Personal Ad-ventures

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
WillB
WillB
21 Followers

True to our agreement, neither of us talked about Mark again. It took a few weeks for Lori to get back to what I considered normal in her sex with me. Initially, she seemed awkward and reserved, but she eventually got over it. As for me, it was difficult not to flash on the image of her and Mark in bed, especially when Lori and I were making love. To be honest, though, the image was a stimulating one.

3

My next visit to the P. O. box yielded two letters addressed to "Occupant." One had been addressed using block letters, the other written in what appeared to be female longhand. Intrigued, I sat in my car and decided to open the printed one first, saving the best for last.

Dear Occupant:

I read your ad and both me and my wife are interested. We answered another ad a few months ago and got together with a woman who was bisexual. I enjoyed the hell out of it, but my wife wasn't all that excited. I don't know whether it was because I was having sex with this gal or whether my wife didn't dig having a chick eating her out. Anyway, my wife made me promise that some day I'd make it a threesome with another guy. I told her it sure as hell wasn't going to be some bisexual guy, cause I don't swing that way. We saw your ad and she insisted I get in touch with you. One thing though, she wants to see what you look like before we agree to do it. If that sounds OK with you, give me a call. I should be home after six each night. My name is Jack and my wife's name is Sherri. We're in our thirties and love to get it on!

Jack included his phone number.

The second letter was written on pale blue stationery, in a very attractive hand:

Hi:

My name is Sherri. My husband Jack and I saw your ad, and it sounded inviting! He's been bugging me for years to let him bring a man over to the house so we could have our own little orgy. I said sure, but he's never done it. I think he's a little chicken (ha ha). Not long ago we put our own ad in the paper, asking for a woman who'd like to join us. We only got one letter from a woman, the others were from guys. This girl came over and we had a great time. Don't tell him I told you this, but Jack only lasted in her about two seconds before he had to cum! It was the first time I've been with a woman, and it felt GREAT!! I think Jack got his nose a little out of joint. Anyway, I told Jack to write a letter to you, but I don't trust him to do it. So I'm writing instead. I'd REALLY like to meet you. Call me at 555-4727. If Jack answers, just ask for me, Sherri. Tell him you work at my office. Hope to hear from you soon (pant pant).

She added a P.S.:

If for some reason Jack chickens out, maybe we could get together sometime, just the two of us.

Interesting. Sherri sounded like a handful for poor old Jack. I was a little hesitant on this one. I had visions of ol' Jack flipping out when I was slipping the high hard one to the missus. And as for Sherri, it didn't sound like she was a stranger to fooling around on Jack. If I did decide to go ahead with it, I'd definitely wear a condom. No telling who she'd been playing hide-the-sausage with. I had gotten a trifle horny prior to opening the letters, anticipating what they contained. I decided to throw caution to the wind and give Jack/Sherri a call that night.

Fortunately, Sherri answered.

"Hi, Sherri?"

"Yes."

"My name is Bill. I got your letter today in response to an ad I put in the paper."

"Oh, yeah. Bill. So your name's not Occupant, huh?" A little titter (her restrained laugh, not her chest size).

"That's my last name."

"Oh, a sense of humor. I like that. Look, Jack's not home right now, if you're free to stop by. He won't be back for another two or three hours."

I wasn't horny enough to risk ol' Jack coming home and finding us doing the deed without him. "Okay, but I can only stay for a minute. I've got some paperwork to do at home for work tomorrow. What's your address?"

"It's 773 Oakmont Place, just off Riverside." She sounded disap-pointed.

"I should be there in about fifteen minutes."

"I'll be waiting."

I rang the doorbell and the door opened. Sherri was dressed in a see-through negligee, and I do mean see-through. Her protruding nipples on very large tits and a small patch of dark pubic hair were as plain as if the material was plastic wrap. Her hair was a very light blonde, undoubtedly bleached, considering the darker color of her pussy and the telltale roots on her head. She had to have been closer to her forties than her thirties, as Jack had described. Still and all, she had a beautiful face with hazel eyes, and her body was in excellent shape. She reminded me of a showgirl whose age was sneaking up on her. Twenty, even ten years ago, she could have had her choice of suitors. Myself included. I was getting a woody just standing there.

Sherri invited me in and offered me a drink. I accepted a Stoly on the rocks. Seated on the couch, I was handed the drink as she sat down next to me.

"Uh, Sherri, thought you'd like to know, Jack did send me a letter. Got it today along with yours."

"Huh, that surprises me. Let's see it."

