Jacking Off For Jenniferbycallmeishmael©
Jennifer and I work for the same law firm, but in different cities. She works in the same group I do and is basically my counterpart. She already worked for the firm when I was hired and spent two weeks with me when I started, to help get me up to speed. She comes into town about once a month for face-to-face meetings with clients and we speak on the phone every day. Let me get the basics out of the way so I can get into the story. Jennifer is 29 years old, with short, shoulder length brown-blonde hair. She's about 5"9", most of it legs. Her creamy white skin retains a soft supple look, even when she's tan. She's got great breasts but unfortunately hides them most of the time.
We've developed a great relationship because we talk on the phone 2-3 times a day. She's engaged to be married and I'm dating someone seriously. Although I thought she was attractive the first time I met her, I tried to keep that out of my mind because we'd be working so closely together. Recently though, I couldn't help myself and often found myself jacking-off and trying to imagine what she'd look like naked. Since I started doing that I also started to get better peeks at her legs and breasts when she was in the office. She often wears skirts and heels that make her legs look like they go to her shoulders. I've only got a cubicle at work so we often sit very close together when we're speaking face-to-face. It's these times I've caught long glances down her shirt.
When she'd come into town for a couple days at a time we'd often work late and then grab something to eat on the street below the building or in the restaurant in her hotel. Between dinners and talks on the phone we've discussed things more intimate than just shop talk. At one of these dinners she brought up, to my surprise, the fact that she'd been catching me taking longer than normal glances at her legs, ass and breasts. "I've started to notice, Steve, that you've become fascinated with my rack." Maybe it was the way she said it or that we'd had a couple drinks, but I didn't detect animosity or a rebuke in her tone.
"I'm sorry Jennifer" I fessed up, "Sometimes when it seems we're sitting on top of each other in my cube, I can't help it."
"Well, that's ok," she replied, "Just try not to be so obvious." With that the subject was over for the night.
She left town the next day and we continued to talk daily as we did normally. Two weeks later she was back in town. We were working late one night when out of nowhere she said, "Steve, I've been thinking about what we talked about the last time I was in town."
"About what?" I replied, a little confused.
"About you oogling my package," she replied lightheartedly.
"Hey, I've been better. I've forced myself not to do it the last few days."
"I know," she replied. "You've been very good." "I was actually going to admit to you," she continued, "that I caught myself doing the same to you when you started here. I've since forced myself to cut-it-out as well."
This caught me completely off-guard, and I didn't know what to say. Luckily, she continued. "Look, we're obviously attracted to each other, we've got a lot in common, and we've become great friends. Basically there's not much we can do about it. I'm getting married, you've got a girlfriend."
"I completely agree." I answered, still searching for a coherent thought.
"But I think there is something we can do and I might have solution," she offered. Neither one of us would do anything stupid nor impulsive to jeopardize our relationship nor the ones we've got at home. But we've got to do something to get this off our chests."
"Ok, I'm listening." I said with my heart in my throat.
She continued bluntly, "We can't screw. But what do you think about masturbating together? We wouldn't touch each other, but it might satisfy our curiosity. Not the most ethical of solutions, but maybe a practical one."
I thought about it for about two seconds – really I thought about her breasts, ass and legs. "I'm listening."
"Why don't we go back to my hotel room, get naked and get ourselves off? If we don't do it now, we may not have the courage to do it later."
I was already shutting my laptop down and asked her to lead the way.
"Oh, and since this is kind of a fantasy thing, give me a few minutes to change into something I think you'll like better. Meet me in my room in half-an-hour."
We took the elevator down together without a word. I turned into the bar around the corner for a quick beer and she walked two-blocks to her hotel.
Thirty minutes later I nervously knocked twice on her hotel room door. She quickly opened it and I understood what she meant by the fantasy reference. She was wearing an outfit she'd worn for a colleague's birthday party we both went to another time she was in town. My cock immediately began to stiffen. She had on a nearly see-through white cotton blouse, a short khaki skirt that I was sure was hiding a thong, and platform-like sandals, with a cork sole and heel. Her long creamy legs were bare and her newly painted pink nails were perched in the open toes of the sandals.
"Jesus, you look great. How'd you know?"
"How couldn't I?" She replied. "You were sneaking peeks all night the time I wore this."
