Playdate

Our little group meets twice a week. Our kids play and we drink and bitch about our kids or our exes or our jobs, or whatever else we have to bitch about.

There are 6 of us here. Jackie, Jennifer, Maxine, Karen, Samantha, and me, Jonathan. When I found the craigslist ad I didn’t realize I would be the only guy, and I’ll be the first to admit that some days you can just choke on all the estrogen in the room, but we all get along. We share a common thread. We are all broken things that are attempting to appear whole for the sake of our children. And twice a week we can let go of that illusion for just a moment and try to feel something real.

It was Karen who started the game of Truth or Dare. It’s her kind of thing. A “Trust Exercise” for the group, or maybe that’s just how we justified it afterwards. I think at the time we were just a bit to drunk for our own good. Or just drunk enough for our general well being. Something like that. The kids were downstairs with a new video game and pretty much guaranteed not to come up unless someone lost an eye or something.

And Karen said “Lets play Truth or Dare!” And Maxine said “I think you’re in the wrong part of the house, Karen Dear, the pre-teens are downstairs.” And we all laughed but Karen rolled her eyes stood up to her full 5’6” and said “Don’t be a bitch Maxy, it’ll be fun. And we can all get to know each other better. Learn deep dark secrets and bond and stuff.”

“It won’t be any fun.” Maxine poured, “Jonathan won’t talk about his past, Jackie won’t talk about anything But her kids, and Samantha just lies about everything.” The last got a pillow lobbed at her by the afore mentioned Samantha.

She had a point too. I don’t talk about my past. My wife died, everything changed, and now I don’t live that life anymore. The only thing I had left from that life was a ring and the two boys downstairs. Why bring it up if I can’t bring it back?

“What if we could make sure everyone told the truth?” Karen asked. “What if we could be positive someone wouldn’t hold out.”

Maxine looked doubtful. She was the oldest in our group at 39 and tended to act like a mother hen. Not that she looked like one. She was a total gym rat, fed on a steady diet of ‘make the ex sorry he ever left me for that 25 year old whore.’

“No really, give me two minutes alone with each of you and I guaranty you’ll all be totally honest for the length of the game.”

“Ooooh are you going to hypnotize us into telling the truth?” Jennifer asked

“Actually, yeah, that was the plan.”

“Sweet. I’m going first.” and she jumped up and grabbed Karen’s hand and dragged her to the other room before she could say anything else.

And that was Jennifer in a nutshell. Young and perky and ready to jump off any bridge you put in front of her.

“You guys aren’t buying this are you?” asked Jackie once they were out of the room.

“I don’t know,” said Samantha, “it sounds interesting.”

“I’ll give it a try.” I said “What can it hurt?”

And then Jennifer was bouncing out and grabbing Maxine and dragging her into the other room. Chirping words of encouragement along the way. With Maxine safely delivered she came back to sit with us, fairly vibrating with energy. We all made small talk and drank as Karen worked her way through us.

When it was my turn Karen just poked her head out the door and called me back. The only light on was a small table lamp and Karen had me sit on the bed. She took my hand in hers and said “Jonathan, I’m going to hypnotize you now. It’s going to happen very fast and you are going to feel incredibly relaxed and refreshed when I’m done, but you won’t remember the middle bits. Are you Okay with that?”

“Yeah” I said

“Good, now I want you press down against my hand with yours, like you’re trying to pace your hand on your thigh, ok?” I nodded, my hand now against hers, palm to palm. “Now go ahead and close your eyes and just focus on your hand and know that as soon as you can touch your thigh you’ll be completely hypnotized and totally relaxed. Are you ready? I’m going to start counting, and with each number you’ll realize how much heavier you hand is and how much closer you are. " I nodded again and she said “One...” An then there was light and joy and a feeling of completion, and the my eyes open and she was saying “...refreshed and full of energy.” I blinked a few times and she stood up, my hand still in hers, and pulled me up and led me back into the main room.

I felt alive. I felt a level of contentment I hadn’t felt in years. And I heard Karen say “Jonathan, Truth or Dare?” and I said “Truth.”

“What was the last think your wife said to you?” She asked.

