I bought my first house when I was 26 years old. My neighbors were Jennifer and John, a couple about twice my age. Being older, my manners taught me to call them Mr. and Mrs., by their last name, until they insisted Jennifer and John was fine. I could tell John was a lot older than Jennifer. We had a low fence dividing our yards with hedges on both sides of the fence, but we could each pier over, if we really wanted to see into the other’s back yard. We often made small talk over the fence. John was pleasant but reserved. Never had too much to say. Just “hello, how’s it goin,’ nice day, catch you later” sort of stuff. I usually saw him leaving or coming home from work. He worked Monday through Friday and my days off at the time were Tuesdays and Wednesdays.
Jennifer, on the other hand, was very friendly with me. She was a stay-at-home housewife. Oddly, although her name was Jennifer, she looked a lot like Courteney Cox. She was tall, about 5′ 10, black hair, slender, shapely body, long legs, pretty face, green eyes, and a great, warm smile. Her fingernails were at all times manicured, usually an enticing red or burgundy color. I guessed her to be about 45. She was often barefoot, pretty feet with painted toenails that matched her fingernails. She worked out at a nearby gym and kept herself in great shape. Even though she was a lot older than me, a very attractive and sexy woman. I would often see Jennifer laying out in a bikini or short-shorts and a halter top in their backyard, suntanning, especially on my days off. She would be reading or playing on her phone. I “conveniently” at all times made sure I had some yardwork to do when I saw her outside. I did my fair distribute of trying to innocently peek over the fence. I could have been imagining it, but Jennifer seemed to like seeing me and would often come over to the fence to strike up a conversation. I at all times had an erection seeing Jennifer laying out or when we talked over the fence. I wondered I even saw her glancing down there at me on more than one occasion, checking out the bulge in my pants.
One Tuesday, after John had gone to work, Jennifer was outside again, lounging in shorts and a tee-shirt, barefoot, looking great as usual. She came to the fence to chat. Noticeably, she was without a bra. I could see her nipples protruding through her shirt. She said to me, “Tommy, would you mind coming over for a bit? I’d like to talk to you about something.”
“Sure, Jennifer. Be right over.” I locked up the house and headed over. I rang the bell.
Jennifer called out, “It’s open, Tommy. Please come in. I’m in the kitchen.”
It was the first time I was in their house. Jennifer kept a very neat, clean house, apparently with a flair for decorating too. I found her in the kitchen and complimented her on how nice her—their—house looked.
“Thank you. Would you like coffee?”
“Sure. Cream and sugar, please.”
She got our coffee’s and we sat at her kitchen table together. I placed my hand in my lap to cover the growing bulge in my pants.
She started in, “Tommy, I have something very serious I’d like to discuss with you. I must have your complete trust. This must remain private, only between you and me. My husband must never know about this. Can I trust you?”
“Yes, of course,” I said, wondering what this was all about.
“Please don’t judge me. Hear me out before you say anything.”
I assured her I would.
“John and I have been married for 10 years. It’s s second marriage for both of us. I’m 51. John is 64. Our kids are grown and moved out. Honestly, we have a very good marriage, and I don’t want that to change. I love John, very much. I would never cheat on him. I won’t be unfaithful to him. I would never want to hurt him. He’s a wonderful man. But due to medical issues, John is impotent. It’s been over 4 years. We’ve tried things but he can no longer perform sexually. He won’t even discuss it anymore. He feels emasculated. I still suck my husband’s limp penis just to show him how much I love him. He does give me oral, but I feel like I’m pressuring him to do it. All that said, I still have fantasies and I have a high libido. I’m a voyeur and an exhibitionist. I like to watch and be watched. The one thing I really miss isn’t the intercourse, but it’s SEEING a man’s hard cock. And I want to watch a man masturbate. Neither of my husband’s would ever do that for me. What I’m asking, Tommy, is for you to be my mutual masturbation partner. We’ll both masturbate together. No touching each other. That would feel like cheating. There may not be a difference to some people but pleasuring ourselves isn’t cheating to me. My husband’s penis, 4 years ago, will be the last one to ever penetrate me.
You do like girls—women—don’t you, Tommy? Do I have your interest so far?”
I gulped. “Ummm, I’m not sure what to say. I’ve never done anything like this. Of course, I love women and I don’t have a current girlfriend. But yes, Jennifer, I can’t believe a beautiful woman like you would ask me to do this.”
