Losing and Winning

"That was incredible, my love...I can't remember the last time I came that hard."

"Now it's my turn...take me to bed and fuck me...."

And that I did. She pulled me to my feet and guided me to the bedroom, and to her hot steaming body. Having just come let me have some patience and stamina, and I stayed hard and gave her the fucking she demanded.

The next day, Ann called me and thanked me for the dinner and the movie and asked me how the rest of my night was. I told her that she was welcome and that it was just fine.

"So what did you guys do after I left," Ann prodded, seeking more details than my vague answer.

"You know...we finished what we started," I said, still not quite sure how much she needed to know.

"You know that wasn't fair that you guys were playing around with me just there on the sofa...made me horny too..." Ann said, her voice starting to take on that lusty timbre that I heard last night.

"Well, it wasn't exactly planned...sorry to be rude. Bonnie just got a little adventurous. What did you do last night?" I countered, trying to change the direction of the conversation.

"I went home and played with myself, thinking of you two getting it on." Ann frankly responded, without any hesitation in her voice at all.

"I see..." I smartly said, not exactly expecting that from her.

"Feeling you between my feet and then thinking of what you guys might have been doing made me horny. It's been a lot of months since Will died, you know...and I've been lonely and horny. It's kind of a drag, you know?"

"Sorry about that Ann...we should have been more discrete."

"No, don't worry...it gave me fuel for my imagination."

"Did Bonnie take care of your needs Joe"

"Yes, she did."

"Tell me how," Ann persisted, seeking details.

"That's kind of private Ann."

"C'mon Joe...I need some kind of spice in my life, even if it's vicarious."

I paused for a couple moments, thinking about how much she 'needed' to know and how much I could tell her.

Sensing my hesitation, Ann said, "just a few details Joe...that's all I ask. I'm sure Will shared some things about us when you guys were out doing what guys do."

"No Ann...nothing like that."

"Now I know that's not true Joe...Will told me everything...I think he told you more than you let on. Now it's only fair that you tell me a bit...give a poor, lonely, horny girl a break, will ya'"

"OK Ann...so when you left, Bonnie resumed what she had started on the sofa and gave me an incredible blow job. It had been a few days for us, and combined with what she—and you I might add—were doing to me, it made for the most intense orgasm I can remember. And then we fucked like crazy until 2 this morning."

"Now, that's better. I'm glad I could have been of some service. Does Bonnie give good head?"

"Oh yeah...not often enough, but when she does, it's great. You know what they say...there isn't anything like a bad blow job."

"That's hot Joe...I'm glad for you. Did she let you come on her or in her mouth?"

"Boy, you really want details, now don't you?"

"Yes."

"She asked me what I wanted, and last night I wanted to see myself come on her. So that's what we did."

"Hot stuff Joey...hot stuff. And did you make her come too?"

"I sure did Ann...a few times I think."

"Did you go down on her or did you just fuck her?"

"I did both."

"Good man...a woman needs both too, you know."

I found myself quite hard and aroused by this conversation. It was way more sexual than any other conversation we had had, and I also found myself enjoying telling her all these details.

"Thanks for the details Joey...I like knowing that about you guys. I promise I won't tell Bonnie that you told me all this stuff...scouts honor..."

"Yeah...I'm not sure what she would think of this sort of conversation...I confess that I enjoy it."

"Does that mean you're hard?"

"Um...yes, it does."

"Well, it makes me wet as can be Joey...so thanks."

"You're welcome..."

"Well, gotta go. Thanks again for the dinner and movie...and especially for the conversation and the images. You're making me horny all over again."

"You're welcome again. Sorry I can't be there to help with that." I don't know where that reply came from, but I guess it was my dick talking.

"Joey, I don't think you can handle me...I can get pretty crazy when properly motivated."

"I know...Will told me."

"See, I knew you guys talked about that stuff more than you let on."

"Well, perhaps he said a little...take care Ann. Have a good day."

"You too Joey...keep that Bonnie happy And thanks for sharing some stuff with me."

"I will. Bye."

The next couple weeks were busy for all of us, and we didn't get together the next week for a movie night. We did do some running together with the whole crowd, and other than a couple smirks from Ann when she saw my hard on after stretching, and a couple text messages with some mild sexual innuendo, all seemed back to normal.

