Masturbating Colleagues

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I've worked with Becky for 11+ years, and over that time our friendship has evolved in curious and interesting ways. Some background: Becky is 48 years old and single. Her husband was killed tragically about 9 years ago in a skiing accident and she has raised two children on her own and they are now off at college. I am 42, married with 1 child with a very boring sex life (actually it is almost non-existent). I guess the best way to describe Becky would be as an average middle-age woman. She is about 5'6', approximately 140 lbs, shortish auburn hair (with streaks of gray showing) and stunning green eyes and a great smile. She has wide hips and a somewhat ample derriere, and average sized breasts. Becky is a VERY sweet and caring woman, and she is always helping other people out in the office.

About 3 years after her husband passed away our office friendship began to strengthen, although it was strictly that - an office friendship. We would occasionally have lunch in the cafeteria together and would talk on breaks, etc. Over the years we became more and more comfortable sharing more personal details about our lives, and over the last year I revealed to her that I was unsatisfied with my sex life. I didn't come out and say it blatantly, it just became known through our kidding and needling that I wasn't getting much, and neither was she. It wasn't like we would talk about sex overtly, but it did come up in round about ways. One particular day we took a long lunch (a rarity) and actually went to a local restaurant to eat. Our conversation turned to what we had done the night before, and I told her 'the usual'. She wanted to know what 'the usual' was. Feeling a bit bold I told her my wife and I had dinner, I checked my email and then watched the news. When my wife fell asleep on the couch I retired downstairs to surf the Internet and take care of business. She looked at me quizzically for several seconds, and then said,'OHHHH, you took care of BUSINESS' and she started to blush and laugh.'I know what you mean, Chris. I get it now. I took care of business last night, too.' She was blushing a deep shade of red. This sweet middle aged Mom was confessing to me that she had pleasured herself the previous night.

I took the opportunity to press forward with our somewhat racy and risqué conversation.'You did, huh? You're naughty' I said to her and smiled.'You're lucky you can do it alone without having to worry about someone walking in on you. I have to do it on the snide and hope my wife or daughter doesn't catch me.'

'I know, I know. Now that my kids are away I miss them SO much, but I also do enjoy the privacy part of it. . I can decorate the house any way I want, garden when I feel like it, or watch any movie I want. Actually last night I watched one of those adult movies on Cinemax. I never would have done that if the kids were in the house.'

I replied,'It must have been a great movie if you ended up 'taking care of business''.

'It definitely was,' she said softly. There was a twinkle in her eye before she shyly looked down at her food.

My groin was beginning to stir slightly as our conversation progressed. I have NEVER thought of Becky in a sexual way before, not even in my fantasies, but sitting here talking to her about masturbation was getting my mind in gear.

'You know, sometimes when I do it, I think about watching someone else doing the same thing, or having them watch me', I said to her.'I think that is such a turn-on.'

She looked up from her pasta.'Really? Oh my god, sometimes I think about that too. Actually I think about it a lot.' She was still blushing, but appeared to be much more willing to continue on this subject now that we found we had something in common.

I told her,'Last night I actually fantasized about my sister in law walking downstairs and catching me doing it while I was looking at porn on the Internet. Then she ends up, you know, taking off her clothes and joining me.'

Becky said,'You have to promise not to tell ANYONE this, OK? I don't want anyone at work to think I'm a slut or anything, but I think about having a repairman come into my bathroom and catch me doing it in the shower. And then he does things to me with his mouth and hands...' She paused.'I better stop there or I'll get in trouble'. She was blushing heavily, and I was looking at her in a completely different way now. She had on a plain white blouse and black slacks; far from sexy, yet I found myself wondering what it would be like to see her in her bra, and what kind of panties she wore...

I asked Becky how long it had been since she had dated a man (although I knew the answer).'It's been about 2 years since I went out with Ned. I'm really just not interested. I don't want to get all hung up in a relationship, but the thing I do miss of course is the ... intimacy,' she confided.

'I have an idea' I told her. And I did. And I was hoping she wouldn't freak out.

'Well, you know that my sex life sucks. And it's been a long time since you've been with a guy. Why don't we pick a night and I can come over and we can (I was VERY nervous here, and I could tell by the look in her eyes she was too), you know, have fun.'