“Good. It would be on your days off and my husband is at work. We could do it here. We can watch each other, dirty talk, tell each other our fetishes and fantasies, maybe watch some porn. I’ll do and show you anything you want to see. You can get as close as you want to my body and examine me. Just no touching. I just want to see you naked, with a hard-on. And try to maintain the hard-on throughout the session, however long it lasts. I can help talk you through masturbating. Do you ever watch porn or girls on webcams?”
“Well, yes, a little,” I said, trying to act innocent about doing that.
“Think of me as your webcam girl, only in person for you. I know I’m not a 20 something hardbody like you probably date, but I do try to keep myself in shape.”
“Jennifer, I’ve never been able to tell you this, but I think you’re so beautiful. You know how I always stare at you in the backyard. I just could never say anything to you before. I hope it’s ok that I said it now.”
“Of course, it is. And that’s the kind of honest talk I want us to have when we’re masturbating together. To hear you say you like my body will help me reach orgasms.”
“So, what do we do now,” I thought to myself. I didn’t have to wait long to understand.
“Tommy, I must remind you, my husband can never find out about this. It would hurt him terribly and ruin our marriage. He’s a good husband, a good man and a good provider.”
“I understand, Jennifer. I’d be embarrassed too, if he found out I was doing this, you know, jacking-off for his wife.”
“Well, today’s Tuesday. And you’re here now. Let’s try a little something simple right now and we’ll plan a longer session for tomorrow. Can you take all your clothes off for me, Tommy?”
“Wow,” I wondered to myself. She’s not shy about asking for what she wants!
“Ummm…,” I delayed and stuttered. “Are you sure this will be ok, Jennifer?”
“Tommy, I just told you what I want. We’re alone. You’re in my house. We’re adults. It’s not cheating, just masturbation. If you don’t want to do this, it’s okay. You can go and we’ll pretend this conversation never happened.”
She sipped her coffee and looked at me, waiting for me to respond. Nervously, I stood up and took my shirt off as Jennifer watched me begin to undress.
“Don’t be embarrassed. You look great, Tommy. Now, your pants, shoes and socks, please.”
I took my clothes and placed them on another chair next to me. I was nearly naked, only in my briefs, with a boner showing through my underpants, standing in front of this gorgeous 51 year old woman in her kitchen. She sipped her coffee as though this was perfectly natural.
She smiled and said, “It’s nice to see you’re hard already, Tommy. That’s the way I will always want to see you. Please take your underpants off and set them aside.”
I got nervous and embarrassed again, not sure if I should continue with this.
Jennifer’s tone turned firm and demanding, “Tommy, take your underpants off or go home. I won’t ask you a third time.”
I slipped my fingers into the waistband of my underpants and worked them down over my erect boner. As I was doing this, Jennifer brought out a towel and laid it on the kitchen floor in front of me. I knew what it was for. She knew I would leak. I was now completely naked. I tried to cover myself. Jennifer seemed impressed with herself that she got me to undress for her. She had a slight smile and began cooing, muttering, “omg, omg.”
“Tommy don’t cover it. You look great. Your cock is wonderful, Sweetie! Your cock is so thick! And those nice big balls! My husband’s balls are much smaller. And his penis was smaller too. I love seeing you naked like this. Turn around so I can see your ass!”
I turned around and tightened my butt cheeks to make me look a little better, then turned back to face her again. I began to wonder if I was doing this alone or if Jennifer would undress, like she said she would.
She said, “To tell you the truth, I could get myself off just looking at your cock right now. It’s been so long since I’ve seen a man’s hard cock. But I promised you more. That this would be mutual masturbation. That I would show you my body, all of me, anything you want to see. But how about if I just show you my tits today? Save something for tomorrow.”
How could I argue with her. I was naked with a beautiful older woman staring at my hard-on. I consider myself average looking, and about average size, 6″, maybe 6 1/2 on my best days, but if Jennifer was telling me the truth, she hadn’t seen her husband’s hard cock, or anyone’s in over 4 years. And he never masturbated for her. And she said, he was smaller too, so that made me feel good about my size. Now I was going to get to see her tits, the one’s I’ve gawked at from over the fence. I’ve masturbated at home while fantasizing about Jennifer. Now I would see her—them—in person.