"I, uh, left it at home. It just says that you and he had an interest in getting together with me. He mentioned the girl you had over, and said he'd promised to find a man to join you guys. He also said you wanted to check me out before we agreed to anything."

"Talk about half truths. Well, I'm glad he had the balls to write the letter, anyway. Before you even ask, yes, I think you're acceptable—to put it mildly." She leaned over and kissed me, her tongue entering my mouth. Her hand went to my lap, glomming onto my semi-boner. "Mmmm, nice."

"Look, uh, Sherri, I'd love to stay for awhile, but I've really got to get home and get back to work."

"Unless I'm sadly mistaken," she said as she began to unzip my fly, "this won't take very long. Lay back."

I stretched out on the couch and she assumed a position on her knees beside it. She unbuckled my belt and opened the clasp on my pants, then pushed them down to my knees. My cock was at attention.

"Here," she said, opening her negligee and hefting one of her tits. "Something to keep you busy while I'm working."

As her mouth slipped over my shaft, I fondled her breasts. They were firm, firmer than they would have been without the silicone. Her nipples were responsive, and hardened right up under my caresses.

In a matter of seconds I came to the realization that this woman was very talented. She was doing magic on me like I've never felt before. I can't say exactly what she was doing, but her mouth and lips and tongue and even her teeth were playing me like a flute. My ass was wriggling on the cushion and my lower lip was caught between my teeth. If this were a contest to see who could bring a man off the fastest, Sherri had no equal. A minute after she started on me I was ready to explode.

I wanted to prolong the pleasure a little, so I tried to think about stock options and changing the oil in my car. She did something else, like a combination of a sucking action and a light grip on the head with her lips and teeth, and that was all she wrote. The final out of the game. The cows had come home. The fat lady was singing.

She siphoned every drop from my cock to my balls and back again, and once I was drained she sent it all to her stomach with an audible gulp. Bar none, that was the best blowjob I'd ever hope to have.

She was right. Five minutes after she started pulling on my zipper, I was pulling it back up. I tried to chugalug my drink, still worried that ol' Jack might come bounding in the door any second. I remember thinking, If her blowjobs are any indication, I wonder what marvels she can perform with my dick in her? She could probably milk it like a farmer.

"Sherri, you know, I'm kinda worried about how Jack is going to react when we get together, the three of us. I'm not real sure it would be a good idea to go ahead with it. Sorry, but that's how I see it."

"You know, you're probably right. He can be a little overbearing sometimes. Hey, I'd be happy just to have you for myself. Fuck Jack! No reason you and I can't have some fun. Right?"

"Uh, yeah. No reason I can think of."

"Next time we get together, I've got a little something I'll bet you've never experienced before." She winked and grinned. She really was a very beautiful woman.

"It's a date. Can I call you here?" I still hadn't totally convinced myself this was a wise move, but she had certainly motivated me.

"Sure. Jack's usually gone until late on Tuesdays and Thursdays, so why don't you call some Tuesday evening and we can get together either then or on Thursday. Look, I'll tell Jack you called tonight, and after we talked you decided that maybe it wasn't really a good idea. You know, cold feet or whatever."

"Sounds reasonable to me. By the way, you give outstanding head. You oughta get a patent on your technique. It was, well, incredible!" I got up from the couch and headed for the door. I paused and gave her a peck on the lips, which she converted to an open-mouthed assault. I had to tear myself away, both in fear of Jack and of what I might be tempted to do, once my reproductive gear had a chance to recuperate.

"I'll call you."

* * *

I'm going to skip ahead for a while, but I'll go back to the proper chronology afterwards. I wanted to tell you what Sherri had in store for me on our next get-together.

I had followed her instructions and called her one Tuesday evening. I went over there that night, impatient as I was to see what delights awaited me. As soon as the door opened, Sherri was on me. This time she was stark-ass naked. I could barely get the door closed behind me. That would have given the neighbors something to talk about.

"Ooh, I've missed you," she purred, leading me by the hand to the couch. "Be right back."

I watched her trotting out to the kitchen, admiring her firm, rounded bottom and legs. She was wearing heels, which complimented her flawless legs. Not a trace of cellulite. Except for minor age lines about her eyes and mouth, Sherri could still wow them on stage, if that's what she used to do. What a package.

She returned with my drink and sat down.

"I've got a surprise. Jack is out of town and won't be back all night! If you can, I'd love for you to spend the night with me. It'll be wild!"

Her exuberance was endearing, but I did have a wife to contend with.