Bonnie and I were fighting a bit more since that night over small things. Seemed so odd, but our lives seemed to be moving apart and we were both finding small excuses to not get together. And the following week, she had to go out of town for a week on business and to visit her family. So Ann and I decided to hang out at my place again. She said she would bring the movie. I told her Bonnie won't be joining us.

The movie she picked was some crappy, sappy love story thing, that about half way through, even Ann thought was too stupid to waste more time on.

"How about we bag this movie Joe...even I can't stand it."

"Sounds ok to me. Want something else to drink?"

"Sure what have you got?"

"Beer, wine, something stronger perhaps?"

"How about some whiskey?"

"Gee Ann...I never knew you went for the hard stuff..."

"In more ways than one Joey...I thought you knew that," she replied with a smirk. I guess I set that one up rather well for her.

So I got us some good whiskey and a couple glasses. We sat around sipping and talking about stuff. I told her that Bonnie and I were fighting a bit and that she was pissed at me for something that I did or didn't too. I couldn't tell which. Ann said that women were complicated in that way, and it was on purpose to keep men guessing.

"Want to play cards?" Ann then asked.

"Sure...be right back." A moment later, with cards and chips, I asked, "What's your game?"

"How about gin rummy?"

"Sure, sounds fun. First to 500 wins."

So for about an hour, we played gin and drank scotch. Now I've played my share of cards and gin wasn't my game. But I was getting some good cards, and before long, I made it to 500 points with a comfortable margin.

"You sure got some good cards Joey...how about some poker. Let's see if your luck holds out there too."

"Fine by me." We were both a little drunk by now, but feeling quite fine. I've also played some poker before too, and I was hoping my poker was better than my gin, especially with the lucky cards that I've been getting.

I split up some chips and we were about even for the first few hands. I was trying to gauge her skill and her blood alcohol level. After a couple more hands, I could get a sense that she bet a little erratically and not really with the cards she had. Plus, I think after a couple refills of the booze, there was more booze than ice.

"How about we up the ante a bit Joey...this isn't fun."

"So what are we talking here? Want to put some cash on the table Anne?"

"No...I was talking clothes...strip poker. Ever played that before?"

"Sure I have. That makes things interesting to be sure."

"I guess we have on about the equal number of pieces...you game?"

"Sure I'm game. Let's see what you got"

"Deal 'em smart guy..."

The first hand went to her with a lucky pair of jacks to my pair of 5's, and I lost my shirt. The next hand I won with drawing a pair of 6's with my pair of 9's; she had nothing. Then her shirt came off and she was looking at me looking at her bra and nipples protruding proudly and plainly visible through the sheer lace.

"Nice stuff Ann..."

"Keep your mind on the game. You haven't won yet. Just one hand."

"Now I'm properly motivated...better watch your cards."

"Keep dealing Joey..."

So the next hand was a little more distracting. I was watching her breasts rather than her face for her expression at her cards. I had four hearts and drew one for the flush. She threw down a pair of kings and stood looking at me, and slowly drew down her shorts, revealing those long legs that I'd so admired for months from running and the blue lace panties that matched her bra.

"Now we're talking Ann...nice undergarments...a little cold in here?" I commented, pointing to her nipples.

"No smart guy...just a little turned on."

"Good. Ready for the next hand?"

"Sure...you're not quitting, are you?"

"Why should I quit...you're the one in your underwear. I seem to be on a roll."

The next hand was a little less promising at the start, and since we weren't bluffing, we had to just play the cards. I got dealt nothing, and decided to keep the high queen and king, and drew three cards. I got a pair of queens. Ann had nothing.

Without much ado, she reached behind her back and unclasped her bra. With me completely staring blatantly at her chest, sipping the drink, I watched intently at her breasts as they came into view. She had marvelous full and firm breasts with very erect nipples. I couldn't believe after all this time I was finally getting to see her almost naked. She was quite the sight...flushed with excitement and alcohol, standing in front of me in sheer, light blue panties. I could smell her scent, a combination of her perfume that I've smelled before, but combined with her excitement I was beyond aroused at this point.

"Speechless for once, eh Joey?" she said, proudly displaying her toned body before me. She was looking right at me as I was plainly staring at her 90% naked form.

"You're beautiful Ann..."

