I wrote a pervious story, “A Friend in Need: Part 1 – Sucking Tom”, and this is a follow-up to that story. That story involves me being cuckolded by my best friend, whose cock I have been sucking regularly since the encounter in the first story.
My friend, Tom, was sharing a hotel room with me when a series of events lead me to sucking him and admitting my cuckold desires. I told him that I would help him if he wanted to try to fuck my wife Joan. Several months following when I discovered my true bisexual nature on that business trip, Tom was still feeding me his cum about once a week, and he was constantly pestering me to help him fuck Joan. I agreed to help him but was certain that my conservative wife would never fuck another man.
I was thirty-six years old at the time of this story, and my wife Joan was thirty-four. Joan is five feet and six inches tall and weighed about one hundred and twenty-five pounds then. She’s a beautiful brunette with sparkling green eyes, and has a slim waist and gorgeous 36D breasts, which were still rather firm, given that she breast fed our two kids. We had a fairly good sex life, but because my cock is small and I cum very quickly, it had become routine for me to orally bring Joan to orgasm after I shot my load. I didn’t seem to mind the taste of my own cum since I also have my mouth on Joan’s beautiful and tasty pussy.
My problem in setting up an encounter with Tom was that Joan was a virgin when we married and had never been with another man or experienced another man’s cock. I’m not sure that she had even seen another man’s cock in pictures. She had never expressed an interest in another man, and was happy with the orgasms that I provided orally, even though I know that my small cock couldn’t really satisfy her. So, I had to find a way to get her interested in being with another man, without her totally losing respect for me.
It was on a business trip that I came up with an idea to at least introduce Joan to the concept that I was excited by reading cuckold stories. I picked up a copy of ‘Penthouse Letters’ at the hotel and brought it home with me. The stories were very good, and I enjoyed reading all of them on my trip.
I also liked to read many other creampie and cuckold stories on the various Yahoo sites, but I didn’t dare let her know about that yet. I left the magazine half hidden under my folded shirts on the closet shelf, hoping that Joan would discover it. Several days later when we were getting into bed, Joan confronted me with the magazine she found in the closet.
She said, “Ed, I found this trashy magazine on the shelf, and want to know what you are doing with it. I read some of the stories that you had dog-eared, and I can’t believe that you read that stuff!”
I said, “Sorry, honey, I didn’t mean for you to see that. I found the magazine in my hotel room drawer on my last business trip, and couldn’t help but read some of the stories. I had no idea that there were stories like that, or that people would really do those things.”
Joan was getting pissed and said, “Tell me, do you enjoy reading this filth? Do you think about you and me in those situations? When did you start thinking about this? Aren’t you happy with our sex life?”
I hadn’t really expected Joan to be that upset, so I tried to diffuse the situation. I said, “Look, Joan, I found the magazine and read a few of the stories, and it’s not like I went out looking for it. Some of the stories caught my attention because they were about husbands with smaller-than-average dicks, and you know that I can’t always satisfy you with my dick. So, it was just a passing interest to me, and I can throw it away if you want me to.”
Joan was starting to calm down a little, but said sarcastically, “No, Ed, if you want to read that stuff then just keep the magazine, but keep it out of my sight!”
Obviously, Joan was not aware of all of the other porn that I was reading online, and I can only guess how mad she’d be about that. At least I had introduced the idea of cuckolding to Joan, and I found another hiding place for the magazine in a drawer in our closet, being careful to keep it hidden and noting exactly how I had placed it there. Joan seemed to get over being angry with me, and she didn’t bring it up to me again, which as I look back is a little unusual for a wife who was as angry as she was.
About three weeks later, on a Saturday morning, I went to get the magazine and read a few stories to masturbate to, since Joan was out shopping with the kids. When I looked in the drawer, I noticed that the magazine had been moved just a little and also noticed that some of the pages had been crinkled. The only conclusion that I could reach was that Joan had been secretly reading the stories, and the way I had the magazine hidden, it could only mean that she had searched for it. I was elated with that turn of events and planned my next move for that evening when we went to bed.