'But Chris, you're married. I don't want you put your marriage in jeopardy. It wouldn't be fair.'

'How about this,' I said.'We promise each other that it will be just the one time, and there will be no, um, intercourse. OK?'

She looked at me with a whole range of emotions showing through her eyes. Confusion. Desire. Longing. Mistrust. I could see it all.

Finally she said,'But how are you going to get out for a night? What will you tell your wife'?

'Not a problem' I told her.'She and my daughter are going to her sisters in Pennsylvania this weekend and I'll be on my own. No need to make an excuse.'

'Well, I guess... I don't know, Chris. I really would like too, but...'

'No buts' I said.'Let's plan on this Friday night.'. I usually am not overly assertive, but in this case I had extra incentive. SEX!

So our plans were made. We picked a time, and she gave me directions to her house (about 30 miles from where I live) We quickly finished lunch and headed back to work (it was a Wednesday afternoon). The next 2 days were ones of anticipation, and I made sure I broke out of my nightly routine of masturbating so I would be primed for my night with Becky. I also made a stop on the way home Thursday at a local Adult Gift Store and purchased a small ('pocket rocket') vibrator. I wasn't sure if Becky had one (I guessed that she didn't knowing her shy and sweet demeanor - I couldn't see her walking into an adult shop or even ordering one through the mail). I hid it deep in my trunk along with a pack of new batteries, a fragrant candle I picked up, and 2 videos I had purchased several years before for my wife and I. They were 'instructional videos' for couples that featured real-life men and women in a variety of sexual situations. It was presented as educational, and had some spliced-in interviews of a therapist talking to these couples, but it was also VERY arousing watching regular people have sex. My wife thought they were porno and they ended up in the back of my closet gathering dust.

Friday evening finally arrived (I had confirmed with Becky that afternoon we were still on - and she blushed AGAIN when she said yes, she was looking forward to it). At 4:30 I called my wife and found she was on her way out the door to her sister's. I left the office, stopped to get some refreshments, and was at Becky's house 40 minutes later. She answered the door and invited me in. She was still dressed in her work clothes; a black short sleeve sweater blouse and black & white plaid slacks. Her shoes were off and I noticed she was either wearing stockings or pantyhose.

She gave me a quick peck on the cheek and asked me how I was. I told her that, honestly, I was both nervous and very excited. She told me that she felt the same way, and I suggested that a few refreshments were in order. Becky then gave me a tour of the house, including the upstairs (where her bedroom was), downstairs (where her computer and living rooms were) and the den. As I was pouring us some soda, the doorbell rang and I was startled momentarily until she laughingly told me to relax, it was just the pizza she ordered. As we sat down on her living room floor enjoying the pizza we were both 100% more comfortable than even 30 minutes before. After I finished my second slice I went to the kitchen to retrieve the bag I bought my goodies in. I sat down next to Becky and placed the candle on the coffee table and lit it. It was Lilac, and she loved it.

I showed her the videos, and she intently studied the jackets. I told her that I had enjoyed watching them in the past and found them very erotic, and she said,'If you like them, I definitely want to watch them!' She had a glow about her - I believed she was starting to get aroused.

Finally I took out the vibrator and pack of batteries. I said,'I hope you're not offended, but I thought you might enjoy this. I don't know if you already have one, but if you do now you have a spare.'

'Oh CHRIS!' she shouted.'Oh my god, I always wanted one of these but I was always too embarrassed to get one. You are the BEST.' She threw her arms around me and hugged me, and for the first time I felt her breasts pressed against me. As she eased back, I lean forward and kissed her, gently at first, and then more passionately until we were both French kissing like teenagers. After about 30 seconds Becky backed off and said,'I'm going to get changed, OK? I'll be back in just a minute'.

I took the opportunity to 1) turn on the TV and VCR and slip in one of the tapes, and 2) to put the batteries into the vibrator. When Becky returned a few minutes later she looked terrific, again not a sex goddess but what she was wearing caused me to become almost fully aroused. She had changed into nothing but a large, oversized man's white dress shirt that stopped at mid thigh. I guessed she still had panties on, and could see through the thin material of her shirt that she was wearing a bra. The top 3 buttons of the shirt were undone, revealing a hint of cleavage. Her breasts actually appeared bigger than I had ever noticed up until then (probably because of the conservative outfits she wore to work. ).