"Look, sweetheart, I'd love to, but in case you haven't noticed . . ." I held up my left hand to display my wedding band.

"Oh, I noticed. First thing. But I thought maybe you . . . Oh, that's okay. As long as you promise me sometime we can spend the night. You ever go out of town on business?"

"Yeah, once in a while."

"I don't mean to seem pushy, but it would be fantastic if I could go to wherever you're staying and we could, well, you know."

"I'll keep that in mind." I saw her face drop a little. "I mean it, I think that would be fantastic. Just you and me, all night. That is if my poor body can take the punishment." I grinned at her. She seemed to brighten.

"Lets get you out of those suffocating clothes." She started to work on the buttons of my shirt.

"Any objections to maybe using a bed this time?" I suggested.

"That was my plan, lover, I just hadn't gotten that far yet. This way." She pulled me up by the hand and led me down the hall to a spacious master bedroom. The bed was king-sized, with the corner of the covers already pulled down. After my clothing was hung over a nearby chair, I joined her in bed. She was lying there, affecting a provocative pose, her hair splayed out on the dark blue pillow, her arm over her head, her breasts in full view, and one leg drawn up and bent over the other to conceal her lower assets.

We warmed up in the traditional way, kissing and feeling each other from head to toe. Once she appeared to be responding, I put a hand on each of her knees, parting them and laying bare her glistening pussy.

"Time to repay you for the other night." I began by softly running my fingers over her belly and thighs, pausing to lightly kiss these areas as my fingers passed over. Then I started to gently nibble and lick the inside of her thighs, gradually nearing the primary target. I didn't kiss, or even touch her there, but instead blew warm air softly all over it. At one point I placed my open mouth over her clitoris and labia, exhaling hot air directly over them. Then it was tongue time.

My hands went to her breasts as my tongue began to lightly lick at her pussy. She moaned as I teased her clit with just the barest tip of my tongue. I separated her cunt lips with my tongue, running it up and down the crevice from her ass to her clit. My tongue darted inside the tight hole of her honey pot, evoking another moan. I returned to her clit, licking and sucking on the swollen button. I ever so slowly inserted the middle finger of my left hand inside of her, never pausing in my oral ministrations to her clit. I located her G-spot and gently prodded and massaged the area with the end of my finger. Sherri was undulating her hips, her low murmurs now almost continual.

I softly nibbled at her clit, while fucking her with my finger. She was getting closer to climaxing. I then went to my sure-fire technique, butterfly flicks rapidly applied to her clit, my finger slurping around in her tight, gooey hole. I twisted my hand around and found her asshole with my left thumb, wet from her vaginal secretions, and inserted it to the first knuckle. I had a grip on her like a bowling ball. The sounds from her mouth seemed to originate from deep within.

"Nnnuh, nnnuh, nnnuh." These guttural utterances, signaling her imminent release, struck me right in the balls. She was such a sexy woman, and the sounds she was making as I was making her come, turned me on something fierce. Odd as it sounds, I nearly came just listening to her coming.

The throaty grunts instantly became loud squeals and groans, as her ass bucked and gyrated under my mouth. She came in spades, nearly throwing me off of her. Her hands gripped my head, holding me tight to her convulsing cunt. It took her a full two minutes before her body relaxed and she settled back onto the bed. I've never seen such an outpouring from a woman's pussy before, so thick and sweet and abundant. My God, what a sexy woman!

I rolled over onto my back, fully expecting her to reward me with a little head.

"Not yet, lover. Later. I don't know when you're planning on leaving, and I don't know how fast you can recover, so I'm gonna assume this'll be a one-shot deal. I need some fucking first, lover, then I'm gonna curl your toes!" With that, she swung her leg over me, grabbed my boner and guided it into her. She settled down on me, as I slipped in easily. She began slowly at first, wiggling her butt around in small circles, at the same time lifting up then sitting down. Her head was back, her mouth open and her eyes closed, as she rode me like a corkscrew. I massaged her breasts, then pulled her toward me so I could put the nipples in my mouth. She continued to move her butt up and down, as I sucked then bit her nipples. She started the low moaning again, and in moments she spasmed through an orgasm.

Sherri was so tight, I couldn't believe that a woman of her age could be so snug. She was milking me. I don't think a man could grip as tightly as her cunt walls were doing. Yet it was so slick, I moved smoothly within her. It was also very stimulating. I flipped her over so I could continue in the missionary position, my personal favorite. I lifted her legs up over my shoulders, which I knew would hit her in just the right spot. I fucked harder, bringing her off in seconds. Then another. And another. She was nearly hysterical. I didn't back off until I felt myself getting close. She sensed it.

