Losing and Winning

Will and I were great friends for years. We had gone to college together and through sports, mostly running, developed a great friendship that sustained college and some years after. I got to know his family and friends, and then ultimately his girlfriend who became his wife Her name is Ann. Since Will and I were from the Northeast, we did end up with jobs there after college and stayed in touch, though no doubt, he ended up being his wife's husband first and my friend second.

Nonetheless, we three did lots of things together, and when I was with my girlfriend, we made a pretty consistent and friendly foursome. One of the things we did a lot together was run. Getting into our late 20's, and busy with professional lives, we found a common outlet in running and joined a running club together, that met after work most weekdays, and for long runs on the weekends. Ann didn't always join the long runs, but Will and I would start with Ann joining us, and then she may drop off with some others to join us at the end for some post run stretching/cool down stuff. I always loved looking at her long, lithe legs with the short running shorts that showed off her toned calves and smooth legs...right up to her amazing ass. It gave me the occasional partial boner just looking at Ann and Will stretching together, because of the multiple erotic and quite inappropriate images that were running around in my head. I had to stretch more so that I could get distracted. Running gear doesn't leave too much for the imagination. Or rather, if quite fuels the imagination...

Now Ann was really quite amazing. She was about 5'6", long brown hair and a super body and personality. She was always so easy-going and just always a nice person and fun to be around. Will would joke and say that even though she's so nice, she can be quite the unexpected tigress in bed. That was one of the things that attracted him to her at the start. She just came across as the typical 'girl-next-door' type, but then she was just this amazing sexual creature when they were alone. Sometimes, when properly prompted or when he was a little drunk, he gave more details, which fueled my imagination... like her propensity to make him come on her, and her love of oral sex, both giving and receiving. Those stories that he told, mostly when we were out drinking and the subject came up among the guys, really created some crazy powerful images in my head that were sometimes hard to get out when we were all just hanging out socially.

We did lots of stuff together, including eating out, going to each other's house for dinners and parties, and then we started a movie night where all 4 of us rented a movie and had a dinner/movie thing. I was in a mildly serious relationship with Bonnie, whom I met through some other friends and we had been dating for about 6 months, and all got along quite well. Nothing terribly serious for me, but I think Bonnie wanted more from the relationship than I did at this point. But we all had fun together, and had lots of laughs.

Anyhow, we were training for a half-marathon, and the group would do 15 mile runs on Saturdays, in addition to about 15 miles during the week. Several members were working towards that race, and sometimes pushing each other real hard. I had to miss one week for a business trip, and I had a phone call one day from Ann just a day before I was coming home that changed our lives.

Ann and Will had been married for about a year at that point, and all was going so well for them. Ann called me one evening on my cell phone when I was in the hotel getting ready for an evening meeting, and the sound of her voice made me stop in my tracks.

She had obviously been crying and I could hear her voice crack.

"Joe...I've got some bad news..." she said slowly and full of sadness.

"Ann, what is it? Are you ok?"

"Joe. Will is dead."

I literally had to sit on the bed because the air was just sucked out of my lungs. I couldn't even fathom that this was reality.

"Ann, are you kidding? What happened?"

"Joe...he just died today. They think he had a heart attack or something..." and she started crying all over again.

"Ann...tell me what happened. He was a fit as anyone I know...how can he have had a heart attack? That happens to older people with bad hearts..."

"I don't know yet...I just came from the hospital and they called me and said he was brought there after running and had collapsed. It's been so hot here and he and the guys were running and they said he just collapsed...They called 9-1-1, but there was nothing they could do..."

"Oh Ann...I'm so sorry...I just can't believe that...I've know Will for 10 years, and never known him to have anything wrong with him whatsoever..."

"Well, apparently he did have some congenital condition that was supposed to be mild and never cause any problems. But he just got overheated and...now..." she started sobbing all over again. "...now he's gone Joe..."

I was horrified, shocked and devastated by this news. I had lost a friend and Ann had lost her husband. These things weren't supposed to happen. We were young and had lives to look forward to and families to raise and so much in our futures, that we don't for a moment, consider that one day and one moment, our lives can be simply over. It doesn't seem fair and it certainly didn't make any sense.

