Craigslist

I’d tried to find adventure several times on Craigslist and got soundly burned. Most ads were some bot trying to get to sign up to a porn or a dating sight. However, every once in a while, since then, I click the link to see what’s there.

This one time, I noticed an ad which was oddly constructed, spelling askew, just one long sentence. The long and short of it seemed to indicate a couple of newbies offering “anonymous sex with the wife”. I couldn’t stop thinking about the ad. I wasn't looking for anything long term. Good sex was enough. Later that night, I replied with a seldom used email address. About 1 AM, my smart phone buzzed. “Jennie and Max” were responding. I wasn’t convinced. I asked for photos, a cell phone number and an address. The pics looked legitimate, the address was in a better part of town and the cell phone worked. We texted back and forth for over an hour, chatting and exchanging photos – no head shots, of course. Finally, we agreed to meet the next afternoon – Sunday. No way was I wandering into someone’s house at night.

Their instructions were specific: 3 PM sharp, knock on the door, not ring the doorbell, enter silently and put on a mask I would find near the door. A note would provide further instructions.

I arrived 5 minutes early. When I knocked on the door, it slowly swung open. As I closed the door behind me and locked it, I noticed on a side table both a black ¾ mask and an envelope with my name on it. Inside the envelope were my instructions. I put on the mask and took three steps down the hallway until I noticed Jennie.

She was lying on the dining room table, naked except for a duplicate of the black mask. The instructions were clear – no talking, no removing masks, immediate stoppage if Jennie said “stop”. On the serving cart beside the table were chocolate syrup, whipped cream, several wooden clothes pins, a 45-cm plastic ruler and a large, penis-shaped dildo complete with butt plug! I thought I noticed movement then. I looked up and there was Max, similarly masked and naked, sitting in the corner of the room with a movie camera. He was already excited and I hoped he had no designs on me. I had no designs either on him or on chocolate sauce. My instructions were to dress and leave right after I was done. Chocolate sauce would complicate my leaving.

I stripped down and moved toward Jeannie. She was about 45-50, in fairly good shape in spite of a hint of stretch marks, with average C-cups and dark, erect nipples and a neatly trimmed bush atop fleshy labia. I ran my hands over her feet and she jerked in reaction. My hands continued up her leg, to her thighs and hips and up again, over her belly and ribcage to her tits. I dawdled there for a while, caressing her tits, squeezing her nipples, watching her move silently with pleasure. Clothes pins! I attached one to one nipple, a second to the other nipple. She bit her lower lip but never made a sound. I trailed the third pin down her belly, across her bush and look one labia in my fingers. Ever so gently, the clothes pin grabbed her pussy lip. Within a minute, each nipple was captured by a pin and each pussy lip sported two more.

I took her legs and placed her feet flat on the table top, knees bent and splayed as far apart as they could go. With a little spittle on my finger, I found her clit. My finger rubbed back and forth, over the clit, into her pussy. She moaned each time my finger entered her. Then I remembered the dildo. It needed no lubrication. She was wet and I watched as it disappeared into her cunt. As the giant rubber cock entered and exited her vagina, one by one, I removed the clothes pins, starting with those on her pussy lips, then her nipples. Then I noticed the plastic ruler. I gave a tentative slap to one breast, then a second, finally a third, harder than the other two. Now, I’m not into pain, but she was. The ruler traveled up and down her body for several minutes, always flat side down, reddening the skin on breasts, belly, thighs, ass and pussy lips.

She may have been enjoying this, but there wasn’t much for me in all this, so I placed my arm behind her knees and pushed them toward her chest. Asshole and pussy, well exposed!

Obviously now, I could use the double-headed dildo to its full purpose. I filled both openings at the same time. Jennie moaned again – there was no doubt it indicated pleasure. Max moved in again, taking POV close-ups of the pleasurable intrusion. 15 minutes since I walked in the door and still not a word had been spoken. Jennie’s fingers moved to her clit. I helped her along with the vibrating dildo in one hand, the other hand roaming over and caressing her tits. She came strongly, urgently, loudly. The orgasm backed off somewhat but, moments later, renewed, as powerful as the first.

As a half hour approached, I was getting rather excited and hard. I thought to myself, “She enjoys being penetrated. Why not get a bit of enjoyment myself?” I pulled out the dildo, placed my hands on her hips and pulled her to the edge of the table. With her lower limbs on my shoulder, I moved, cock in hand, toward her gaping vagina. Max moved in again with camera in one hand, the other on his own erection. I rubbed the tip of my cock up and down her labia and over her clit several times. Then I slowly pushed in. No need for great effort. She was dripping wet. The alignment of my cock and her vagina allowed me to penetrate deeply. I plunged again and again, her cunt making sucking sounds as I moved in and out. Jennie moaned. Max chuckled to himself and continued filming. Then he moved to the top of the table, pulled his wife toward his side of it and entered her mouth.

We fucked in union for several minutes, Max in Jeannie’s mouth, my cock in and out of her cunt. Then I heard Max grunt. Cum leaked out of his wife’s mouth and squirted across her face. About then, I realized that I too was about to come. I moved slowly in and out a few more times, making certain her cunt squeezed my cock. Finally, as the glands butted up against her cervix, I came. Three or four more pushes to empty my balls… I stayed inside her then and motioned for Max to come with his camera. Once he was in place, I slowly pulled my cock out of her pussy. Sticky liquid oozed out along the length of my erection. As the last of it exited, the mouth of her pussy filled with cum. Max adjusted for his close-up – the money shot.

Jennie lay there, obviously satiated. Whipped cream, anyone? A spoonful on her lips, another on one breast, a third on the second breast, a fourth on her clit…and while my erection subsided, my mouth followed the sweetness of the cream to her clit where I spent a few more minutes, evoking a third orgasm for my silent partner.

Max had retreated back to his corner of the room. Jennie lay motionless and breathing hard on the table, one hand on one breast, legs askew. I used Kleenex to clean myself up and got dressed. I ran my hands over Jeannie’s naked body one last time and planted a kiss on her mouth. A quick nod to Max and I left.

Maybe, just maybe, I’ll check into Craigslist from time to time.