"Thank you Joey..." She sat down and I was just staring some more. "Aren't you going to deal again? Or are you having a hard time concentrating?" With the word 'hard' she glanced down at my shorts, also plainly indicating my arousal.

"I think I can manage...seems the cards are rolling in my favor after all."

She held her drink, swishing around the ice and bronze colored contents, and with a sexy and sultry pose, sipped away as I shuffled the cards and watched her breasts rise and fall with her breathing. I think I lost count of the number of times I shuffled, I was so distracted by looking at her beautiful body.

"Are you going to deal or play with the cards all night?"

"Patience...I was going to say, 'keep your pants on', but you've lost them already, haven't you?"

"We'll see who loses pants...deal 'em."

The next hand, I had a pair of 3's at the start, and drew three cards. I got a third three, which was better than her pair of 10's.

"Damn it...aren't you the lucky one tonight...I've only got one thing left to bet here...what are we going to play with next?" she said, slowly standing and looking at me while she bent over and slowly rolled her panties down her thighs, to her legs and off her feet. She stood in front of me proud and sexy, completely nude. She was mostly shaved, just with a thin patch of hair at the top of her pussy, which was glistening with her arousal.

"God, you're incredible Ann...I always thought you were sexy, but this is so hot..."

"Thanks Joey...I knew you were looking at me when we run and stretch...I hope it was worth the wait."

"Oh, that's for damn sure..."

"So still feeling lucky? How about another hand?" she asked.

"Sure...I'm on a roll. What are you going to bet with though? Seems you're out of clothes."

"I'll think of something...deal 'em."

I shuffled again a few more times than normal, staring at her complete nudity, sipping her drink, smiling at me and enjoying my staring at her without hesitation and without any sense of embarrassment on her part.

"So how about if I win, you take all off. You win, I'll touch myself and you can watch. How's that?"

"I'm good." My mouth was getting dry and I was trying hard to keep my head clear from the alcohol so that I could remember all that was happening and get one more hand from her.

I was barely paying attention to my cards, and I had a pair of 2's, and drew nothing. She laid down a pair of kings, and smiled a wide grin.

"Now it's my turn to watch...seemed like you were just getting too lucky. Off with the clothes Joey."

I was a bit more embarrassed than she seemed to be, and I stood and dropped my shorts and underwear, standing naked and erect in front of her.

"Nice stuff Joey...just as I remember..."

"What do you mean?"

"Don't you remember my foot on you a few weeks ago at our movie night...I had a pretty good view then too, and my feet have a good memory..."

"Oh yeah...that was naughty of you Ann to torture me like that."

"I don't remember you complaining. And you said you had a pretty good time after I left too."

"Quite right..."

I sat back down on the soft and watch her looking at my body the same way that I ogled her body, with lust in her eyes. My cock was rock hard and sticking straight up in the air, and leaking a bit of pre cum as well.

"This is pretty crazy Ann...I'm so turned on now...but I also feel a little weird like this in front of you. We've known each other as friends for years, and I 'm also in a relationship with Bonnie..."

"I know... me too. I don't want to be the home wrecker. But I've been so horny Joey...it's been months and months for me. And I'm wet as a rain storm..."

"Since the time you told me you went home and played with yourself, I've fantasized about watching you masturbate...perhaps we can keep our distance a little and just watch each other?" I offered, trying to battle the evil guy in one ear yelling for me to fuck her and the other ear hearing the voice of reason. "That's an idea Joey....that would be safe and not constitute cheating, would it?" Rationalization can be a good thing.

With that, Ann leaned back against the end of the sofa and drew one leg up to the back and let her other leg on the floor so her pussy was open to my intent gaze. I could see her arousal and her inner thighs were shiny with her juices. I could very much smell her scent now and the combination of this view in front of me and her scent made my senses swell with their power.

I too leaned back and watched her slowly stroke her breasts with one hand and her outer lips with her other. I grabbed the base of my cock and was careful not to start stroking right away, for fear that in about half a minute, I would come.

"That's hot Joey...I've always loved watching guys stroke themselves. Don't come too soon though, ok?"

"OK...you're so sexy Ann...I love watching you do this. It's sort of a fantasy of mine"

"Me too...helps fuel the visual fire, huh?"

