Stories by Cuckytoher
Cuckold Story: The Grocery Store
Was it me or was that woman in the grocery store aisle looking at me and snickering? I’m always paranoid when I venture out in public, even though at first glance I appear to be a seemingly normal male doing some shopping, short in stature, bald head, pale and a bit pudgy, it’s what’s beneath my clothes that keeps me wondering. Today I’m wearing a pair of pink tights and a pink strapless bra that my wife Katie insists I wear whenever I go out shopping for them. Them being her and her lover Reggie, who are now home lounging around on the overstuffed couches watching Good Morning America. The woman moves down the aisle and I am momentarily relieved.
You see Katie and Reggie’s friends know who I am, and all about our lifestyle, but I have no idea who they are so I am always wondering if someone is looking at me in a rather odd way if they’ve perhaps seen the pink bra under my white shirt or if they too are in on the secret. I had watched Katie and Reggie fuck furiously this morning, first getting him hard, then getting her wet, then licking and sucking both of them while they fucked like animals, then I had cleaned them up as they lay exhausted and was ordered out to do some shopping while they relaxed.
My cuckolding didn’t come as a result of my wife catching me watching porn or wearing her clothes, or to pay off some debt as you read about in so many stories, no my cuckolding came to be by a simple conversation between Katie and myself. Katie and I have been married for ten years. I’m fifty and she is forty. The advantages of getting married later in life are that you know what you want and the type of person you want. Katie was that person. Long hair down to her waist, wide hips, big breasts, thick thighs, tall and gorgeous. I am a BBW lover and went out of my way to find Katie and was pleased that she met that bill and much more.
A year ago a relative of mine died and left me a sizable inheritance allowing both of us to retire early, build our dream house in another state and sit back and enjoy life. One morning over breakfast Katie casually asked if I was serious about the whole cuckolding idea I had often told her about while we made love. I told I was and that it had been a long time life fantasy. She suggested that now we had the financial means we could make it happen, after all we were new to the area, no one would know us, we didn’t have jobs to worry about and all in all it might be a lot of fun!
After placing an ad online we sorted through dozens of dopey responses. Most people have no idea what cuckolding is really about or what is involved physically, emotionally and spiritually. The day before the ad was to expire we were about to give up when Katie said, “Hey, check this one out. Sounds like he could be a good candidate, and I certainly wouldn’t object to his physical characteristics!” That statement alone got me aroused and I went to the computer to check it out. Reggie’s response was concise, respectful, erotic, and honest all rolled into one. He was retired corporate executive at 60 and was shopping for a vacation home in our area and said he would love to meet us and get to know us and see where things went from there. He sent a picture of him on nude beach on the Riviera and he was quite the physical specimen. He stood about six foot three, muscular but now a steroid head, six pack abs, well toned, very good looking, and his cock hung like pendulum between his legs, and he was black!
Katie was immediately intrigued and emailed him back inviting him to dinner the following weekend. The week that followed had me lapping Katie’s ass and pussy as she talked on and on about Reggie and the size of his huge black cock versus my tiny white one.
I have to say she was right about that, my cock when I’m fully aroused and erect only measures four inches (yes Katie’s had me measure it!) and the fact that she likes keeping my body and head shaved makes me look even smaller. She would often comment on how my cock is only a half an inch when I am soft and how easily I cum as I licked her ass to orgasm. Katie would then allow me what she termed my ‘reward’ for licking her to orgasm. She would have me lie back on the bed and she would stroke my cock and tease my balls bringing me right to the edge of orgasm and then stop. She would sometimes do this for over an hour driving me wild and if I’d been a ‘really good boy’ she would acquiesce and right at the last minute let me shoot my load with her always aiming my cock so my load landed on my face.
The dinner with Reggie was splendid with Katie wearing a revealing low cut black dress that showed plenty of cleavage and came just about her knees showing off her gorgeous thighs. Her long red hair and pale white skin with the right amount of heavy make up made her look radiant as we walked into the restaurant and met Reggie at the bar for a drink. He towered over me and when he shook my hand it disappeared inside his and he almost crushed it with his firm handshake. We had drinks and small talk and then were seated in a booth with him and Katie on one side and me on the other. Needless to say I was already aroused by the whole evening but when the waitress came to take our orders, Katie ordered my food like I was a child and ordered the most expensive thing for her and Reggie and the least expensive thing for me.
After several martinies she was feeling no pain and began to openly flirt with Reggie telling him about our marriage and revealing at times the most intimate and sometimes embarrassing parts of our sex life and relationship. Reggie seemed to take it all in with great interest and I noticed a few times that his hand disappeared under the table and Katie would jump just a bit as if she was startled. Reggie excused himself to go to the bathroom and Katie looked me straight in the eye and said, “I want to fuck him! I want to fuck him tonight!” I was startled, excited, entranced, and aroused beyond belief. It wasn’t as if she was asking me, no it was her telling me she was going to fuck him! And fuck him she did! When we left the restaurant I drove as the two of them sat in the back seat and got more familiar with each other. I kept glancing in the rear view mirror and Katie kept telling me to keep my eyes on the road. I was instructed to drop them off at Reggie’s hotel and go home and wait for her.
That night was a turning point in our marriage. I waited at home like an expectant father, first cleaning the house, then trying to watch TV and finally logging onto the internet and surfing my favorite cuckolding sites. At 4 a.m. I finally succumbed and went to bed and dreamt of the imagined scenarios in my mind that my wife was currently involved in. The next morning I was up early making coffee when Katie walked into the kitchen looking absolutely gorgeous still wearing the same dress she had on the previous night except it was obvious she had no bra on and her hair and makeup were a mess. Immediately she walked over and kissed me long and deep reaching down and fondling my cock. “That was without a doubt the wildest night of sex I’ve ever had! He is the guy we were looking for and his cock is just as nice in person as it looked in the picture.”