I froze. My contentment left me. I wanted to tell her it doesn’t matter, but a pressure was building behind my eyes. My chest tightened and my mouth went dry. And finally I said “I love your cock. I love your cock and I wish you could fuck me into oblivion.” It was like all of a sudden I was flying. My head was clear and I could breath again and every fiber of my being relaxed. “That’s the last thing my wife said to me. In her hospital bed, so thin I was afraid she would break and her voice barely a whisper she said ‘I love your cock and I wish you could fuck me into oblivion.’ and then she laughed and passed out again and didn’t wake up again and I’m sure somewhere out there she’s laughing her ass off because that’s just not a story you can tell people and she thought that sort of thing was hilarious.” I wanted to cry, but I just felt too good, like a small piece of misery had been burned away.

And that’s how it went, every time I held back, there was the pressure in my head, Karen’s little way to keep us honest. And I could see it on the others faces as well, the pain and then release. And eventually no one was even trying to hold back. We shared deep dark secrets and bonded and stuff. And eventually someone, Karen again, said Dare.

“Karen,” Jennifer asked, “Truth or Dare?”

“Dare.” Karen replied, a faint smile playing across her lips.

“Well finally somebody shows they’ve got a pair.” Jennifer said, with maybe a bit to much enthusiasm. “I dare you to show us all your tattoos.”

My eyebrows involuntarily went up. From earlier “truths” we knew Karen had 5 tattoos, and that none of those were visible while she was wearing her jeans and tee shirt. And Karen was in a word, hot. She was in her early 30’s 5’6” brown hair, green eyes, d cups, and an ass that wouldn’t quit.

And Karen didn’t bat an eye. She stood up and stripped of her shirt and bra in a single motion.

“One” she said and pointer to the biohazard symbol on her right shoulder.

I’m glad she said something or I might have spent the whole time just staring at her beautiful tits.

“Two” she now pointed to her left collarbone, Mandy, her daughters name written in a cursive script.

She was doing a little twirl as she went, making sure we all got to see.

“Three” the large dragon started with it’s tail between her breast, wrapped around her torso and disappeared into her jeans. Another smooth motion brought down her pants and panties. The dragon’s jaws opened over her shaved pussy, it’s tongue appearing to disappear inside her.

I was picking my own jaw up off the floor when she said “Four” and pointed to the thick tribal band circling her left thigh.

And “Five” a small butterfly on her right calf.

And just like that every thing went back on and she sat back down.

I looked around the room and everyone was as stunned as I was. Well, except maybe Jennifer. She looked rather pleased with herself.

Karen looked around the room “Who to choose?” Tapping her finger to her lips.

Look, look, look. Tap, tap, tap. Smile.

“Jackie...... Truth or Dare?”

Jackie put her face in her hands, her cheeks coloring. A barely audible “Dare.”

Karen made a high pitched sound and kicked her feet in glee.

“Jackie, I dare yoooooou tooooooooo... Lick Jonathan’s nipples”

“Whoa, what?” I asked.

“Don’t be a pussy Jonathan,” Karen said without looking at me, “this isn’t about you, just lift your shirt.” So I did.

Jackie is 26 and easily 6 foot, blond and supermodel skinny, maybe a B cup, maybe. She doesn’t work out, but between her jobs an the kids she gets a ton of exercise and hardly gets a chance to eat. She crawled over to me like a panther, and never taking her eyes off of mine, licked up my chest and over my left nipple. I shuttered and sucked in breath. She slid over to the other side and sucked my right nipple into her mouth, holding it between her teeth, and flicking her tongue across it again and again, sucking hard one last time and finishing with quick kiss on each one. I was rock hard and taking long slow breaths. Jackie crawled back to where she had been sitting to the whistles and cat calls of the other women. She never took her eyes off me.

“Jonathan, Truth or Dare?”

“ummm Truth?” I managed

“Truth? Really? Seriously?” she leaned back and crossed her arms across her chest “After that, Truth? Ok fine, truthfully, why the hell didn’t you pick Dare?”

Ok, I’m a pussy. I’ll admit it. I was embarrassed and afraid one of the kids was going to come upstairs. But those weren’t really the real reason.

Truth right?

“Because I haven’t had any real intimacy since my wife died. I haven’t gotten close to anyone. Us, here, now, this is the most open or connected I’ve been with anybody in over a year. And as fun as that just was, I don’t want to do anything to screw up this group and have to go back to being alone with my kids all the time. I love them to death, but I need to have adults to talk to or I’m gonna go bat shit crazy.”

