My wife and I have been married for almost twenty years. We were married in our early thirties.
We first met when we were in the fourth grade. We went to school together until we each went to different high schools. She was a pretty plain girl and in spite of her getting her breasts in the fifth grade, hers much larger than any of the other girls, none of the boys paid her much attention.
Nineteen years had passed since then. A lot had changed in that time. I had spent years in the Marine Corps, been married, came back to the “hometown”, entered corporate life, gotten divorced and had been living alone for a couple years. I ran into DeeDee one day and I couldn’t believe my eyes. She certainly wasn’t that awkward girl I used to know.
She was a good looking, confident thirty-one-year-old woman. It was obvious from first look that her early start in puberty had served her well. She had a beautifully curvy body with great tits. I’d later find out after we were married that she was a 38DD. I asked her out and the rest is history, as they say.
Over our first few dates we did the typical, catching up on the years since we last knew each other. DeeDee was really interested in my military adventures and she even seemed to take an interest in my high school shenanigans. She was very empathetic and understanding about my divorce.
DeeDee, on the other hand, had a very different life experience. We went to private school through junior high. She then went to the public high school and really didn’t feel like she fit in. It was a big school and she made a few friends but wasn’t really social. She never had any boyfriends or even dated in high school. Come to find out, even since high school she had never gone on more than one date with a guy and only a couple of those.
DeeDee was working with the same company since high school and she was still living with her parents. Our experiences couldn’t have been any more different up to that point.
Our first kiss was on our fourth date and DeeDee says she still remembers it like it was yesterday. I have to admit, I don’t. It was her first time kissing a man, so I’m sure that has something to do with it and not that I was so great. As things progressed, I learned that her almost overpowering confidence completely disappeared when it came to her view of her body. I guess with her background that shouldn’t have surprised me, but given our different experiences, I had a hard time understanding it.
We’ve enjoyed a great sex life since before we were married, even though DeeDee has been a real puzzle in that regard. I knew she was a virgin. I didn’t initially realize how completely naive she was about sex. She was absolutely embarrassed the first time I slid my hand into her panties. She was so invitingly wet it felt like pure silk. She thought I’d be completely grossed out by her wetness.
One day we were talking about sex (before we had even had sex) and I mentioned doggy style. She was appalled and proclaimed she would never do that. I was in disbelief. What could possibly be the objection to that? As it turns out, she thought doggy style always meant anal. After an initial chuckle, I explained.
Since we’ve been married, we’d covered a lot of ground sexually and she’s really quite adventurous. DeeDee has a toy collection that would make Christian Grey jealous. She loves anal and often demands it. She’ll flash me in public for a pic or two when she knows she won’t be seen. On occasion, she’ll even ask for some rather serious BDSM. But through it all, she’s never thought of herself as desirable. No matter what I say or do, she is convinced I’m the only man who would ever be interested in her.
So, this has been our experience together. Every time I introduce something, her starting point is that it can’t possibly be something people really do or that it’s something so kinky “normal people” don’t really do it. And almost every time, once she tries it, she really enjoys it. In fact, she absolutely loves sex. I dare say she has a higher drive than I do.
But she has her hard “no’s” also. She’s really curious about strip clubs, but when I offer to take her it’s a no. Taunting her to flash a trucker, nope. Floating the idea of other people, hard “no”.
We’re fifty-two years old now. She’s put on a little weight, nothing outrageous, just the effects of time. The upside is her boobs are now 40DDD. The downside is it has made her insecurities and low opinion of herself even worse.
One day in June last year, my friend Dean called me during lunch. He was working a job on our side of town and wanted to know if I’d be around after work. He said he could stop by for a drink when he wrapped up the job. I’m always up for a cocktail, so agreed immediately.
Dean and I have been friends since our freshman year of high school. As long as I can remember, it was always Dean, Greg and me hanging out. We all went into the military after high school and when we all returned home, it was the three of us again like no time had passed.
Dean was a groomsman in our wedding. He surprised me a few years back when he shared some bedroom photos of his wife with me. I was in heaven. She’s a great looking gal; thin, firm perky breasts, and a great ass. Since then, we’ve shared quite a few pics of our wives. Dean has always had an eye for DeeDee and pics of her fantastic breasts and round ass always elicit comments.
The doorbell rang at about 6:00. Dean came in and kicked off his work boots. The usual small talk as we walked to the kitchen. DeeDee was in the kitchen, just putting away the last dishes from dinner. “Hi, Dean. How was your day?”