"Ann...I'll be home first thing in the morning. Is there anything I can do for you? Is Joe's family notified and coming in?"

"Yes...they called me first a few hours ago, and then when we knew there was nothing more that anyone could do, the doctors and I called his folks and sister. They're coming in tonight."

"Ann, thank you for calling me yourself. I can't imagine how this is for you. I'll help in any way I can."

"Thanks Joe...you were always his best friend, and I just feel so sorry to have to tell you and so sad that we've just suddenly lost our Will..."

So in the ensuing weeks, the funeral was done and we so mourned Will's life, then celebrated his life and cherished the memories. He was such a fine man and a good friend to me and husband to Ann. Ann, Bonnie and I continued to hang out because we wanted to support our friend and keep her company and be around in her sad times.

We tried to keep the movie night thing going, just with the three of us. Weeks turned into months and Ann seemed to be dealing as well as can be expected. She had returned to work and had family and friends giving her as much support as we all could and as much as she seemed to need. The movie nights, though sad with 3 instead of 4, did seem to give all of us something to look forward to each week.

There were many nights that just Ann and I hung out because of schedules, and talked of many things, including Will and she seemed to be able to laugh more and was not so sad all the time, at least not in front of me.

"I still cry a lot Joe...I miss Will and all the plans and memories that we had together," she once said. "But I can laugh now too...I wasn't sure I'd ever laugh again."

"I know Ann...I'm glad to see you smile more these days. You are really a special woman and I admire your strength."

Ann started to return to her normal activities that she did when Will was alive, including the running club. She was initially a little out of shape, and so ran just part of the way with the group, who were all incredibly supportive of her recovery, both emotional and physical. And the weeks went on, she got back up to speed and ran with the group. At the end of the runs, she and I would often pair up to do our cool-down stretches, and I found myself returning to the prior thoughts of her close physique and I was trying real hard not to ogle inappropriately and keep my thoughts pure. But her long, muscular legs and the short running shorts and her scent of perfume mixed with a little sweat did little to assuage my vivid imagination.

I wasn't sure if she was trying to be subtle, but the hurdler's stretch that we did, which is sitting on the ground with one leg out front and the other leg tucked back was one particular maneuver that did little to hide her legs and thighs, and even exposed some very inner thigh, right up to her crotch and I could see the contours of her mound, when I could sneak a peek of longer than a stolen moments glimpse. I swear I could see her smile a little when she caught me looking, but she did little to obscure my viewing angle. And I swear her nipples would harden a little when I tried to hide the bulge in my shorts and make some excuse to turn away so that she wouldn't see my erection poking from my shorts. And one time, she stood and gave me a quick hug before I could walk away and I know she had to feel my swollen cock against her stomach.

Though many of my nights were filled with Bonnie and a very active sex life, my thoughts strayed to Ann and her playful antics and flirting moments, and the memories of Will's descriptions of their sex lives together all combined to make my head spin with illicit thoughts of Ann with me, and how she would feel under my hands and between my legs and in my lips.

So one movie night at my apartment, it was my turn to chose the movie and it was a thriller sort of movie with some action and complex plot that you had to pay attention to, to figure out who's the good guy and who's the bad guy. Pretty much a guy movie, but I'd sat through enough chick flicks that the girls could watch this one with me.

I think Bonnie had lost interest in the movie early on and seemed rather playful and a bit tipsy from our wine with dinner and after. Bonnie and I sat under a blanket with our feet on the ottoman, and Ann was on the other side of the sofa, also curled up under another blanket. Bonnie curled up against my shoulder and was rubbing my arm and then my chest, knowing full well that my nipples are sensitive and makes me harder than hard. Then she started down my stomach and beneath the blanket, stroked my thigh and eased her hand over my cock, now quite hard and eager under my shorts.

Then she eased her hand up the open leg of my shorts and started playing with my balls and stroking the exposed length of my cock. All the while, she feigned partial interest in the movie, as I struggled to maintain some composure and tried to hide our actions from our guest, who was just a few feet away on my other side.