My head was down I didn’t look at any of them.

“Jonathan,” Karen said my name softly “Two things, one, what do you possibly think you could do to get yourself kicked out, and Two, has it really been that long? You haven’t dated at all?”

“It’s not like I really have time to date, let alone get a sitter. And what am I going to do, hit the bars? Internet dating? I haven’t even stopped wearing my wedding ring. I can’t bring myself to take it off.”

“That’s one question, what about the other, what do you think you could do to ruin this?”

Did I mention Karen was a therapist? She was fun, and a little bit crazy, the tattoos were proof of that, but if you talked to her for any length if time, you got questions like that. “What makes you feel that way?” or “How long have you felt that way about yourself?” And you usually found yourself answering her.

“I don’t know how exactly, it’s just, I’m the odd man out here, man being the important word. If things got weird, went to far or whatever. I don’t have any delusions about who wouldn’t come back.”

“Jonathan,” Karen using my name again, locking eyes with me. I could feel her dropping into doctor mode.

“We are all friends here. If we didn’t feel safe with you, you wouldn’t be here. Your nice person who lost his wife and needs to reconnect with people. We all need to reconnect with people. We get isolated and locked into our kids and our jobs, and our other jobs. Everyone needs permission to be themselves sometimes. And sometimes we need permission to be someone else. That’s all this, a chance to let go, to let some one else decide what you’re going to do for the next 5 minutes. Can you do that, can you let go and let us in?”

“Yeah,” I laughed a little “I will let go.”

“Good.” Karen said “You’re up, who’s next?.”

“Jackie Tru” I started, but Jackie cut me off. “No tag backs Jon, sorry.” She said it teasingly.

“Ok then, Samantha, Truth or Dare?”

Samantha was sitting backwards on one of the chairs from the dining room. Leaning her chin on her hands.

“Truth.”

Oh thank god I thought. I had no idea what I would have asked if she’d said Dare. Truth though... I had a question I’d wanted to ask her for as long as I’d know her.

“Is that your real hair color?”

The thing is, Samantha had this amazingly bright red hair. She kept it short and I’d never seen roots, but I couldn’t believe it was actually her natural color, it was just too bright.

She gave me an annoyed look, even managing to raise one eyebrow, but she didn’t answer, she stood up. She took a deep breath and sighed. And then she unbuttoned her jeans and pulled them and her panties down to mid thigh. Her bright red bush shone in all it’s glory and she waved her had in front of it like a game show hostess. She did a quick turn to show the others and pulled up her jeans, rolled her eyes bowed deeply and sat back down.

Not exactly the answer I was expecting, but I can’t say I was disappointed.

The other women thought it was hilarious, it quickly went from giggles to actual roll on the floor laughter.

She arched her eyebrow again and said “Maxine, Truth or Dare?”

“Oh like I can top that with a bit of Truth.” Maxine said. “Dare.”

“It’s not a competition Maxine.”

“Everything is a competition Samantha Dear. It’s just a matter of accepting it or not.”

“Fine, then I Dare you to outdo Jackie, so you can ‘win’ or whatever.”

It was a playful challenge, but a challenge none the less.

“Okey-dokey, take off your shirt Sam.”

“What!?!” Samantha’s surprise at the turn of events was exactly what Maxine was going for.

“Sometimes winning means changing the rules Samantha dear, so please remove that pretty white top and anything you have below it so I can outdo Jackie.” The smirk on Maxine’s face was practically predatory, but Samantha complied, caught in her own Dare.

She unbuttoned her white blouse, her own smirk returning. Her bra had a front clasp and she unsnapped it, freeing her ample breast. Sam’s nipples were hard and dark against her pale skin. Her aureolas pulled tight and no larger than a quarter.

Maxine stalked up to her and slapped her left breast, hard. The sharp report was punctuated by Samantha’s intake of breath and ecstatic shudder. Maxine slapped her right breast and Sam’s whimper was the only sound in the stunned silence.

Maxine went to her knees and began biting her way up from Sam’s navel. She reached the left nipple and bit down with just her front teeth and pulled back, stretching the breast away from her body. A moan escaped Sam’s lips, her white knuckled hands gripped the sides of the chair. Maxine released her tortured nipple and gave the other a quick lick before returning to her seat, a Cheshire grin on her face.