“Hey, DeeDee. Can’t complain. How are you doing?”, Dean responded.
“Not bad. Still trying to adjust to the working from home thing. What are you guys drinking tonight? I’ll get you set up.”
I looked at Dean to see if he had an opinion. “How about Bee’s Knees tonight? Seems like a good one for a summer night.” I knew he’d come up with a good one.
DeeDee grabbed the gin, glasses and shaker from the cabinet and set them on the counter. As she pulled the lemon juice and honey syrup from the fridge she commented, “You guys have fun,” put the last items on the counter, and went upstairs.
As I started mixing the drinks, Dean commented, “Always nice to see her at the end of work day.” I knew what was going through his mind. DeeDee’s t-shirts are all V-neck and display her cleavage quite nicely. Although she never notices, he always enjoys the view.
Dean and I headed out onto the deck. We talked for hours, occasionally taking a break to mix more drinks. It was a beautiful day that turned into the perfect early summer evening. As the sun dropped, the warm air cooled off nicely. I reached over and turned on the fire in the fire table that sits in the middle of our four deck chairs.
It must have been about 9:00 when the sliding door opened. DeeDee walked out and sat down in the chair across from me, setting her drink down on the table. “Am I interrupting guy talk?”
“Just BS’ing. You’re not interrupting anything,” I replied. I was a bit surprised. DeeDee doesn’t really drink. She may have a drink a couple times a year, but it’s unusual and generally goes straight to her head when she does.
“I just thought I’d stop down and chat a bit before bed.” She had changed into her comfy evening clothes, the ones she wears curled up on the couch for the last few hours of the day, so I knew she was winding down for the night. Her drink was half gone when she came out to the deck and she had been taking sips as we chatted.
The three of us sat there talking for a while. Dean was on his fourth cocktail and I could tell he was feeling pretty loose. I don’t remember how the conversation turned to it, but somehow, we started talking about foot rubs. I know, it sounds cliche. But that’s what happened. And before any of it even really registered with me, Dean got up from his chair, pulled the foot stool around to the other side of the fire table and sat on it in front of DeeDee. He reached down, picked up her foot and laid it in his lap.
DeeDee giggled at first. “You really don’t have to...” her sentence was cut off by a long moan as Dean pushed his thumbs into the bottom of her foot. Her eyes rolled as her head tilted back. The moan got deeper, “Oohhhh...”
“I thought you might like that,” he responded.
I was chuckling, still kind of unsure how we got to this point. What I thought was a quick bit of flirty fun went on for about five minutes. Dean and I kept talking. And DeeDee kept moaning her approval, eyes closed. He set her foot down and picked up the other one. Dean stopped talking and worked on her foot.
After a few minutes, he slid his hands up and started kneading her calf. DeeDee opened her eyes and looked over at me. It was a look of surprise, but also pure relaxation and something else I couldn’t quite figure out. It was a brief glance as her eyes rolled back again and she let out another moaning sigh.
As I sat there, unsure of what I was watching, DeeDee relaxed and slid down in the chair. Dean sat back a little bit, no longer having to reach for her calf. He switched over to her other calf and her contented moans continued. She took her other foot and moved it out of Dean’s lap and set it on the deck. Doing that spread her legs a little bit. Her evening shorts are pretty loose; and even though she wasn’t flashing anything, I knew that she never wears panties under them. Dean looked over to me with a grin.
It was perfectly quiet aside from the occasional moan from DeeDee. Dean continued his task and slowly his hands slid up to her thigh. I was certain we’d reached the end; that he was going to get slapped away. DeeDee let out a moan that was bit louder and couldn’t be mistaken for anything other than pure pleasure. As she did, she dropped even lower in the chair; her butt coming just about to the edge of the seat and her legs spreading even further, one laying in Dean’s lap and the other to his side.
At this point I could see she was flashing the side of her pussy. Dean noticed it as well, giving me a big grin. After years of seeing it in photos, I knew he was dying to get a real life view.
Dean’s hands slowly moved up DeeDee’s thigh. I was pretty surprised by his bold move and I waited for DeeDee to brush him aside. I was doubly surprised when his hand slid up the loose leg of her shorts and she responded with a loud, heavy breath. “Oooh, wowww…” was all she said.
She made a couple of quick, short, startled breaths. He must have been hitting her clit just right. Then I could hear the unmistakable sound of his fingers in her wet pussy. Her fingers tightened on the arm rest of the chair. She never even opened her eyes, but managed to utter, “Don’t tease a girl!”