Becky sat right next to me on the couch. I told her I had put the video in and she grabbed the remote control from the coffee table and hit play. Now, as 'the man' I'm used to having the remote, but she very adeptly fast forwarded through the initial credits and prologue and 'counselor session' to a scene of a couple (obviously married) on a blanket on the floor of a living room in Anywhere, USA. They were both naked, and the man was lying on his back. They were middle aged, the woman had big breasts and was slim, the man rotund and slightly bald (much like me) and his penis hung limply to the side. The woman proceeded to squirt baby oil on her hands and began to give him a hand job. As the scene unfolded, Becky said that she hadn't seen a dirty movie in many years, but did like reading erotic stories sometimes to get her 'in the mood'. I said we could turn it off, and she immediately said,'Don't you DARE!' and broke down laughing. She turned to me and said,'Well, I got out of my work clothes and got comfortable, aren't you going to?'. The shy, reserved and sweet woman I knew, and was attracted to, was beginning to show her sexy, naughty side - and I loved it.

Without making too much of a show of it (I remained seated), I slipped off my shoes and socks, then unbuttoned and removed my shirt. As I unbuckled my pants and began to ease them down, Becky kept glancing back and forth between me and the scene in the video, where the wife was on her knees expertly stroking her husband while his hands wandered over her breasts and rear. I was soon sitting in nothing but my red and green plaid boxers, sporting an obvious erection. Becky saw it, smiled and said to me,'You must really like this movie'. I told her I did, but it wasn't the only reason I was excited. I asked her if she could unbutton her shirt. With my request, she became flustered and began to blush once again.

'You don't want to see my old lady body, do you? I mean, come-on. I'm not even close to that woman (she pointed at the screen) and I'm fat. I would rather just keep my clothes on, OK?'

I assured her that she was beautiful, she wasn't fat, and reminded her that the reason for my arousal was seeing her already half-undressed. I also told her it would be difficult to have any 'fun' with our clothes on.

'Come on, relax Beck,' I told her.'It's fine. It's just you and me. You're a beautiful gal. Don't be bashful. What goes on here will stay here. I have an idea. Let's start by just unbuttoning your blouse (I reached over and unbuttoned her top most button...) and we'll see what happens from there, OK?' As I touched her, she became rigid. I leaned forward and kissed her cheek, then her neck, and the tenseness seemed to ooze out of her. I sat back and asked her to unbutton it the rest of the way.

'It's part of what I have been fantasizing about, Beck. Seeing you take off your clothes, imagining what you would look like, and seeing you touch yourself.'

She smiled at me; still blushing of course, and slowly unbuttoned her shirt the rest of the way. I noticed that her blushing wasn't limited to just her face. The top of her chest was red as well, and as she opened her shirt I saw the sight I had longed to see: she had on an under wire, white lacy bra and her nipples were clearly erect as they poked out the material. Her panties were, well, what I had expected. White briefs (Hanes I later discovered) than came up to just below her belly button. No sexy g-string...but they were incredibly sexy to me.

Her breathing was a bit shallow. I handed her a soda and she took another long sip and handed it back to me, and as I placed it on the table behind the couch, I grabbed the vibrator and turned it on low. The whirring sound made Becky jump a bit, and she saw me with it and smiled. I handed it to her and said,'Here, have some fun'. As she took it I sat back, our legs touching, and began to slowly fondle myself through my boxers. Becky's eyes fixed on my hand and she looked at me and smiled.'Feel good?' she asked.

'You bet! Go ahead, try out your new toy.'

She tentatively placed the vibrator down between her legs. They were only slightly spread apart, most likely because she was still somewhat nervous. She bought the tip of the 4' silver pocket rocket up against the crotch of her panties and let out a small 'yelp' and her back arched momentarily. She immediately pulled it away and started to giggle like a schoolgirl.

'Oh my god, that feels unbelievable. It's only going to take me about 10 seconds to come.' As she said that she looked at me and bit her lower lip in embarrassment, as if using the word 'come' was a mortal sin.