Samantha was still shuddering but managed a breathy “okay, you win.”

Maxine leaned back, satisfied. “Jonathan, Truth or Dare?” she said, leveling me with a steady gaze.

“Dare” I said, afraid at this point to say anything else.

“Good. Go finish the poor girl off before she dies of frustration.”

“Wait, what?”

“What are you, 12? Give the girl a hand. Jonathan, I Dare you to give Samantha an orgasm.”

I stood up and walked over to her, uncertain of exactly what I should do. Samantha looked up at me with wanton eyes and bit her lower lip and mouthed please again and again.

I decided to follow Maxine’s lead. Hoping I’d made the right choice, I took a breath and grabbed the hair at the back of her head and tilted it back.

“Like this?” I asked, searching her face for any sign I’d done something wrong.

“Oh yes” she pleaded and so I let myself go. I gripped her hair firmly and kissed her roughly and she moaned into me. My free hand began reaching for her breast but she grabbed it and pulled it lower. I rubbed her sex through her jeans and she ground herself into me. I fumbled at her buttons and squeezed my hand inside her pants. She was sopping wet and my fingers slid easily inside her.

She grunted and thrust against me. I could feel her spasm around my fingers. The orgasm rippled through her and she shivered and sighed. I went to my knees and took her breast into my mouth, suckling at her as I continued to run my finger in and out of her and along the edged of her lips, occasionally touching on her now supersensitive clitoris, causing her to shudder again. I broke away from her to applause and cat calls.

“Seven minutes in heaven,” Karen commented, “is so much funner when you get to watch. You’re up next Jonathan, who do you choose?”

Samantha slid out of her chair and laid on the floor disheveled, half dressed, and basking in the afterglow of multiple orgasms.

This was hard. Hell, I was hard. Jackie was practically drooling on herself, but this was Karen’s game. Karen made the rules, Karen spurred us on. Karen took it to the next level and pushed us forward when I tried to pull back.

“Karen, what are we doing here? How far does this go?”

“We’re letting off steam and it goes as far as it needs too.”

“As far as it needs too? What the hell does that mean Karen?”

She leaned forward and looked at me hard. “Let me ask you question Jon.” She came over and kneeled in front of me, taking my hands in hers. “What do you want? Not tomorrow or next week, Right now, this very instant. No consequences, What do You want Jonathan?”

And I knew how good it feel to tell her the Truth. “I want to see you naked again. I want to taste every tattoo on your body and I want to fuck you until you look like Samantha, blissed out and incoherent.”

“That’s how far it needs to go Jonathan. We need to get what we want. Just for now, just for this moment, we’re all going to get what we want.” She sat back away from me then, back straight and hands in her lap, she said “Ask me Jon, ask me Truth or Dare.”

“Karen. Truth or Dare?”

“Dare.”

“...”

“You have to say the words Jonathan.”

I put my head down and stared at my hands. It was one thing to tell her I wanted her, it was another to ask her, hell, Dare her to fuck me. But it was the Truth, it was what I wanted.

“I Dare you to take your clothes off, and let me taste you. Let me kiss and lick and worship every inch of ink on your body and let me fuck you into delirium.”

She smiled at me. A wicked, mischievous grin full of promise and pulled her top off in one smooth motion. She stood there for a moment and licked her lips. Then she pulled down and stepped out of the rest of her clothes.

Seeing her naked before had been amazing. Poise and confidence and art. But art in museum, something roped off and untouchable. Now she was an offering, a beautiful sacrifice ready to be devoured.

I got up and took a moment to circle her slowly. She really was fascinating. This professional woman, this mother, this wild force of nature that had placed itself in his hands. I ran my fingers over the tattoo on her shoulder and she shivered. I lowered my hand to rest on her hip and kissed her shoulder. I pulled her skin into my mouth and teased it with my teeth. I worked my way over her shoulder around to her collarbone laying kisses as I went.

I traced the dragons tail between her breasts with with my fingers. Petting the beast. I went down on my knees and began following it with my mouth, working my way down between her legs. I could smell her desire and I couldn’t wait to taste it.