She invited me in and sat down on a chair by a desk. I continued to stand. Regaining a little composure I asked how she wanted to do this.
"By the bulge in your pants," she responded, "I chose correctly. Now it's my turn. I want you out of those clothes and naked in the chair I'm sitting in. I'll get you a towel and some lotion if you need it. Be sure to pull the chair up to the edge of the bed," she continued over her shoulder as she walked to the bathroom.
Although visibly nervous, I decided I better do it if this was going to happen. I haphazardly threw my shoes off and piled my clothes in a corner behind the desk. For one second I had the terrifying feeling this was some kind of joke and ten people would come piling out of the bathroom.
Luckily that didn't happen. Jennifer returned 30 seconds later with a hand towel and a small bottle of hotel hand lotion. All of a sudden I became very aware that I was sitting there stark naked with my cock pointing straight up.
"Oh Steve, let me just look at you and that hard cock of yours." She stood there for about ten seconds looking me up and down as I fidgeted a bit but withstood her gaze.
"You ready beat-off boy?"
"Yeah, I'm ready." I breathlessly replied. Taking a little bit of control I asked her to walk over to my side of the bed.
"Ok, but be careful, we're keeping touching to a minimum." She warned.
"No problem," I replied, "I'm ready to get going with this fantasy. Take off the shirt and skirt, but keep your bra, panties and shoes."
"Alright," she responded, "it sounds like beat-off boy's ready to take control. (I'd already guessed that would be my nickname for tonight, I just hoped it wouldn't leave the room.)
I pushed away the ottoman in front of the chair and spread my legs so she could stand in front of me while she stripped. She turned around with her back to me, no more than six inches from my open legs, and began unbuttoning her blouse from the front. "Don't start without me." She said over her shoulder. I could see I was right about the thong under her skirt as she dropped her shirt to the floor. Then she turned around to reveal her milky white boobs pouring out of a white, low-cut satin bra. Her almond color nipples poked about the top. She reached around back and in a quick motion unzipped her skirt, let it fall to the ground and kicked it to the floor behind her. Looking up at her from the chair she looked six feet tall in her platform sandals and I found myself imaging her shapely legs wrapped around my shoulders.
"What do you think big boy? Everything you imagined?"
"Jennifer, you're beautiful," I replied.
"I'm glad you approve." She said as she rubbed both hands in between her legs. "My clit is already throbbing. Are you ready to start jacking that huge cock of yours? You can start and I'll get naked."
I began to slowly grip and stroke my throbbing cock. I knew if I went too fast this would be over before it began.
She walked around the side of the bed unhooked her bra and slid her panties to the floor. Her pubic hair was dark and shaved in a tight box around her pussy lips. She crawled on her hands and knees to the top of the bed, giving me a great view of her tight ass before she propped herself up on a couple pillows at the head of the bed. For a minute I imagined what it would be like to cup her small round ass cheeks in my hand.
I slid the chair to the foot of the bed and put my legs up on the mattress. She spread hers around mine with her sandals almost reaching the end.
"Pour some lotion on your cock so I can watch you slide your hand up and down the shaft." She ordered. "Oh yeah," she paused, "I want you to tell me what your fantasy is, and I'll tell you mine, but you can't cum until I tell you. Deal?"
"Deal." I responded.
With that she brought her right hand down to her cunt and began massaging with two fingers.
"Oh yeah, Steve, start beating your cock and tell me what you want me to do."
I was still stroking slowly so I wouldn't come and it didn't take me long to begin the fantasy I'd hashed out about ten times already.
"Tell me how you'd fuck me." I replied simply.
"That's easy enough," she responded working her fingers up and down on her clit. "You sure you can handle it?"
"Try me," I responded.
"First I'd get down on my hands and knees in front of you like you are now." "I'd lean in close and smother your cock in these perky C-cups. I'd move up and down, and up and down, until you leaked some pre-cum, like you're doing now. Then I'd take your huge cock in one hand and take the tip in between my lips."
She'd brought her knees up to her chest like she would if she was about to get fucked. I could see the bottom of her ass pressed tightly against the sheets on the bed. She now had her two fingers worked inside the folds of her pussy lips and was beginning to pant as she told her story.