I thought it was about time I interrupt and keep her from doing anything she’d regret. “Umm, hey, DeeDee…?” was all the farther I got.
She quickly cut me off. “Shush. Don’t wreck it!”
Dean looked over at me with what I could tell was a request for permission. I gave it a couple seconds of thought then nodded. He pulled his hand out from the leg of her shorts and reached up to the waistband with both hands. As he started to pull, DeeDee lifted her bottom off the chair just enough to let the shorts slide down. She picked up both feet, allowing the shorts to be removed completely and then put them back down one on either side of Dean sitting between her legs. And there she was.
In the warm glow of the fire, my wife, low in the chair, her beautiful bald pussy exposed and somewhat parted open and glistening from the attention of Dean’s fingers. At that point I was beyond surprised, completely caught off guard and amazed at what I was watching. But I’d be lying if I said I wasn’t turned on and loving what was unfolding. My shorts were betraying the full hard on inside. Never in my life would I have guessed this would happen.
Dean didn’t waste any time. He dropped her shorts, stood up and kicked the foot stool he had been sitting on to the side. He sat down on the deck right in front of her chair, eased each of her thighs onto his shoulders and buried his face right into her pussy. She immediately winced and gasped, then just settled into heavy breathing. He was taking his time with her, exploring every bit of her and she was responding in appreciation.
After a minute or so passed it finally dawned on me that my view at this point was pretty much the back of Dean’s head. I had been completely lost in the sight, trying to comprehend what was happening. I got up and slid my chair a few feet to the side so I could see better. Her pussy had opened up and Dean was running his tongue from the bottom up to her clit. Every time his tongue hit her clit she gasped.
As he ate her pussy, his hands worked their way up her belly. When he reached her bra, she reached in and lifted the cups from the bottom over her tits. Her heavy breasts fell free and he took one in each hand, squeezing their full roundness and playing with her hard nipples. Her large pink areolas contracted a bit in the cool air of the night. I was awestruck. My wife, tits to the sky with my best friend's face in her pussy.
Dean pulled his hands back and put one under each thigh. He lifted her legs and draped them over the arms of the chair. She was spread wide open. Both her pussy and his face glistened wet in the firelight. With her legs pulled up, her perfect pink asshole was exposed. Dean grabbed each butt cheek and held them, leaned in and started working her asshole with his tongue. DeeDee yelped and began to squirm. She loves having her rear end tongued. He slowly ran his tongue from her asshole all the way up to her clit. He’d pull back and do it again and again. She was in heaven. I just wondered if she’d even remember it.
He pulled away from her pussy and took a minute to absorb the sight in front of him. He moved his left hand up to the inside of her thigh. His thumb reached for her clit and began small rotations on it. DeeDee doesn’t usually tolerate direct pressure on her clit, but she seemed to be writhing with it. Dean slid his right thumb over and started firm round motions on her asshole.
I knew from experience he wasn’t going to find much resistance after eating her ass like that. Sure enough, every so often I could see his thumb slide into her ass just a bit. He continued for a minute or so, before DeeDee winced and pushed his hand from her clit. She had reached that point where the pressure crossed from pleasure to pain.
Dean pulled back and got up on his knees. He opened his jeans and pulled them down along with his boxers. His rock-hard cock sprung up like it had just been released from a cage. I had been wearing nylon shorts and I know mine was painfully cramped. His must have been killing him. He didn’t even look over at me. He was purely focused on my wife spread out in front of him. He laid the head of his cock on her puffy wet pussy.
With the slightest pressure, he eased the head between her lips but not into her. He rocked back and forth a few times and then slid the head of his cock between her lips from the bottom of her pussy all the way up to her clit. She moaned as the head hit her clit. He slid across her clit a few times before sliding his cock the full length back to the bottom. Dean traced that path on her pussy several times, each time with the accepting moan of pleasure from DeeDee.
The silence was broken, DeeDee gasping words I’d never imagined I’d hear her say. “It’s time! I need you inside me!”
It had been maybe fifteen minutes since this all started, but felt like hours, and I couldn’t believe what I was seeing. Dean put his thumb on his cock and slowly pushed it down deep between her puffy lips. The head disappeared and he leaned forward, slowly sliding into my wet and ready wife. I could tell he was in, her sigh gave it away.
That was quite honestly the hottest sight I’d ever seen in my life. Her audible approval was apparent, like she hadn’t had sex in years. Dean was slow and deliberate. He pulled back just about to the point of pulling out and then slid back in. The cycle repeated as he passionately made love to my wife. A ripple ran through DeeDee’s tits each time he made a full, deep stroke.