I tried to concentrate on the movie, but I was starting to sweat with the pleasure that Bonnie was giving me, and all the while, Ann just next to me appearing for all intents and purposes, to be watching the movie. I tried to glance over at her to see if she could see what was going on, but I couldn't make out her face in the darkness of the room.

Then Bonnie upped the ante, and deftly unbuttoned my shorts and unzipped my fly and extricated my aching cock from its confines, all with one hand, and continued to tease me without mercy by sliding her fingers softly and slowly over the head of my cock and at the groove on the underside. She knows what buttons to push with me and she knows that this drives me crazy without the firm stroking that she knows will make me come. I know I was breathing erratically and trying so very hard to stay quiet and discrete. Every once in a while, Bonnie would firmly grasp my cock and stroke me a couple times and feel my cock throb in her hand, but still not make me come. I'm not sure what was the worse tease, her constant slow caress of my cock or the deliberate stroke that held me on the brink of orgasm for almost an hour of the movie.

At a slow point of the movie, Bonnie asked if anyone wanted some popcorn. Ann said that she'd love some, so I paused the movie and Bonnie just quickly got up and left me there with my shorts pushed down my legs and my hard and dripping cock exposed just underneath the blanket.

"So Joe, are you enjoying the movie," Ann asked.

"Yeah...sure. How about you?"

"It's a little violent for me, but it's got an interesting plot. You seem a bit distracted though...aren't you liking it? You picked it out after all..."

Meanwhile, I heard the cupboard opening and the microwave oven humming making the popcorn.

"Yeah, the movie is good..." I tried to be vague because after all, I was being tortured with the most blissful and secret hand job just feet away from Ann. I know I couldn't intelligently discuss the plot whatsoever.

"You guys must be hot under those covers...it's not all that cold out now," Ann said, and slid her feet towards me to pull the blanket away from me with her feet.

I sort of panicked that she would succeed and expose my naked loins to her and she would find out about what Bonnie and I were doing just a moment ago.

"No, I'm good," I quickly stammered. "I like being under the blanket."

So Ann didn't get the blanket off me, but did get her feet up against my thigh underneath the edge of the cover.

"How about a foot massage until we start the movie back up?" Ann asked, sliding her feet up into my lap. "I've been walking around in heels all day."

I tried to push her feet from my lap, for fear of having her feet encounter my naked and throbbing erection. But she could quickly assess that my shorts were bunched around my waist and that my lap was encumbered by my cock, sticking straight up in the air.

"My, my, my Joe...what have we here...so you must really like the movie, or you and Bonnie are playing around a little..." Ann teased, as the back of her foot rubbed up against the undersurface of my cock. "Maybe it's not my foot that needs the rubbing after all..." she further said, with a slightly more lusty voice, as her other foot joined the first one and clamped around my cock.

"I knew you guys weren't exactly watching the movie...I could see Bonnie's hand moving up and down in your lap...it's very naughty of you guys to be doing this right next to me and all...I'm not blind..."

I could hear the popping start in the kitchen, indicating that the popcorn was getting cooked...as was my cock now encased between Ann's soft feet.

"Sorry Ann...didn't mean to embarrass you...Bonnie just gets a little playful when she has a couple drinks..."

"I'm not the one embarrassed Joe...it's you with the erection now between my feet..."

She continued to stroke my cock with her feet, bringing me incredible pleasure and even if I thought of stopping her feet from their intended course, the sensations of her bare feet on my bare flesh were enough to hold rational thought at bay.

"Have you ever had a foot job before Joe?" Ann asked softly and tenderly. "It's quite fun...for both parties I think. Did Bonnie leave you hard and wanting Joe? Did you want her to finish you off beneath the blanket? Now that would have been really impolite to your guest...and I'm not sure you could have kept that a secret from me, could you?"

I'm pretty sure that those were mostly rhetorical questions, because I was powerless to stop this most sensual foot job by my friend with my girlfriend popping popcorn just down the hall.