"No, no! Don't you dare come! Not yet! Just give me a little more first."

I did my best. She fired off two more before she stopped responding. She put me onto my back.

"You just lay there. I'm in the driver's seat from here on out."

Sherri sat up and opened the drawer of the nightstand, taking out two items. One was a tube of K-Y, the other was a slender white rope. Silk, I think. There were a number of knots in it, spaced maybe three inches apart. She uncapped the lubricating gel and squeezed some out into the palm of one hand. She then took the rope and applied the K-Y to it, from one end to the other. Next she pushed my legs apart. With a dab of gel on her finger, she stuck it up my ass.

I didn't know what the hell she was doing. She began feeding one end of the rope into me, pressing it in with her finger, a few inches at a time. I couldn't see down there, but it felt like she had stuffed the entire two-foot rope up my ass. Not used to having my butt messed with, it was a very tight fit. With my legs still bent and parted, Sherri began giving me head.

She cradled my balls in one hand, using the other to stroke my shaft while her mouth played my organ. It was another masterful performance. I gave myself two minutes at the most. A man can only endure just so much. I forgot about the rope.

"Let me know when you're just about to come. It's important. You gotta let me know."

"Oh, God. Believe me, I will."

It seemed like only seconds later and I was announcing it.

She continued to suck on me, deep-throating it so the head was practically touching her Adam's apple from the inside. I began to moan and my legs started to shake. I suddenly was reminded of the rope.

Sherri pulled on it very slowly but steadily. As the first knot popped out, I began to come. The sensation was incredible. Then another knot, and I shot some more. "Oh, Jesus Christ!" One after another, the knots popped through my tightly constricted asshole, each time inciting a fire in my loins that was sweet agony. Very unlike me, I bellowed loudly, the intensity nearly unbearable. I fired an explosive shot again and again. I thought I was going to blow the back of her head off. The come was running out of her mouth, down my cock, as she kept on sucking and I kept on shooting. "Oh, fuck!" As the last knot came out, I don't know whether it was liquid or just hot air that I spurted into her throat. It had taken a full minute for me to finish coming. That was as close as I've ever come to dying. Or so it seemed at the time. I knew there would never, ever be a more intense orgasm in my entire life. Sherri now possessed my soul.

"My God," I finally managed to say, "I think I'm in love."

She laughed and kissed me. "That's what they all say. Pretty terrific, huh?"

"There's not a superlative in any language that could describe it. It was . . . fan-fucking-tastic!

She giggled with self-satisfaction, absolutely radiating with glee. She had given me the thrill of my life, and she was the one gushing all over. I pulled her to me and kissed her, then held her very close. I had to be careful. Sometimes the heart and the hard-on are closely connected. I felt such an outpouring of love in me, but I had to tell myself over and over again that it was sex, nothing but.

I did make a promise to myself that night before I went home: The next trip out of town was going to include her, even if I had to fly her there.

4

After the letters from Jack and Sherri, it was almost a week before I got another one. My fingers were trembling as I tore open the envelope.

Dear Occupant:

Hi. My name is Susan. My husband, Marty, asked me to write this. He's watching over my shoulder as I write it. We saw your ad, obviously. We've answered this kind of ad before, and been pretty much turned off by some of the creeps that have shown up at our place. If that happens to describe you, sorry about that. Once in a while the guy will be surprisingly good. Not often enough though. Marty and I started doing this several years ago, having another man fuck me while Marty watches. I don't know which of us gets turned on more, Marty by watching, or me by getting fucked. As you can see, I tell it like it is. Do you like women to talk dirty? Anyway, one other thing I should mention. Marty's not really a homosexual, but he really gets off on going down on me right after the other guy comes in me. Believe me, he's not going to try to hit on you. He just wants to taste me with your come oozing out. Christ, Marty's trying to rape me right here while I'm writing this. I suppose you'd like to know what we look like. I'm 5-5, 120, with reddish brown hair and green eyes. Marty is 6-1, 180, with short brown hair and brown eyes. The things that turn me on are: men who like to eat pussy, getting spanked while I'm getting fucked (ooh, I really dig that!), talking dirty to me while you're in me, and watching dirty movies and getting eaten at the same time. We've got quite a few movies, if that turns you on too. Well, I think that covers it. Give us a call at 555-2089.

WillB
WillB
21 Followers