She widened her stance to give me better access and I followed the dragons tongue inside her. I looked up to her face and her eyes were closed, a look of abandon on her face. She held her hands interlocked behind her head. I licked along her lips and slid a finger inside her. I pulled her clit into my mouth and she started rocking her hips into me. With my other hand I reached up to her breast, kneading it in my hand. I pinched her nipple an she moaned softly. I pulled the finger inside her against her g-spot and felt her start to spasm. I dipped a second finger inside to wet it and then worked it inside her ass. With one hand she grabbed my hair and crushed my face into her, screaming into the other that she had plastered over her mouth to muffle the sound. She held me there, working her clit with tongue and teeth, my hand pistoning inside her. Finally she let me go, turning and bending over the couch, presenting herself to me. She looked back over her shoulder and begging me with her eye.

I got up, and noticed the other women for the first time since Karen and I had started. Jennifer was on the couch, her hand down her pants and working furiously. She was watching us with drowsy eyes, lost in her pleasure. Maxine had Sam head in her lap and was playing with her hair. Jackie had gone much further. She was naked, one hand at her mouth, a finger circling her lips, the other massaging her small breast.

Karen noticed her as well and motioned her over. She slid up behind me and pulled my shirt over my head. She reached around and undid my pants and pushed them down, finally releasing my aching dick. She gave it quick stroke but led me to where Karen waited, still looking over her shoulder. “Put it inside me.” she said and I did.

I went slowly at first, relishing in the spasms of her pussy, but I couldn’t hold back and started slamming into her, rocking her with every thrust. Jackie stayed behind me, rubbing my chest and arms. Finally I couldn’t hold out any longer and I exploded into her, pumping her full until my pace slowed and pulled out of her. Our combined juices coating my cock and dripping down her leg.

Jackie went to her knees in front of me, cleaning my cock with her mouth, sucking the sex from me. When she was done she went to Karen, who was still collapse over the couch, blissed out but utterly spent, and licked the cum from her thighs and between her legs lapping at it and sending further ripples of pleasure through Karen.

I was getting hard again, watching the way she cleaned the other girl with her tongue. Jackie crawled back to me then, and brought me back to full attention with her hands and mouth. She laid me down on my back and climbed on top of me. She rode me and clawed at my chest. She shuddered and spasmed around my cock, gritting her teeth and not making a sound outside the occasional grunt. She rode till I came and Wimpered as I softened inside of her. She collapsed on my chest, exhausted, my soft dick still inside her.

And I then I heard Karen say “Jennifer, Truth or Dare?”

“Dare.” Jennifer said in a husky voice.

“I Dare you to go get Jonathan back up so Jackie can finish, then sit on his face so he can return the favor.”

I turned my head and Jennifer was sliding down her jeans as she headed over to where Jackie and I lay on the floor. Jackie kissed me then and I lost sight of the younger girl. I felt her a second later, using her mouth to free my soft cock. Jackie moaned into my mouth and ground herself into my pelvic bone. Jennifer suckled me and gently massaged my balls. Slowly I began to stiffen, growing larger in her mouth. She kissed the tip, licked down my shaft, and ducked a ball into her mouth, caressing it with her tongue. She worked my cock with her hand, made slick with all the spit and cum. She could tell I was ready and positioned my dick at Jackie’s entrance.

Jackie moaned again but pulled from our kiss. “My ass, stick him in my ass.” Jennifer realigned me and I could feel myself pressed against Jackie’s pucker for the half second it took her to steady herself and slam herself onto my cock, then I moaned as she started working me in and out of her. My moans were cut short as Jennifer lowered her shaved sex to my mouth. She was warm and delicious and her scent was intoxicating. I nibbled at her clit and sucked it into my mouth, but she wasn’t satisfied with the gentle caresses and she rotated her hips and ground herself into me. I drove my tongue into her pussy and swallowed so I wouldn’t choke on her juices.

In a way i was glad for the distraction. My cock was in heaven in Jackie’s ass. As best I could tell from my vantage point the two girls were kissing above me, Jennifer’s hand in Jackie’s cunt. Karen slid up besides me and began whispering in my ear. I can’t remember exactly what she said because I blacked out in ecstasy. I came to with Jackie’s mouth on my dick again, cleaning me. The others were dressed, with glasses of wine in their hands. Karen was at the center, appearing to be leading some sort of discussion. Jackie finished and led me to my clothes.

After I was dressed Karen came over to me and asked “Was that what you needed Jonathan? Was that how far you needed to go?” I wasn’t sure and I told her so.

“Don’t worry,” she said, “There’s always next week.”