if any.
I kept waiting for the little beacon that told me Jessie was still watching my cam to go dark, which would tell me she logged off from my cam, but it didn;t happen...so I got bolder and finally pulled my cock free from my underwear.
I saw Jessie's eyes light up, and a smile slowly spread across her face...Oh my god, she was ENJOYING This!I couldn't believe it, a beautiful young girl was actually watching me masturbate for her! And LIKING it!
I smiled back, and took my throbbing cock in hand and started stroking, but slowly...I wanted to make this last as long as possible!
a PM popped up on my screen; it was Jessie:
I paused from my stroking long enough to type back:
'Thanks...you sure you're OK with this? I thought it might freak ou out.'
She wrote back 'no, I'm cool...keep going'
that was all the incentive I needed, and I once again began masturbating my cock, which was much harder than it usually gets when I just masturbate alone...now I had an audience, a beautiful sexy young 18 year old girl!
I struggled for control, I wanted to really give her a show, so I really took my time...varying strokes, pausing to play with my balls, or squeeze the head of my cock...all the while watching her face, seeing her eyes on me, and watching her body language.
I don't think she realized what she was doing but I could tell she was turned on...the way she would absently touch her hair, or squirm on her bed, and one time I almost thought her hand was going for her breasts until she caught herself and stopped it.
But it was her face that told the real story: she was totally enjoying watching me masturbate for her.
I got so caught up in playing with myself for her that I barely noticed when the other girl logged off her cam; I could care less about her now anyway, Jessie was the one I was masturbating to...and for.
after a bit, another PM from Jessie:
'you look like you're really enjoying that...gonna cum soon? I have to go soon and I wanna see'
That was all I needed!
I started stroking faster and felt the orgasm building, and it wasn't long before I was shooting stream after stream of cum all over my stomach and hand.
Jessie watched in utter fascination as I continued to stroke, squeezing every last drop of cum out of my still semi erect penis.
Finally I grabbed some tissues to clean my hands up, so I could write Jessie...I wanted to know what she was thinking.
Me: 'So...did you enjoy that? what did you think? I really wanna know'
Jessie: 'That was great...I've never seen a guy do that before, that was fun'
Me: 'really? You've never watched any other guys masturbate on cam here before???'
Jessie: 'nope, you're my first'
Me: 'wow, I'm honored then...what made you decide to stay and watch?'
Jessie: 'Because you're a nice guy and I like you and I was curious; I told you before I'm a virgin so I've never seen a guy naked before except some pictures, and I've never seen a guy masturbate or cum before until just now'
I was blown away...Ok it wasn't exactly taking her virginity BUT mine was the first real penis she had ever seen, and I was now one of her first real sexual experiences!
I wrote back: 'I am truly flattered then thank you! And I have to say it was a truly erotic experience for me, having you watch like that, so thank you for that too.'
Jessie: 'Really? wow, didn't think you would notice me that much since I wasn't naked at that other girl was.'
Me: 'That other girl logged off 10 minutes ago, I was aroused and excited from YOU'
even on webcam I could tell she was blushing at that point, but she smiled and wrote back:
'Cool, I'm glad then..maybe we can do it again sometime :)'
I assured her that I would love to, but only if it was something she was interested in. Then I had to ask:
'Jessie, I have to know...I know you watched out of curiosity, and that's cool, but...did you get aroused too?'
she took a few moments to write back, but when she did, she simply wrote...'yes'
I didn't want to make her uncomfortable, but I HAD to ask one more thing:
'Do you think you will masturbate later, thinking about this experience? about ME?'
Again a slight pause, then a smile on her face as she wrote back:
I decided to leave it alone at that.
We chatted for a bit more then she had to go, so we said our goodbyes.
We stayed in touch for a few months, and I masturbated for her on a few occasions more, and although she still would never get naked or masturbate along with me I found it highly erotic.
Eventually she graduated and went to college as she planned the next year and I sort of lost touch with her....but I often wonder if she still thinks of me, and if when she masturbates, memories of my cock float through her mind...