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If you’ve been reading my previous stories you’ll know that in the late 1990’s I let the dark side of AOL get the better of me. One chat room in particular was especially influential on me. Anyway…
I was sitting chatting up a storm one evening when out of the blue an instant message popped up. It was from someone named Karen. She lived in Coronado not far from me. We chatted for a bit and eventually agreed to meet at a little bay side eatery the next day. She described herself as in her mid 30’s, 5 ft 7 in, medium build, short blonde hair. There should have been alarm bells going off but I figured there wasn’t any harm in meeting somewhere public. If she were a troll I’d just not see her again and if she was pleasant to both look at and be with we could be friends. At the time, sex was certainly not on my mind, I was married, content but not happily.
The next day came and I walked to the outside dining area on the boardwalk and looked about for the blue dress she said she’d be wearing. Her waving caught my eye and I was pleasantly surprised, she was not a troll. But then again neither was she stunningly attractive. She was, as close as I can put it, very ordinary. Karen was just as she described. Shoulder length straight blonde hair, a few inches shorter than I am, full figured (not meaning fat), measurements were 38-30-32, and she was in her early 30’s, pleasant to look at. She struck me as the kind of woman you would admire in line at the grocery store but not think about later.
She stood and gave me a brief hug and then we sat down to chat. Karen was divorced from a Navy pilot. I didn’t have to ask anything of this woman. She was opening her entire life to me. The best I could do was sit, eat, and listen.
The meeting went well and we planned to meet again. Over the next several months we saw each other a few times a week… we became very close plutonic non-sexual friends. Karen turned out to be a really odd bird when it came to openness and her life. She told me most everything she did, it was pretty clear she was damaged goods but we had a fun time. She liked light bondage, was a bit of a voyeur coupled with exhibitionist, and teased a lot, She had had breast enhancement surgery a few months before we met and she was still fighting with the doctor because she said he botched it. Eventually, I’d find out what that meant.
She was seeing a USMC Colonel and some guy who traveled the states inspecting theme park rides at the same time. I never asked but I’m pretty sure she was fucking them both but then again, her relationship with them could have been like ours was. She enjoyed telling me all about how she needed to decide which man she wanted to be with. I was married at the time and didn’t have a dog in the race.
We spent a lot of time together in my room at the BOQ. Again, nothing sexual just two good friends enjoying each other’s company. If she wound up spending the night, which was often, I’d sleep on the couch in the living room and she’d take the bed. Never did either of us express any interest in going any further.
We were spending the weekend together and it was Saturday night. We’d been at Coronado Beach most of the day and we’d come back, showered off the salt and sand and relaxed, lounging about in our pajamas. Yes, we wore pajamas when she stayed.
But tonight was a new situation. She was using my computer and chatting Antep Escort Bayan with her Theme Park guy online… but I was doing the typing and playfully suggesting things to say to him. She was sitting very close next to me, almost sharing the chair. Their conversation became more and more suggestive and erotic. Karen was clearly getting worked up over what he was saying.
After a while I glanced over at her and saw her nipples poking out behind her top. She was always braless at night so her nipples really showed. She saw me look, also glanced down, laughed and then quickly rubbed the palms of her hands over them. I assumed to calm them down but am not really sure anymore given what happened later.
Over the next 1/2 hour or so the chatting and laughing continued and her hands moved to her nipples more and more. I laughed at her and said we’d better stop. She said, “No,” scooted closer to me and took over the keyboard.
I sat down behind her and watched. Her neck was flushed and she kept rubbing her nipples and thighs. Just watching made me smile because it was so evident she was getting more and more horny, all this gave me a hard on and an evil thought.
I got onto my knees behind her and whispered, “Here, let me help you.” I began by rubbing her neck as she typed, I stayed on those a while before moving to her shoulders, where I again lingered. Her breathing had gotten deeper and more laboured, her nipples so hard I could even make out the puckered aerola around them. It seemed like the time to move.
I slipped my around up under the arms of the chair she was sitting in and duplicated what I’d seen her do. The palms of my hands lightly brushed over her nipples.
She kept typing and didn’t say anything or swat my hands away.
Soon I had a breast in each hand, I gently squeezed and kneaded them, occasionally tweaking her nipples between my thumb and forefinger as I kissed and licked the right side of her neck. It seemed they got even harder.
“Would you like more?” I teased. Karen’s only action was to quickly nod a few times as she typed.
I was already way beyond any comfort zone we’d established and was now reacting to my own arousal. Tits will do that to a guy.
My left hand stayed on her left breast while my right slowly began to descend. I stopped and stroked her belly for a bit. Karen had a nice firm body which reflected her working out daily. Something I didn’t do.
I pulled up on her top until her belly was exposed. My fingers traced her belly button once or twice and then slipped under her pajama bottoms. I felt her belly shudder and her shoulders shook under where I was lightly kissing. Her acceptance was given when she shifted a little and spread her legs as my finger tips touched hair, then the cleft which led to her clit.
Karen was very aroused. My fingers slipped over her clit and she bent forward a tiny bit in reaction. I felt that was going about far enough and let my fingers spread and slide around her clit. With her clit between my fingers I began a slow stroking.
Karen was typing furiously now and suddenly signed off.
I whispered to her, “Are you all done?”
Karen tipped her head to the left exposing her neck to me and nodded.
Being the devious little shit I am I pulled my hands from her pussy and breast and stood up saying, “Ok then, job done.”
“What the fuck was that?” Karen said when she turned to me. She had a huge grin on her face, game on.
“Well you seemed like you needed a hand, it must be hard rubbing your tits and clit and typing all at the same time,” I said and then smiled a huge cheesy grin, “I helped.”