"Then I'd start bobbing up and down while I cupped your balls. Would you grab my hair and guide my head while I was blowing you Steve?" She asked.
"Yeah," I grunted. "I'd grab the top of your head and guide you up and down my stiff cock."
"That's right beat-off boy, imagine me sucking you as your stroke your cock." She teased.
"When I felt your balls tighten, like you're about to blow a load in my mouth, I'd get up and tell you to get on your knees and eat me out. How'd you like to eat my pussy beat-off boy?"
"I'd lick you to you came." I responded.
"I know you would." She continued. "I'd stand above you and straddle your head while you fucked me with your tongue. Then I'd turn around and let you eat me from behind. Would you like to eat my pussy from behind? Would you work your tongue up my crack to my asshole? Oh, Steve my little asshole is so tight and I'd tell you to work your tongue in and out while you fingered my dripping cunt."
I was beating my cock faster now as I imagined giving Jennifer's beautiful ass a rim job. The only thing I wanted at that moment was to own that ass. "Okay," I interrupted, "tell me how you want me to enter you."
"Oh, you're ready to fuck me, huh?" Since I'm already standing, I'd tell you to get to your feet behind me. I'd brace myself with my hands on the bed and beg you to take me from behind. I can almost feel you standing behind me pounding my pussy. Oh yeah Steve, pound my pussy, grab my ass and stick your dick in as far as you can!"
She still had her knees in the air, her head was propped on a pile of pillows and her eyes were focused intently on my hand as I began to furiously pound my cock. She was working her fingers in and out of her pussy at a pretty good pace as well.
"You're doing a great job stroking your cock." she panted "Beat it hard, just like that."
"By now my knees would be week from you slamming my ass." She continued. "I'd get on my back on the bed and beg you to get on top and fill me with your big cock. Do you want me to wrap my legs around your shoulders? Oh, yeah, I can see you like that. Push my legs over my head! Grab my ankles and fuck the shit out of me! Oh yeah, like that, fuck me!" She seemed lost for a minute like she was about to cum. Then she stopped all of a sudden.
"Come over here." She ordered. I walked to the top of the bed. "Lay down where I am." She told me as she slid off the side. "We're going to touch but that's it, if you know what I mean."
I didn't exactly know what she meant but I'd comply to anything at this point. I sat up against the head board with my legs together and my cock still pointing at the ceiling.
"You can start stroking again." She allowed me. "But that's it."
With that she sat on the edge of the bed, swung a leg across me and straddled me above the knees with her ass pointing straight at my face.
"I want to you to look at my ass while you stroke your cock." She purred as my hand pumped within inches of her firm tiny ass. She brought her hand around and fingered herself from behind.
"Do you like looking at my ass? I bet you'd like to fuck it."
"Jennifer, your ass is gorgeous. I can't hold it much longer."
Then she swung around again so that she was sitting on my legs just below my cock.
"Make it last a little longer baby." Pretend I'm riding you with my pussy."
She knelt above me and continued to finger her cunt. Now she was drawing short breaths and her face was starting to flush. "Oh Steve, I want to cum so bad, are you ready to cum?"
"God yes, I'm ready." I replied.
"I want you to cum on me. Come over here and stroke your cock till it cums."
She sat on the edge of the bed and motioned me to stand in front of her. My dick was level with her beautiful tits. She grabbed my ass and pulled me closer so that my hand brushed her tits as I pumped my cock.
"Stroke your cock, faster! Faster! Can you see me fingering my cunt? Oh Steve I'm cumming, God I'm cumming!" She closed her eyes for a second as her orgasm overtook her.
That's all it took; two more quick strokes and cum shot from my dick.
"Oh Steve, cum on my tits. Cover my tits with your cum."
"Oh God, I'm still cumming." I yelled as my body convulsed and my knees weakened. I'd never brought myself to such a strong orgasm and my cum covered Jennifer's chest.
"Oh baby, that was great." She purred. Now you'll really have something to fantasize about next time you jack-off. I'm going to get cleaned up; I guess I'll see you at work tomorrow.
Figuring that was it, I gathered my clothes got dressed and left the room as I heard her start the shower. I can't say working with Jennifer is easier now, but if I had to do it over again I'd take her up on her offer every time.