Jennifer continued, “My tits are kinda small. I’m a 34B. I hope that is okay for you. But my nipples do get very erect and hard, like little pebbles.” Jennifer pulled her tee-shirt up over her head and exposed her tits to me. She tucked her elbows into her sides to tighten her cleavage and shook her tiny body from side to side to make them jiggle. She didn’t have to do that for my benefit, although she did look sexy jiggling them. But they looked just fine to me, hanging down naturally, perfectly. They had a nice, natural, slightly saggy droop. She cupped them and held them out to me, as though she was offering them to me. She had tan lines from her bikini and her tits looked alabaster white compared to her darker tanned skin. Her nipples were about the size of quarters, dark and protruding. “Do you like them, Tommy?” She pulled her nipples and swirled her little tits in tiny circles. “I’m playing with my tits for you. Put your hand on your penis and stroke it for me. Tell me you like my little titties.”
“They’re gorgeous, Jennifer. Perfect little mounds, perfect mouthfuls. I wish I could suck on them.”
My comments made her smile bigger as she watched me fondle myself for her. She unbuttoned her shorts, unzipped them, and put a hand inside her pants. I could only see some bare skin around her hand, so it appeared she wasn’t wearing any panties. She started to moan and rock back and forth in her chair. “Please don’t cum yet, Tommy. I want to have an orgasm while I’m watching you. Can you “edge” when you feel close and stop? I think that’s what they call it.”
I was leaking pre-cum. A long strand dripped from my tip and finally fell onto the towel.
“Oh, Tommy, you’re so excited. I love to see your penis oozing like that for me!”
“I’ll try to edge, but I’m feeling very excited. This is an incredible feeling to be watching you and playing with myself like this.”
“I was sure you would like this and agree to my plan. I’ll be showing you my pussy tomorrow. Something to think about while you jack-off now, Tommy. I hope my pussy will excite you even more tomorrow. I love watching you jack-off while you’re looking at my tits. I’m glad they excite you. I’d like you to shave off your pubic hair for tomorrow. I want to be able to see all of gorgeous cock, completely bare, no hair around it. Will you do that for me, Tommy?”
I slowed up to prevent myself from cumming. “Oh my. Ok. Sure, I will do that.”
“That’s a good boy, Tommy. Keep touching yourself but now tell me a fantasy of yours.”
“Well, I love seeing your long legs when you’re outside tanning. I have a bit of a leg and foot fetish. I’ve seen you going out when you’re all dressed up, in a short skirt. You look great like that.”
Jennifer replied, “Would you like to see me like that tomorrow? Short skirt, black nylons, high heels? Would you like to look up my skirt? I have a great outfit I think you’ll love.”
I picked up my stroking. “Omg, Jennifer, yes, that would be so hot for me!” Jennifer moaned louder and increased her hand motion inside her shorts.
“I’m cumming, Tommy! As long as you don’t touch me, you can cum on my tits.”
I stepped up in front of Jennifer, and she spread her legs to allow me in close. She held her tits up for me.
I kept stroking, looking down at Jennifer’s pretty face and perky tits. “That’s nice, Tommy. That’s what I want to see. Pull your ball sack for me. Stretch your balls. Show me how much you love my tits. Jack your cock! Cum on my nipples.”
Her instructions, her exposed tits, made me cum. I shot several pearly ribbons of my cum onto her tits. She rubbed it in over her hard nipples. My knees nearly gave out and I had to back away before I collapsed on her body. I didn’t dare make contact with her or this would be over on my first day with her.
We both cleaned up, got dressed and Jennifer poured us a fresh coffee. We made some small talk, and I got up to leave. “11:00 tomorrow,” she reminded me. “Begin using the gate in the backyard. I don’t want any neighbors getting suspicious or saying anything to John. And remember to shave. And your balls too. I’ll wear something very special for you that I’m sure you’ll enjoy.”
The next day, Jennifer had her two recliners set up facing each other in the center of their room. Two towels were placed on the floor below them. There were pillows on the backs on both chairs. I assumed that was to push us up further in the seats. She met me wearing a long robe.
“Tommy,” she said, not wasting any time, “Take your clothes off and sit in one of the chairs. I’ll be down in a few minutes.”
I sat naked waiting for Jennifer to return. It seemed like forever, but only about 10 minutes later Jennifer began slowly descending the stairs in a slow sexy step by step fashion. My first reaction was an in-my-head, “omg.” Then I said it out loud. She was wearing a black push-up, half bra exposing her nipples and the top half of her tits! She held her arm across them, occasionally dropping her arm for me to get a better look, almost doing a striptease walking down the stairs, extending her legs and feet as she descended. Her black miniskirt was the shortest I’ve ever seen her in. Her long legs were encased in black sheer nylons ending in a pair of black stilettos “come-fuck-me” pumps, the kind with the red bottom soles. She was absolutely stunning! My cock instantly rose to the occasion. I was at full mast as she sauntered into the room. I sat up on the edge of my chair. My balls hung down over the edge.