When we got into bed I said, “Honey, remember that magazine that you were angry about and wanted me to hide? Well, I went to find it today and noticed that it had been moved. Have you been reading it?”
Joan’s faced turned red with embarrassment and she hid her face in her pillow and began to weep. I rolled over next to her to hold her and told her that it was alright. She then said, “I’m so sorry, Ed, it’s just that when I first found the magazine I couldn’t believe the size of some of those penises, since yours is the only one I have ever seen before. I then felt that since you seemed to enjoy the stories, I should at least try to understand what you liked about them. I’m so embarrassed that you found out, but I have to admit that I did enjoy some of the stories.”
I asked her, “Well tell me, which stories do you like the best?”
Joan then hesitantly said, “I kind of like the ones where the husband has a small penis, and he fantasizes about his wife being with another, well-endowed man. I’m happy with our sex life, but I have to admit that those stories really get me wet!”
I said, “Please, honey, don’t be embarrassed or upset. It makes me happy that you find the stories exciting. Maybe reading them will spice up our sex life a little.”
Over the next several weeks we continued to talk about the cuckold stories, and Joan was getting more comfortable with us discussing our desires openly, and she even started using more-graphic language. We soon started talking about adding role play fantasies to our sex life, and she began to pretend that I was a big-cocked friend fucking her, and then getting off on me sucking the friend’s cum from her pussy.
At first that was an anonymous, unnamed friend, but then we began to discuss different men who turned her on. Since Tom and his wife Denise are our best friends, and since Tom is a handsome and well-built guy, we started talking about the possibility of making him Joan’s fantasy fuck.
One night Joan said, “You know, one time when we were having a party and Denise was drunk, she confided in me that Tom has a big, eight inch cock and that it’s also very thick. She also said that Tom seems to have an insatiable desire for sex, and she sometimes found it hard to keep him satisfied.”
Little did Joan or Denise know about Tom’s activities on out of town business trips, where he tried to fuck anything in a skirt, and usually succeeded. I was beside myself with joy! There was Joan bringing up Tom and his big cock as a fantasy, and I knew that I had to push it a little more.
I said, “Honey, if you want to we can fantasize about Tom being your stud.”
Joan then said, “But, Ed, how would you handle thinking of your best friend fucking me and then you eating his cum?”
I said, “Look, Tom is my best friend, but I have to admit that it does turn me on a little watching him naked in the gym showers with his big cock and balls swinging, and I couldn’t think of anyone better for you to fantasize about fucking you. And besides, this is just our fantasy.”
Denise seemed a little surprised that I would be watching Tom in the showers, but she was happy to think of him as her stud.
The next time I saw Tom was at the gym on Monday morning, and I couldn’t wait to tell him the progress that had been made towards him fucking Joan and cuckolding me. He was pleased that he was the new object of our fantasies, and I noticed that later, when our families were together socially, he was beginning to pay a lot more attention to Joan. But he was careful not to get caught flirting too openly with her.
Tom asked me if Joan knew about me sucking him, and I said, “No, Tom, I just couldn’t tell her that. It’s bad enough that she knows that I’m fantasizing about sucking your cum from her well-fucked pussy, but I could never tell her that I regularly enjoy sucking your big cock and balls.”
Tom’s flirting fueled Joan’s fantasies even more and she started verbalizing Tom’s name when we fucked. Joan would say, “Fuck me, Tom, fuck me with that big cock and fill me with your potent cum!”
And then after my small cock left her unsatisfied, Joan would pull my face into her pussy and say, “Go ahead, Ed, eat my pussy and enjoy the cream from Tom’s big cock!”
Our fantasy sex involving Tom continued for several more weeks, and Joan became more and more vocal about enjoying the fantasy fucking that he gave her and her joy at having me eat his cum. Even with all of the fantasizing, about Joan fucking Tom and me eating his cum, I don’t think that it had occurred to Joan to really make it happen. Then, a set of circumstances occurred that allowed me the chance to take it to the next level of having Joan cuckold me.