"Yes indeed..." She started slowly stroking inside her outer lips and her pussy was absolutely dripping wet. I could see her juices on her fingers as one delved deep into her pussy. Her other hand moved down to hold her self open to me, as the other hand started stroking light circles around her clit. "You're so hot Ann...is this what you did the other night too? Just like this?"

"Sort of...that time I just needed to get off...no preliminaries...just a quick rub and I came in a minute."

"I didn't think girls were able to come quickly like that...I thought it was just guys."

"Like I said Joey...when properly motivated, I can get quite crazy. And that time, I was way properly motivated. I had these visions of your cock between my feet and watching you come all over my feet had me crazy and coming in hardly any time at all."

I'm sure the free speech was in large part due to the alcohol that we were drinking. But hey, we weren't cheating, were we? I started stroking my cock now with slow, firm strokes and I knew that I would be coming in a minute too, if I went too fast.

"Is this how you jerk off Joey? Do you stroke yourself like this?" Ann asked with that low, sultry voice that I've now heard a couple times. Her gaze was firmly planted on my hand rubbing my cock, as mine was at her pleasure center, watching her hand and fingers expertly bring her self pleasure.

"Mostly...it's not real tricky...I can come real fast too. And I think this situation constitutes proper motivation for me too..."

"Maybe we can come at the same time, huh? Want to try?"

"Sure...won't take long for me...watching you is so hot Ann..."

"Just not yet Joey...I'm enjoying this too much."

"OK. Me too."

"I can see your pen's leaking..."

"Yeah...it kind of does that when I'm really turned on."

"Me too...this is so hot Joey...it's been a long time for me...this isn't quite like a good hard fucking, but it's close."

"Speaking of close...I am. Ann...I need to come soon...it's been a few days for me, and you've had me turned on almost all night."

"Bonnie isn't taking care of things like she used to, huh? Poor thing. Did you have to take matters into your own hands, then?" Ann asked, now intently watching my hard cock leaking and pumping in and out of my hand. My hips were now instinctively moving a bit too, getting closer and closer to the inevitable.

"Like I said, things have cooled down lately. I'm not sure why."

"Did you jerk off earlier this week?"

"Uh huh...a few days ago."

"Just like this? Were you thinking of me playing with my pussy when you did?"

"Well, sort of..."

"You can tell me Joey...what were you thinking of when you jerked off?"

"I was thinking of you sucking me off and me coming all over you." Again, the alcohol plus the naked beauty in front of me removed all inhibitions.

"That's naughty Joey...that's so naughty," she whispered, hoarsely. Her breathing was quick and a bit labored with excitement.

"What were you thinking of when you played with yourself?" I countered.

"Actually...something rather like this..." she confessed. "Joey...can I ask you something else?"

"Hasn't stopped you yet..." I managed to reply, still trying not to come. I was purposely stroking myself slower than normal because I knew I would come soon.

"Will you do that...I mean, will you come on me?"

"You want me to?"

"Yes...please. Slide closer to me. I'm almost there Joey...please..." She turned to sit facing forward on the sofa like the way I was sitting and scooted closer to me. I too, slid towards her so that our legs and arms were touching and I could inhale her scent even more. I could feel her right arm against my side, moving with the rhythm that she knew best. My left side was against her right side, and we were both looking down at the other's quickening hand motions, bringing us closer and closer to our much needed releases.

"This is so hot Ann...I'm going to come...I can feel you getting closer too...you smell so good..." I moaned and with a couple more strokes, I leaned in towards her and groaned as my cock shot forth volley after volley of hot come onto her body, the first landing with a splat onto her shoulder, then her right breast and then her stomach, rolling down her body.

"Oh god Joey...I'm coming too..oh god...oh...oh..." she moaned and her fingers quickly strumming her clit to an orgasm that erupted just after my come hit her skin. I could see her legs clamping together as she brought herself off, as she knew best.

I leaned my head on her shoulder as my orgasm subsided and a few more spurts of come landed on her elbow and her side as I stroked my hard cock, pulling the last drops out of me and onto her skin.

We both were breathing heavily as we came down to earth. I was savoring the sensation of her body against mine and the smell of our mutual orgasms. Her left hand came across her body to rub my come into her skin, causing it to glisten further mixed with her perspiration. The sight and smell were so erotic I was trying hard to take it all in and commit this to permanent memory.