“That’s perfect, Tommy! Looks like you’re happy to see me. I see you shaved. Very nice. Your shaft looks so big like this.”
“I’m very happy to see you, Jennifer. You look amazing!” I started to fondle myself. I knew she’d like seeing that.
Jennifer took a seat in the chair across from me. She crossed and uncrossed her legs several times, giving me a slight peek under her skirt. “Tommy, are you peeking up my skirt? Do you want to see my panties?” She didn’t wait for a response, she spread her legs, they touched the sides of the chair. I had a fantastic view right up her skirt! She crossed her legs, man style, with her right foot resting on her left knee. Her skirt crept up higher around her waist giving me an amazing view of her black, lace garter belt holding up her stockings and her sheer black, see-through panties. I could see the outline of her pussy through her panties and what appeared to be small landing strip patch of dark pubic hair above her vagina. She liked my staring at her genitals as she watched my hand manipulate my cock. She rocked her foot on her knee. She sat patiently, allowing me to look up her skirt. A wet spot appeared on her panties. Finally, she asked me, “Want more?”
“Oh, yes, Jennifer, please! Please take off your skirt and panties for me and let me look at your pussy.” She stood up, unzipped the back of her skirt and let it fall to the floor. She kicked it away. She looked magnificent! She wiggled out of her panties and tossed them along with her skirt out of sight. Jennifer sat back down in her chair, this time raising a leg over the sides of each armrest. She dangled a shoe off the toes of one foot, rocking it back and forth. She was wide open for my view now, dressed only in black accessories, the half-bra, stockings, garter belt and those perfectly matched heels! She had beautiful pussy lips that were glistening from her wetness.
“Do you like what you see? Show me you do. Pump your penis, Tommy.”
“Jennifer,” I started, “May I….I mean….could I…would it be okay to smell you? You know…down there?”
Jennifer laughed, “Tommy, you don’t have to be embarrassed to ask me for anything. I’m gonna ask you to do things that you’ll discover very embarrassing. But I promise you, you’ll enjoy our time together.
So, we already found a new fetish you have. You like to smell pussy? My naughty neighbor boy wants to smell my pussy and jack-off? I bet you’d love to smell my pussy after a hot day wearing pantyhose and panties all day. Come over here and get on your knees. Remember, no touching but you can get as close as you want and smell me.” Jennifer watched my head go between her spread legs. I inhaled deeply, taking in her powerful, womanly scent as I continued to massage my cock and balls. She ran her hands down to her pussy and gently opened herself up for me. So pink and inviting, yet I knew not to touch her or this would be over. I could only imagine if poor John ever saw what I was doing with his wife, smelling her pussy, looking at her spread, masturbating for this exciting, sexual goddess.
Jennifer said, “Smell me as long as you need to. I’m so hot!,” as she began to finger herself, guiding one, then two fingers into her open cunt. I watched her painted nails slip past her pussy lips and disappear inside of her. She used her other hand to stimulate her clitoris and we were both masturbating, watching each other. “Tommy, stand up and cum on my pussy! I want to feel you cum on me.” Jennifer rubbed faster and harder as we both moaned and groaned, and my cum spurted a large first glob over her masturbating fingers and dripped down into her pussy. She held herself open to receive my remaining several spurts which I was only too happy to give her. She fell back in the recliner, and I collapsed on the floor. I brought her a wet washcloth to clean up. Jennifer remained in her sexy little outfit and went to get us two lemonades. I got my first view of her sexy, little wiggly ass as she walked to the kitchen! Her heels clacked against the tile floor.
We both sat back in our chairs shipping our lemonades. My cock shriveled back down to limp. Jennifer said, “Let’s talk a little before you go, Tommy. First, I’d like it if you could refrain from masturbating from now until next Tuesday, when we meet again. I only want you masturbating when you’re naked and in front of me. Can you do that?”
“Yes, I’ll try.”
“You’ll try or you WILL?”
“You said you like feet. Mine are small, size 6 1/2 but I think they are pretty. She slipped off her shoes. Do you like them?”