It was summer time and Denise had taken their kids to another state to visit her parents. That meant Tom was home alone, and since he was our best friend, it was only right that we have him over to dinner with us. Our kids were away at summer camp, so we had the house to ourselves.
I told Tom that would be the chance that he had asked me for, and that I had done all I could do to get Joan in a frame of mind to cuckold me. He was very confident that he could fuck Joan, and even though I was aware of the success that he usually had with women on business trips, I still didn’t think that Joan would let Tom Fuck her.
The big day came, and since Joan was not aware of Tom’s plans to cuckold me, she didn’t seem to dress in a necessarily seductive way. Joan wore a simple, thin sundress, but I did notice that she wore a pair of thong panties, but no bra since her breasts are firm and didn’t need support all the time. Tom came over and we had a barbeque out by the pool.
I noticed that without Denise and the kids around, and with Tom knowing that I supported his efforts to cuckold me, he was more openly flirting with Joan, and sat next to her and engage her in conversation, and touch her arm to make a point every now and then. I was beginning to feel like an outsider in my own home, but I was so excited seeing the attempted seduction unfold that I had a raging hard on.
I was starting to see a little change in Joan, and she was paying more attention to Tom than she normally did, and I thought that I saw her checking out the bulge in his shorts a couple of times. I couldn’t help but assume that she was thinking of our fantasies, and wondering what that bulge in his shorts would feel like in her wet pussy. However, other than Tom and Joan being more engaged in conversation than usual, the dinner was uneventful, and I was beginning to think that I was right about Joan not cuckolding me.
Following dinner, I started cleaning up the patio and pool area and Tom helped Joan carry the dirty dishes into the kitchen and clean up the pots and pans. It was getting a little late in the evening and from my location on the darkening patio, I saw Joan and Tom in the kitchen at the sink, and I was close enough to hear their conversation. Joan placed both hands in the water and started scrubbing a pan, and Tom moved up behind her as if to help.
I heard him say, “May I help you with those pans, sweet lady?”
With that he moved up behind Joan and reached around her, putting his hands in the water with hers. He was standing very close to her, and even touching her, and I was anxious to see Joan’s reaction.
Joan said, “Tom, you really shouldn’t be standing so close to me. What would Ed think if he saw us?”
I’ll never forget Tom’s answer when he said, “Somehow I don’t think that either you or Ed will mind if I press myself against you, and I know that you have fantasized about this many times.”
I couldn’t believe that Tom told Joan that he knew about our fantasies, and I knew that I’d be in big trouble with Joan for telling him about it.
Joan said, “What did you say? Are you telling me that Ed told you about our fantasies? What else did he tell you?”
By then Tom was pressing himself against Joan’s back, and I know that she couldn’t help but feel his large cock up against her ass and lower back, and she was starting to look a little flustered. Tom then brought his wet hands up to Joan’s breasts, and held them, with only the thin fabric of the sundress between them. Joan struggled briefly, but I saw through the wet fabric that her nipples were hard and she was getting turned on by Tom’s holding her breasts and pressing his enormous cock against her.
Tom continued, “That’s not all, Joan. What if I told you that Ed has been sucking my cock almost weekly for the past six months, and that one of his favorite fantasies is for me to fuck you with my big dick and then suck my cum from your pussy?”
I couldn’t believe that Tom had betrayed my trust by telling Joan that I had been sucking him, and it looked to me like he was trying to get Joan angry with me so he would have a better chance to fuck her. Tom’s coarse language and physical touch, coupled with her anger at my betrayal, were having their effects on Joan and she said, “Well, Tom, if my cock sucker husband wants to see me fucked by your big cock then let’s give him what he wants!”
Joan then turned to Tom and kissed him deeply, just like she had fantasized about so many times before. Tom also loosened and dropped his shorts and underwear, leaving his massive cock bare between him and my wife. Joan continued kissing Tom and also began to rub his cock, and I saw the joy on her face at finally getting to fondle the source of so many of our fantasies .
Then Joan said, “Tom, let’s take this to the bedroom, and I’m sure that Ed is watching us and will follow.”