"That would have left quite the mess, wouldn't it....were you close to coming Joe, when Bonnie left? Do you like my feet on you? It's been a while since I've done this, but I think I remember what to do..." Ann's voice was asking some questions that I had a harder and harder time comprehending, as I was mesmerized at the feel of her feet stroking my cock.

I just nodded my head, without uttering a word, for fear of interrupting her motions and spoiling the moment.

"You'd better not come now either Joe...that would be a bit hard to explain, now wouldn't it?" Ann's voice was mesmerizing and low and lusty...nothing like I've heard from her before.

But she didn't stop her relentless stroking, now both feet encasing my shaft with the soles and insteps of her feet, providing a strange but erotic sensation in me. I could hear the popping getting closer, and I could smell the popcorn now.

"You feel great Joe...I've always wondered what you would feel like against my skin. I'm not sure I pictured it exactly like this, but this is very sexy..."

I pulled the blanket down so we both could look at the action unfolding in front of us. I was just dying to see her small, smooth feet and painted toes wrapped around my cock. And the vision didn't disappoint. The soft glow of the TV allowed a surreal image of my 8" cock encased by small feet like hands stroking up and down the length.

"Oh God, Ann...please..."

"Please what Joe...please stop or please finish...?"

With that, the microwave beeped its cycle completed and Bonnie's footsteps were heard just a few yards away coming down the hall.

I looked pleadingly at Ann, and she took her eyes from my cock between her feet and slowly moved them away just in time for me to cover up and her to replace her feet in front of her as Bonnie came with a bowl of popcorn for us three to share.

"Here we go guys...let's dig in and restart the movie." Bonnie said cheerily as I grabbed the remote control and tried to digest the last 5 minutes. It was hard to concentrate on the movie with the popcorn being passed around, the movie starting and my aching cock that had been teased for the last hour by my girlfriend's hand and my best friend's feet shortly thereafter.

When the movie finally finished, Ann rather quickly excused herself, and headed home. Bonnie lost no time and knelt between my legs and removed my cock that remained partially hard, and started stroking me again. I was back to rock hard in no time and Bonnie looked up at me and held my eyes with hers as she took my into her warm mouth and started sucking me deeply.

"Oh Bonnie...this won't take long like this...you had me on the verge of coming during that movie for almost an hour...that wasn't fair, you know...with Ann right there and all."

She simply nodded her head, keeping my head in her mouth and stroking the shaft.

She slowly removed my from her mouth and said, "I didn't hear you complaining though...you could have told me to stop..."

"I didn't say I wanted you to stop...I just said it wasn't fair. And I think Ann knew what we were doing too."

"So what if she did," Bonnie smiled, while continuing to stroke me. She resumed sucking my cock, now deep into her mouth. I was starting to feel myself getting ready to come, even though she had only been sucking me for a few minutes.

"Bonnie...oh god...I'm gonna' come...keep sucking me like that...you know that makes me crazy..."

Again, she nodded her head and looked up at me with her mouth stuffed full of my aching cock, ready to explode.

She stopped sucking for a moment and looking at me said, "You've been a very good boy Joey...do you want to come now? Do you want to come in my mouth? Or do you want to come all over my tits?" Her hand continued to firmly and deliberately stroking me up and down, my shaft quite wet with her saliva.

"On you," was all I could muster for a response, given the duration of my teasing up to this point.

"Oh you dirty boy...I know how you like to cover me with your come." She quickly removed her shirt to expose her braless breasts, and resumed sucking and stroking my cock, dripping and aching with need and imminent release.

In just about a minute more, I moaned and groaned that I was going to come. Bonnie knew the signs by then, and looking up at me, stroked and coaxed the most intense orgasm from me in years. I yelled and shot three or four times hot, thick bursts of come onto her face and neck, hearing the splash on her skin, and watching the come spurt then onto her breasts and then onto her hand, matching the rhythm of my spasms.

With my cock still hard in her shiny hand, and her face and neck and breasts covered with my come, Bonnie looked at her hand wrapped around my cock, then down to her soaked chest, and then up to me. "My, my Joey...that was a lot of come...has it been that long? I guess I'll need to take care of you a little more often, then, huh?"