It seemed like ten minutes had passed when Dean slowly pulled out. His cock glowed wet in the firelight and her juices were running down over her asshole and between her butt cheeks. He lifted each of her legs off the arms of the chair. DeeDee opened her eyes for the first time and he took her hands.
He stood up, pulling her up out of the chair. On the way up, she lunged for his cock. Her aim was on target and she wrapped her mouth around it. As he continued to pull her up his cock slid out of her mouth.
“Turn around”, he commanded her. As she turned and faced the chair, he pushed on her back making it clear what he wanted. She followed the lead and bent forward leaning on the arms of the chair, her beautiful round ass pushed back towards him and her heavy tits hanging under her.
He dropped back down to his knees behind her. He reached up and spread her ass open. Dean pushed his face deep into her ass. After a while of his tongue darting over her asshole, he stood up, spit into his hand and rubbed it over the head of his still-wet cock. He parted her ass with one hand and guided his cock to her asshole with the other.
DeeDee made a low humming sound in anticipation. Dean pulled his hands away and grabbed her by the hips. He simultaneously leaned forward and pulled her back. I wished I had a better view. I know how hot it is to see her perfect asshole swallow the head of my cock.
Her tone became sharp and he paused both movements for a few seconds. “OK. Now…”, DeeDee said.
And with that, Dean slowly slid into my wife’s ass. He buried himself up to the balls. He pulled back and drove home again. DeeDee shifted to hard breathing again and she began to take control of the tempo, rocking forward and back. She picked up the pace. His balls hung low and I could hear them slapping against her pussy. Her tits were swinging in rhythm to their passion.
This was very different than before. He had been very slow and gentle before. But now… there’s no other way to say it, he was just plain fucking her ass; and she was controlling it. They both grunted every time he drove it in.
Both their breathing picked up, as did the sound of his balls slapping against her pussy. Suddenly, Dean pulled out. He grabbed his cock and with a couple short strokes he launched rope after rope of cum up her back and across her ass. When he was done cumming, he gave her bare ass a couple good slaps with his cock. It landed with a wet thump and the cum splashed out from underneath.
DeeDee turned around and fell limp into the chair. She reached up and pulled her bra back down over her tits. Her eyes were closed and she struggled to get her breathing under control. She looked spent. I couldn’t tell how much of it was the alcohol and how much was pure exhaustion. Dean bent over and pulled his jeans up. Without a word, he went back to his chair and sat down.
Neither of them said anything. I didn’t know what to say. My cock was just about ripping through my shorts, straining to get out. After a few moments of dead silence, DeeDee stood up, picked up her empty glass and walked back into the house; never saying a word.
Dean hung out for about a half hour after that. You can imagine what the conversation was about. He was cautious at first, finally asking me if he had gone too far. I assured him I was fine. It was the hottest thing I’d ever seen. How much DeeDee will remember or what she’ll say, that’s a different story.
It was getting close to 11:00. Dean grabbed his work boots and left around the side of the house. I turned off the fire, picked up our empty glasses and DeeDee’s shorts that she had left on the deck and went in the house. All the lights were off and the house was quiet. I set the glasses on the counter and headed up to the bedroom. DeeDee was in bed, fast asleep. As I got into bed, I could smell cum in the air. The memory of the night ran through my head for at least an hour before I fell asleep.
The next morning, I slept a little longer than usual and woke up to an empty bed. I put on the t-shirt and shorts from the night before and headed down stairs. DeeDee was in the kitchen finishing a bagel and a glass of orange juice. I wasn’t sure what to expect. She looked up as I turned the corner from the stairs. “Good morning, honey”, she smiled.
How do I read that? Did she remember any of it? “Good morning to you. You look good this morning.” She really did. I was rather surprised.
“Aw, thank you. That’s so sweet.”
I figured I’d better enter into this a bit cautiously. “I didn’t think I’d find you so chipper this morning.”
“Why would you say that?”
“Well… you don’t really drink.” I figured I’d go that route and not mention the rest of the evening, in case she really didn’t remember.
“What are you talking about?”
“The Bee’s Knees. It’s unusual for you to drink. I was just surprised you were drinking, and a drink with so much gin in it.”
DeeDee looked at me with a smile and a bit of a giggle. And then she said something that left me completely speechless and has changed our life forever. “You know me better than that. That was lemonade.”