Arranged dates: Part 1 [fantasy] [mf]

It all started almost two years ago. She was totally consumed by her book, leaving her with very little time or interest for anything else. We’ve always been strongly supportive of each other, and that time was no exception. As much as my libido was building up, I tried my best to not distract her with my needs. And while she was primarily focussed on her book, she took note of what was happening.

One day at breakfast she shared her idea.

“So I’ve been thinking about our situation and I have an idea. Why don’t you sleep with other women?”

“Uh…are you serious or messing with me?”

“I mean it. I see no harm in it. It’s not like cheating’. She quickly added with a smirk, ‘Heck, I could even hook you up with a friend.”

“Well, to be honest, I’m turned on by the idea. But I’m not sure if I can actually do it”

“OK, how about this — just go on a dinner date and see how that goes”

“OK, well, what the hell. Hook me up.”, I said with a feeling of mixed excitement and nervousness. Back then, I was nowhere as sexually or socially open as I’m now.

The same week, she briefed me up on the date.

“OK, so I have arranged dinner tonight for you with my friend, Samantha. We went to school together. I think you’ll enjoy her company”. “…and, just to make things easier for you, I’ve advised her to dress a little provocatively”, she added with mischief in her eyes.

“Oh god, I’m already nervous. I’m excited too, but more nervous.”

“Don’t worry, you’ll be fine. I know it. Play along and have fun”. “And, by the way”, she whispered into my ear, “Samantha wants to fuck.”

My jaw dropped. Once I recovered from this news, I started to get ready for my date.

—

**Hold it, please. Brief pause for some background**

Hi. Let me introduce you to my world. I’ve been happily married to my wife for 6 years. I’m very satisfied with and thankful for the relationship that we have cultivated. We enjoy many shared activities, support each other, and we don’t shy away from discussing ‘difficult’ topics. I’m now close to 40, and she is in her early 30s.

Almost two years ago, what started as an experiment has now become a lifestyle for us. My wife sends me on dates that she arranges for me, most of them with her close friends. It all started back when my wife had started writing her second book.

You might ask, why does she do it? My wife is a very unconventional and curious person. To the point that she does not see these games as taboo or breaking any codes, like most of us would. She does this to satiate her own curiosity, to get a unique window into how people behave, and to keep me sexually satisfied. Although we both enjoy sex with each other, that is not our primary mode of connection. We connect more cerebrally than physically.

And why do I do this? While I could get more sex by going out on my own and hooking up, I particularly enjoy this arrangement because of the kink factor. I’m a go-getter most of the times, but I also enjoy being pursued. It excites me to learn that my wife’s friends ask about me and request her to let them have me. And given how well she understand me, I trust her with how she sets up these playdates for me. These arranged encounters could vary from a dinner date lasting a few hours to a multi-day vacation in a different city. She is amazingly good with planning and attention to detail, and always sets up the greatest adventures for me and one of her chosen friends — and for herself. She likes me to recount my experience, and I suppose that her friends share their version.

One condition that she places is that we’re not to engage each other behind her back, and I’m happy to oblige. Not only do I not want to displease her and lose this wonderful privilege, I also find that this restriction make this arrangement hotter. For example, when she invites one of her friends over for lunch with us, we are not to discuss our past. Obviously, it’s known to all of us what we did, but not being able to overtly talk about it amps up the kinkiness.

You could say that in a way she’s my pimp, except that I don’t get paid for doing this. And neither does she, I suppose.

OK, now back to my date with Samantha.

—

**Date with Samantha**

There I was waiting at my table, waiting for Samantha, sipping a scotch.

“Hi, are you Brad?”

I looked up to find this blonde woman in her early 30s.

“Hi, yes, you must be Samantha. Have a seat, please”. “I apologize for being impolite, I already ordered myself a drink. I’m a little nervous”. I chose to be open and vulnerable, instead of projecting fake confidence.

“You’re fine, relax”, Karen said with a chuckle as she motioned me to scoot over and made herself comfortable right next to me. She was wearing a short black dress, a little immodest for this place, revealing her voluptuous figure. But I had already been warned about that.

As the evening progressed, I was getting increasingly turned on by Samantha’s assertive confidence. Samantha exuded sexual boldness and sophistication in the arts of seduction. Her low neckline offered a generous view of her ample cleavage. She kept sprinkling the conversation with physical contact— touching my arm, or pressing her thigh against mine just long enough for it to register as not being accidental.

“Shall we head out?”, she asked, lightly squeezing my arm, as she finished her second glass of wine.

“Uh…yeah”, I mumbled, trying to contain my bewilderment and lust.

“This was fun! Let me show you my place. I think you’ll enjoy the view”

She held my hand and was now leading me to her apartment, which was just a few blocks from the restaurant.