The rest of the morning was spent with Katie regaling me with her nocturnal activities with Reggie. She described each act in great detail as I knelt between her legs licking her sore pussy gingerly bringing her to several orgasms. She made me put on one of my ‘outfits’ as she liked to call the clothes she bought for me while I licked and served her. Today I was wearing my pink tights and pink push up strapless bra, one of her favorites. After her fourth orgasm, she finally let me cum but teasing me to the point of having me beg and plead to let me cum. Finally she agreed but made me jerk myself off as she watched and made fun of my tiny cock size.
Katie took a long nap and woke in time for dinner which I had been slaving over most of the afternoon.
“You know honey I was thinking last night as Reggie and I were fucking. Since we get along so well and seem so compatible, I thought it would be a great idea for him to stay here while he’s searching for his vacation home. I mean there’s no need for him to pay for a hotel room while we have plenty of room here and plus it will be so much better for me to be able to fuck him whenever I want! Don’t you agree?”
There was really nothing I could say, but yes. I mean I had spent the past few years telling Katie how badly I wanted to be cuckolded and now she had found her man and was ready to move forward and I certainly couldn’t say no. “Reggie and I are going out tonight so while we’re out I want you to go to his hotel and get all of his clothes and luggage and bring it over here. For now put all of his stuff in your closet and you can put your stuff in storage. I already told Reggie about your outfits and he thinks that it would be a good sign of respect for him and subservience to me if you only wore your outfits around the house.”
That night while they were out partying and dancing I moved all Reggie’s stuff into my old closet and put my stuff in storage in the basement. Wearing a pink thong that belonged to Katie and a white camisole I made sure everything was hung and folded correctly. Reggie and Katie stumbled in the door at well after midnight both having been drinking heavily. Embarrassed, I greeted them in the living room and Reggie upon seeing me laughed out loud. “Damn girl you weren’t lying when you said you have him trained!” He eyed me up and down. “Katie says you’re cool with me moving in here?” My face was crimson with embarrassment as I nodded and said, “Yes Sir, welcome to our home, please feel as if it’s your home too and anything I can do for you please let me know.” He took Katie into his arms and gave her a kiss and I almost came in my thong. “Well for right now, bourbon on the rocks will do.” I hurried off and got him a bourbon and Katie a martini and brought them back on a tray. They clinked glasses; toasted each other and she took his hand and led him to the bedroom.
Sensual fucking is the only term I can think of to describe their sex that night. Her pale white body with bright red hair pinned beneath his coal black body, her legs spread accepting his huge swollen manhood with every thrust.
Every now and then he would pull out and take his massive tool and slap her pussy and clit with it which seemed to drive her absolutely wild. She looked at me and said, “You could never do this, your cock is way too small!” Reggie grinned at me and I almost shot my load. As he fucked her I was mesmerized kissing her feet and watching her toes curl (it’s one of her involuntary reactions to being aroused) so I knew she loved every minute of it.
That night they lay in each others arms, Katie’s head on Reggie’s chest, her hand on his cock, both of them semi dozing with me at the foot of the bed after having made myself cum with them watching and laughing, we all lay there sated and talking. Katie said how magnificent Reggie’s cock felt inside her and Reggie related how great it felt for him to get into that much younger white pussy and how tight she was. I told both of them how their interactions had made my fantasy come true and loved the fact that they both were having fun and wondered where we went from here. They both looked at each other and at me and snickered like the cat that ate the canary.
In the ensuing weeks and months Reggie and Katie began going out regularly and since we were all new to the area people just ‘assumed’ they were couple. They made friends and expanded their circle of acquaintances as I mostly stayed home playing house husband and making sure things were always the way they wanted them when they returned home. It was then that Katie told me one night that her and Reggie had shared our situation with some of their new friends going so far as to show them pictures of me in my various ‘outfits’ and telling them if they were to see me out in public they should come up to me and let me know they were friends of Reggie and Katie’s and were in on the secret. From that day forward every time I was sent out to run errands or for groceries I was always wondering in the back of my mind if people were looking at me because they knew or if I was just being paranoid. Of course I was always wearing an ‘outfit’ underneath my male clothes and since Katie had always kept me shaved from head to toe. I stood out from the crowd. Every now and then she would do something novel like put lip gloss on me that could’ve been worn by a man as a chap stick but had a gloss and sometimes sparkles. Another of her favorites was to apply the slightest bit of either eye liner or makeup always making me very self conscious about going out in public but excited at the same time.
My subservience became more apparent as we all adapted to our roles. I went from serving, to participating, to becoming proficient at oral sex on a male and female, licking, rimming, and cleaning up after their trysts. I looked forward to always learning more and more to please Reggie and Katie and if there was something one of them wanted to experience I would research it, and work hard at acquiring whatever skills were needed to master their needs and wants knowing that deep down inside serving them met my needs and wants. It’s always nice to know that I can please Katie or Reggie in some small way. Like when Katie thought it would be fun to take me with a strap on while Reggie watched a basketball game one night in our living room. The humiliation was exquisite as I knelt in front of Reggie as he sat naked with Katie behind me taking my anal cherry. His big, black, cock standing on edge as he stroked it sitting in what used to be my recliner in what used to be our living room!
The woman at the deli counter hands me the cold cuts I’ve ordered and as I walk up the health and beauty aisle a chubby brunette passes me and without stopping simply says, “Honey you should sashay that ass a little more when you walk.” My face turns crimson as I race for the register longing to get home from grocery shopping and see what Katie and Reggie have in store for me.