Karen said, “Ya you helped alright. God that was exciting, we’ve never done that before.”
Innocently I said, “You never chat? Chatting is pretty common, I’m surprised.”
She turned her head and looked at me and said, “No stupid, we’ve never talked about sex this way. Shit I’m horny.” She pivoted 90 degrees to the right. The big old desk was an L-shaped one with the computer on the left side. The computer was now on her left.
She said, “Now leave me be” and tilted her head backward and closed her eyes, her legs extended under the desk.
“Oh you poor dear,” I said and massaged her neck, “Your nipples must be exhausted from being erect for that long, was it good for you?”
She reached up to cover her breasts and said “Oh shut up,” as she laughed.
“At bit frustrated are we? You need something absorbent or should I just get you a vibrator?” I asked.
She chuckled a little, “Mmmm, I could use one of those right now,” and her right hand rubbed her mound over her pajama bottoms.
I teased her, “Um, you might want to slip you hand under the pajamas. Take it from me, it’s better.”
I egged her on by leaning down and kissing the side of her neck again, saying softly, “Do you need a cock Karen? A nice hard hot fucking?”
Karen tilted her head to the left, turned it around to look at me and said, “You have an evil streak”… then she stuck her tongue out at me and rolled her chair a bit further under the desk. She moved her hands under it, jostled around a bit and a few moments later her pajama bottoms and panties flew at me.
She scrunched herself as far under the desk as the chair would allow, closed her eyes, leaned back and her hands disappeared under the desk again.
I picked the panties up and theatrically brought them to my nose. Her panties were wet in the crotch and had the muskiness of a woman. They smelled wonderful.
“Aw, that’s not fair,” I said sadly. Karen was too into pleasuring herself to pay much attention to me. I watched her for a moment, she was busy under the desk, her nipples nearly ripping through her pajama top. Every few seconds she’d utter a light, “ugh” or “ummm.” However, I was not to be denied a bit of lewdness myself.
“Ok, fair is fair, young lady,” I said “Since you aren’t going to allow me to see you I’m not going to allow you to see me,” and I retrieved my sleeping mask from the bedside. I had it for use during long flights. I slipped it over her eyes and dropped my pajamas and shorts off, tossing them into her lap.
Her hands came out from under the desk and felt them, “Bottoms and underwear, mmmmm,” she said. Then she dropped the pajamas on the floor but the underwear disappeared under the desk.
“Hey,” I said, “Those better come back clean and dry.”
There I stood with a hard cock and a masterbating woman at my desk trying to decide what to do next. I could jack off on her but that wasn’t very creative. Then I had it…
My own arousal probably weighed heavily on my odd decision. Karen was facing a mostly empty desk. I slid what few papers there were away and sat on it facing away from her, lifted my legs in the air so I didn’t hit her and then spun myself around so that I was facing her. Her hands were busy under the desk and I put my feet on the arms of her chair with my ass right at the edge of the desk.
In my mind it would be hilarious if she suddenly opened her eyes and found a cock and balls right in front of her. And yes, I was horny.
I hooked my ankles on the chair where the arms met the back and lay my legs open. My cock and balls were right at the edge of the desk.
I was sitting up but leaning back on my arms, “Ok you selfish woman you. Ready to share?”
Karen replied, “Oh God, what have you done now?”
Her left hand came up and felt my my leg. Her fingers were wet and sticky. She said, “Oh Jesus, you aren’t…”
I briefly let her feel my cock and balls to establish I was naked.
“Ok, what do you think you’re doing?” She asked.
Then I lifted her hand, licked her fingers and said, “No touching unless it’s mutual. We share like good little kiddies.”
Karen smiled behind her gritted teeth. Her breasts were heaving and would jiggle each time she came close to cuming. I sat up and started stroking, intending to cum on her pajama bottoms I had next to me.
She gasped out, “Are you almost there?”
“Ya” was all I could manage.
Karen surprised me by quickly unbuttoning her pajama top, pulling it open, and letting her tits spill out. Her hands went back under the desk but her breasts were in the open air. She leaned forward and I assisted her tits to encompass my cock. They were full and the aerolas and nipples puckered and engorged. I only managed a touches of my cock on them and I started to cum letting out a grunt as the orgasm hit me.
My spooge landed on her tits and she rubbed it around with her left hand, she pinched her left nipple hard, let out a “AHHH” and started to cum as well. She bent forward toward me and her head wound up on my right thigh, my cock next to her head. She turned her head and gently bit my thigh as I continued to stroke and milk my cock.
Her orgasm simmered for a long time. She leaned back into the chair and seemed to calm down but another wave would crash over her. I leaned back on my arms and took in the sight of her. Her breasts were nice but I could see what she was unhappy about. Her surgery scars were very clear.
Soon we both had calmed and she used my pajama bottoms to clean up her breasts.
We were back to being friends again… “You’re breasts are really quite lovely,” I said. She moved to cover them.
“They’re awful,” she said “I shouldn’t have shown you, but I love cum on them.”
I decided to change the subject, “So how do you intend to get to the shower without me seeing you naked?” I asked with a grin.
“You’re going to turn around like the gentleman you are.” she said.
“Ya, I was afraid of that,” I said and turned to the left away from her. I heard the door close and the shower come on. The shower and sink area were separate so I washed up and put on clean shorts and pajamas and went into the living room to wait.
Karen came out a while later stopped at the hallway and said, “Is this going to be a problem for us?”
I replied, “Is what going to be a problem?” She walked to me, kissed me on the cheek and said, “Thank you.”
There’s now a great distance between us, we remain good friends to this day and talk once a month or so. Nothing sexual ever happened again.
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