We walked into her cozy and tastefully decorated condo, in a high-rise tower. As I made myself comfortable, she put on some ambient music and lit a joint.

She motioned me towards her window, as if to show me something. She handed me the joint, and pointed out to something from the window. I stood there overlooking her shoulder, both looking at what she was pointing but also admiring this sexual being. The mix of alcohol, smoke, her sweet perfume, and the cool breeze from the window had made me feel relaxed and invigorated. She was babbling on something about the city, but I barely registered her words. It seemed obvious what she wanted, but she was playing it cool. Maybe she liked to tease, or she wanted me to initiate the play. I placed my right hand around her waist and planted a kiss on side of her neck, as I inhaled her sweet perfume.

“Oh my, I thought you’d just leave after the smoke”, she said as she lightly caressed my stubby beard with her palm.

By now, I was raging to pounce and unleash my pent on libido on her. I tightened my grip on her from behind with both my arms and pulled her into my chest, lifting her up from the ground. I pressed her into my body with a lot of force, pushing my crotch into her plump ass and nudging her neck with my face. I could here her light moans as I breathed down her neck.

I removed her dress in one quick motion, to reveal a fantastic curvaceous body underneath. She was well-toned with curves in right places. Haphazardly, I undid my belt and lowered my trousers. I turned her around and pushed her against the window and took a good look at her from behind, her plump ass yet to be released from her lacy thong and her beautiful shapely thighs.

I let out a loud sigh.

“Yes, play with me. I know you’ve been hungry”

I leaned on her from behind, while covering her shoulders with my arms. My raging cock, still within my briefs, was within inches of her ass. She turned her face towards me, as I gazed intently into her eyes for a brief moment. She leaned towards me and I latched on to her lips. As we continued to exchange wet slobbery kisses, I grabbed her waist with one arm and pulled her against my crotch.

My raging cock was trying to locate the right spot on her ass to press against, desperate to penetrate her. She was now pushing against me and grinding hard. Foreplay was over. I led her to the couch and had her lie on it facing down. Her left leg was touching the ground, while her right knee was resting on the couch. I asked her to extend her right leg a bit, and placed some cushions under her belly to push her butt out. Quickly undoing my shirt and briefs, I mounted her from behind.

I crushed her under my body weight, and pinned her left wrist. I lay there for a bit, resting on her, as I smelled her hair and rubbed my stubby beard on her jawline. Pulling her lacy thong to the side, I started to rub my cock along her pussy.

“Oh god, don’t tease me Brad. Fuck me now”

Supporting myself on my knee and hands, I glided my cock into her wet and tight pussy. She immediately clenched on my cock, as I kept thrusting. I began with slow and long thrusts, pulling the full length on the cock in and out each time.

“You like this new pussy? She wants to be friends with your big cock”

“Mmm hmm, I do”, I muttered as I began changing the pace. I placed my palms on her shoulder blades, locked my elbows, and raised myself. With her pressed into the couch under my weight, I started rapid dive-bombing on her. Each thrust would pound her with my weight, pressing her into the couch. She continued to push her butt out in order to receive each thrust with maximum impact.

Her body would quiver and struggle under my weight as she orgasmed. “Oh…God…Brad”. I could barely hear her words over the sound of my flesh slapping against hers.

After a few minutes of this intense workout, I lowered myself on her back and relaxed my arms. I reached under her and inserted my palms into her tiny bra and fondled with her firm boobs, as we caught our breath before the next round.

“I want you to ride me now”

We switched positions and she straddled me. She inserted my cock in her, and leaned forward to place one palm on my chest while pinning my arms behind my head with the other hand. She began with some deep movements, running her pussy through the length of my cock right from the base to the tip. I craned my neck forward to suck her nipples as her boobs bounced in front of my face. As she amped up the pace, I forced my hands free and wrapped them around her waist and pulled her forward. I squished her boobs against my chest and kissed her, as she continued to fuck my cock. “Aaah”, she moaned as she had another orgasm.

I flipped her over to her side. Standing at the edge of the couch, I placed my right knee on the couch and penetrated her. I raised her left leg above my shoulder and leaned closer into her body. I leveraged myself against the couch and her body, and began to thrust in and out. I glanced below at her and noticed that her wet asshole was glistening with sweat and her juices. Sensing that I was nearing a climax, I increased the pace. Each thrust sent ripples of sensation through my body. Almost at the point of cumming, I was now doing frenzied shallow thrusts.

“Yes yes yes, cum in me”

My legs and back contracted, and I released my sap into her in waves. Ripples of ecstasy pulsed through my now relaxed body.

I leaned on her to rest for a bit, before getting up to get ready.

“Tell Karen I said thank you. I’d like to play with you again, with her permission.”

*To be continued….*

Source: reddit.com/r/sexystories/comments/92pj2g/arranged_dates_part_1_fantasy_mf