'I'll time you,' I joked.'Go for it'. She once again placed the vibrator between her legs, and this time she spread them a bit further apart. She gently slid it up and down her crotch, and her eyes fluttered open and closed. Her breathing became noticeably heavier, and she let out a series of soft sighs. As she did so, I worked my erection out of the opening of my boxers to see the light of day, and when she finally realized I was exposed, she gave me a wicked smile filled with fun and lust. No words were spoken as she locked her eyes onto my hard penis, which was quite wet and slick with pre-cum (I leak A LOT when I get excited and haven't masturbated for a few days - which isn't often hahaha). I slowly began stroking, wanting to see Becky get off. It didn't take long. She began sliding her toy more and more rapidly up the crotch of her underwear, which now contained several spots of wetness. She lifted her hips up off of the couch, let out a long 'Ohhhhhhhhhhhhhh mmmmmmmmmmmm' and ground the tip of the vibrator into the area of her clit. Her right hand went to her breast and squeezed it tight. Her rapid panting and sighing soon diminished, and she looked at me and said,'That's the best orgasm I've had in a LONG time', and she started giggling again.

'I'm glad Becky. That was SOOOO sexy. I've always wanted to watch a woman do that.' I was still massaging and stroking my erection (slightly above average size, by the way. 7' cut, with a thick head. When erect it bends up towards my naval).

'Now it's your turn,' she said. I didn't hesitate as I completely stripped off my boxers and lay back on the couch naked, my feet barely touching the floor. I asked Becky to fast forward to the next scene, and she found a couple in their bedroom, this time a chunky older woman (50ish) was sitting naked on the foot of their bed and her slight, short husband was standing naked in front of her. She proceeded to fellate him, and then placed his long skinny penis between her breasts as he titty-screwed her. That had always been a favorite fantasy of mine, and I began to stroke a bit more in earnest. As I did, Becky was completely relaxed, asking me if this was how I always masturbated, how long it normally took me to ejaculate, did I ejaculate more than once a day, etc. She was very chatty and full of questions suddenly. Since she was so relaxed I saw an opening and asked her to take off her bra. Surprisingly she did so without any resistance. She reached around and unclasped it and let it fall forward, then down to the floor. I HAD underestimated her. Her breasts were at least 36B and were capped by very large (actually the largest I had ever seen, in pictures or in person) pink areolas. Her nipples remained erect, the areolas capped by points that looked exactly like pencil eraser tips. While her breasts were full, they did sag a bit, but were still impressive for a woman her age. She asked if I like them.

'I LOVE them,' I told her.'Since I'm naked, and you still have on your underpants, don't you think it would be fairer if you took them off?' I asked her with a mischievous and hopeful smile.

'I don't know, Chris. I, well, I'm just embarrassed. You really don't want to see...'

'Becky, don't tell me what I do and don't want to see. You are gorgeous, and have nothing to be ashamed of. You are incredibly sexy to me. Go on, it's fine.'

She looked at me, hesitated momentarily and then hooked her thumbs into the waistband of her panties. In one quick motion they were around her ankles, and then off. We were sitting side-by-side, legs pressed against each other, naked. Becky's hands were in her lap, hiding her treasure. I continued to masturbate, and then turned sideways so my erection pressed against her thigh. The feeling was electric. I started to hump her leg slowly and deliberately and as I did so I reached over with my right hand and began to squeeze her left breast. I drew lazy circles around her nipple with my forefinger and occasionally gave it a light tweak. I leaned forward and whispered in her ear,'Let me see you masturbate again, Becky. We can do it together and come at the same time. I want to come SO bad for you.' She sighed lustily and nodded her head yes. I sat back and as I did her legs eased up until they were spread open. For the first time I saw her vagina. It was covered with a light layer of brown pubic hair, very straight (not curly or thick) and soft looking. Her lips were visibly engorged with blood and still slightly opened from her masturbation from about 10 minutes before. Some of the hair around her cleft was matted with moisture. Her belly was that of a middle age woman who had 2 kids, but she was by no means fat. The entire sight - her reclining back on the couch with her beautiful breasts and erect nipples on display, her naked torso and exposed vagina, her legs slightly splayed open - was one I will never forget.