I was feeling embarrassed and sheepish about Joan knowing my role in her seduction and that I was also sucking Tom’s big dick on a regular basis. However, I was drawn to follow them to the bedroom, and I couldn’t believe that my favorite fantasies were about to come true. Joan and Tom walked hand in hand to the bedroom with me following them, and when we got there Joan removed her sundress and thong, leaving herself totally nude in front of him.
Tom also removed the rest of his clothes, and it was an awesome sight seeing them naked together like that. Joan fell to her knees in front of Tom and took his swollen member in her mouth. Tom’s cock is so much larger than mine, and Joan looked at it almost as if to worship it. Tom’s balls were also hanging heavily, and Joan massaged them as she began to suck his dick. After a few minutes of Joan sucking Tom with him rubbing her gorgeous breasts, Joan got up and pulled Tom to our bed.
Then Joan said, “Come here, Ed and lay down on the bed, I want you to see Tom fucking me up close, just like in our fantasies!”
With that I lay down on the bed and Joan got on her knees over me in the sixty-nine position. Tom got on the bed and approached Joan from behind, and the sight of that massive cock and low-hanging, heavy balls was incredible.
Tom then said, “Go ahead, Ed, suck my cock to get me ready for Joan’s sweet pussy.”
With that, Tom forced his cock in my mouth, and I saw Joan looking down at me with a smirk on her face, watching me eagerly suck Tom’s dick.
She said, “Gee, you were right, Tom, look at that hungry cock sucker go. I think he loves your meat more than I do.”
Tom then pulled his cock out of my mouth and started to insert it in Joan’s beautiful wet pussy. What a view, seeing her vulva spread to accommodate Tom’s girth! He slowly entered her, and I saw Joan’s inner labia being pushed in deep as Tom was on the down stroke, and being pulled out as he pulled out of her. I pushed my face up to suck Joan’s clit as she was being fucked by that awesome cock, and I could feel Tom’s dick and huge balls sliding over my face.
From time to time Tom would slow or stop his thrusting and I would rise to suck his balls, as he slowly rotated his hips and ground his meat into my wife’s pussy. I saw his ass flexing as he held his cock deeply in Joan’s tight pussy, and I knew that he was touching places in her that I have never reached with my small dick.
The fucking continued for a long time, and I know that Joan was enjoying the first real fucking that she ever had. She was constantly moaning and asking for Tom to thrust harder and deeper. I then saw Tom’s balls start to draw up and I knew that he was nearly ready to pump his cum into Joan’s pussy.
I heard him give a grunt, and then he held himself tightly in Joan’s pussy, and I saw the base of his cock throbbing and pulsing as he unloaded his semen and sperm into my wife. After Tom finished ejaculating, he began to slowly thrust in an out of her, both to enjoy the wetness and tightness of her pussy, and also to make it clear that he was the stud, and he wanted Joan to know the power in his big cock.
Tom continued to slowly stroke Joan’s pussy, and from my position under her I saw their combined juices start to ooze out of her around his deflating cock. I began to lick her pussy and his cock, and tasted the familiar juice from my wife and Tom’s cum. That was the happening that I had dreamed of for so long. After a few more minutes of that slow thrusting Tom pulled his cock completely out of her pussy.
Then Tom said, “Okay, Ed, make your fantasies a reality, suck my cock covered in Joan’s sweet juices and my seed!”
I took Tom’s cock deeply in my mouth, and since it was partially deflated, I could take all of it.
Then Joan said, “Tom, please move away so I can give Ed the real meal that he desires.”
So, Tom moved out of the way and Joan sat up, with her pussy pressing heavily on my open mouth. She then flexed her stomach muscles and said, “Here it comes, Ed; don’t miss a drop of our juices.”
And with that, a steady flow of their combined fuck slop flooded my mouth, and it was all I could do to swallow it without choking. I continued to suck Joan’s pussy for several more minutes, and she vigorously fucked my face to another huge orgasm, which caused even more of their fluids to fill my mouth.
That was the end of a wonderful first experience, but now that Tom had become her stud, and I was her cuckold, there were many more similar experiences that we shared together.