I took the initiative and stood in directly front of her, and began to masturbate. She too placed her left hand down between her legs (she was a righty in everything else, but masturbated lefty, just like me!) and did the same. No vibrator this time (she explained to me later she was so used to using her hand that she forgot about it!). Her middle finger worked it's way up and down her slit, and in moments she was masturbating like a wild woman for me: working her breasts and nipples, her lips open full, her vagina wet and slick and her middle finger circling, pinching and flicking her clit and occasionally inserting it deep inside. It was more than I could take, and I announced that I was going to come. As I took a step forward between her open legs (thinking about fulfilling my fantasy of coming on a woman's face and breasts, like in a porno...) Becky also sat forward, as if reading my mind. Her moans and sounds of ecstasy were MUCH louder than when she had gotten off the first time (I guess it had been a warm up act...) and she began to talk dirty to me.'Yes, stroke you big hard dick. Shoot your come all over my tits.' Now, having a woman as I've described (sweet, motherly, conservative) talk to me that way while we were masturbating together sent me over the edge. I began to come: the first few pulses produced some 'minor flooding' that leaked over my hand and onto the floor. But the main eruption was the best orgasm I ever experienced, and the messiest. The first stream of come shot out so hard it flew over Becky's shoulder and hit the back of the couch. The next splattered against her left cheek (some in her hair) and down her left arm. I adjusted and unloaded 4-5 more heavy streams of come all over her neck and breasts. (This event was for me similar to what happens to some people when they are in a car accident: I remember ever detail vividly and it was almost as if time stood still...) As my orgasm was concluding (it lasted so long it felt like a one-act play!) I leaned forward and pressed my cock against Becky's now wet and sticky breasts and gurgled out the last of my semen. As I was finishing, Becky was just starting to come and I saw her clamp her legs around her hand as she fell back on the couch and she let out a series of moans, groans and 'Oh my GODs' as she came.

I plopped back down onto the couch next to Becky and held her tight. After we caught our breath, we smiled contentedly and commented on how absolutely unbelievable our orgasms had been. She noted the amount of semen I produced and I told her that when I don't masturbate for several days, and become highly aroused, I could drown a small cat with the amount of come I shoot. She thought that was unbelievably funny and it took her a while to stop laughing. When she did she suggested we go in to the bathroom and shower up. I thought she wanted to do it individually, but she invited me in with her.

As I stepped into the shower behind Becky, I teasing put my hand on her rather large butt (large for a woman of her stature; she actually had a rather slim waist so I guess she is what is considered somewhat 'pear-shaped'). She giggled and slapped my hand. As she began to rinse my come off her chest and out of her hair, I took a handful of conditioner and slicked up my penis, which had already grown hard again. I placed it directly into the crack of her ass, and reaching around, I took the soap and began to wash her breasts from behind. She instinctively began to grind back against me, causing my cock to slide up and down her ass.'Play with yourself, again Beck. Let me see you come again' I breathed into her ear. She tilted her head back and kissed me fully on the lips as her hand quickly went between her legs to masturbate for the third time in less than an hour. I continued to massage her soapy breasts as she ground her ass against my cock. The visual and feeling of my hands on her breasts, her hand frantically rubbing her pussy and my cock sliding up and down her ass was too much for both of us. This time, though, she came first - while her tongue was planted firmly inside my mouth. Her grunts and groans were like an aphrodisiac to me and as I slid up and down her large behind, I gently pushed her forward to she was bending over slightly at the waist. I looked down and saw my penis gliding up and down her beautiful, full pale ass, and I began to come again - not quite torrents this time but still very intense (and messy - although not a problem in the shower...!). I ejaculated all over her back and ass. I hadn't orgasmed twice in such a short time, and in such quantities, since I was a teenager. It was unbelievable.

We finished our shower, went out and had another slice of (cold) pizza while watching SportsCenter (my kind of gal - she actually likes sports!). As the evening got later, we both became tired until I finally had to leave. We locked in a passionate kiss and embrace at the front door, and Becky thanked my profusely for making her feel so good. She also reminded me, and I agreed, that this was a one-time only affair. While this happened almost a year ago to the day (Aug 9, 2002) we remain good friends and our banter is still good natured, although a lot more sexual in nature than in the past. She has been dating a guy from her church quite seriously now for about 7 months, and she has told me that the sex is awesome (although she hasn't shared any details). My sex life, in the meantime has picked up dramatically as I've taken the bull by the horns and initiated sex 3 times a week with my wife. Last night she jerked me off while we were sitting naked on a lounge chair on our deck - something that even I find a bit risky since we have houses on 3 sides of our property within 50 yards of where we were sitting.

More stories to come.

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