Cuckold Training for Bill Pt. 02

This is a retelling of the story "Cuckold Training for Bill" from Bill's point of view. You may want to read that story before reading this one.

*

I was sitting in front of my laptop watching porn. My wife, Lynn, was at her weekly coffee house get together with her friend Ann. I had my left hand inside my sweatpants fondling my cock and balls. On the screen I was watching a buff young man getting his large cock sucked by a shapely, gorgeous blond. She alternated between licking his shaft, licking his balls, and taking his cock into her mouth and bobbing her head up and down. Every so often she glanced to the side and gave a big smile. When the camera panned in that direction, it showed a dorky looking guy in a chair. He was naked and his wrists and ankles were tied to the chair. His smaller cock was erect. Since I had clicked on "cuckold" videos I knew he was the woman's husband. I had to wonder how the dork ended up married to the blond to begin with.

Lynn and I are in our sixties. Lynn is beautiful and sexy and I don't even mean "for her age." When her auburn hair began to gray she continued to dye it. Her face is gorgeous with big brown eyes. She is curvy in all the right places including nice breasts. Her sex drive has survived the aging process better than mine has, I'm afraid. As I aged my previously decent sized penis got smaller. I guess this is not uncommon although not universal. That wouldn't be so bad if it still maintained nice hard erections, but as soon as I was put on medication for my heart my erections suffered greatly. Yes I tried Viagra, but nothing helped.

Intellectually I know I should adapt and satisfy both of our needs by other means, but emotionally and psychologically I end up avoiding sexual encounters. I just feel like a failure when I don't get a nice hard erection. So I don't initiate or encourage it. Stupid on my part, but that's where I have gotten to. Of course I still enjoy sexual contact and cumming, so I end up watching porn and jerking off. Or sometimes just watching and fondling myself, enjoying the feeling of sexual frustration.

In the video, the stud had turned the blond around so she was bent forward and leaning on the bed facing the dork. The stud entered her from behind. Ten minutes of him pounding into her followed. As he fucked her she occasionally blurted out comments to her husband. "Oh, I'm so filled!" or "His cock is so much bigger than yours!" or "Go ahead and play with that little thing. After feeling this giant in me, your hand is all you are ever going to get!" or just general screams of pleasure.

As I watched her tits swaying as they fucked, I gripped my semi-hard cock, enjoying the feeling. Every few minutes I rubbed the precum around the tip massaging the head with my fingers. I enjoyed the feeling of frustration when I brought myself close to cumming and backing off as I watched. After the pair had orgasmed with many loud screams and exclamations, the stud pulled out and the blond walked over to the dork. As she untied him she said, "There is one job that you are qualified to do- the clean-up."

She sat on the bed next to the stud and dork walked towards her, dropping to his knees in front of her. She stopped him saying, "Don't be rude. Guests first." She pointed at the stud's crotch. The dork made a weak show of not wanting to before taking the big cock into his mouth and enthusiastically sucking off the accumulated mess. Then he stuck his face between the blond's thighs and licked the cream pie that was leaking from her pussy as well as the drips down her thighs. I was intrigued by the idea of feeling a cock in my mouth, but could not imagine doing it. Or, for that matter, tasting male cum.

I continued to play with my own cock while I watched a few more videos. Two guys 69ing. A femdom video where the Domme facesat on the sub and ground her pussy and ass into his mouth. Then I heard Lynn's car drive up and I closed down the laptop.

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One week later:

We were laying in bed and Lynn shocked me by saying, "Should we get divorced?" I was dumbfounded. A feeling of panic coursed through my veins. As I said I feel fortunate to be married to such a beautiful woman. I know we both enjoy our time together and doing things together. The thought of separating was awful. I could tell she saw the fear in my eyes.

"I hope not. I don't want to. I love you. Why? Do you want to dump me?"

"Not really. I love you too. But I need more sexually than you seem to want to give me."

"I can't help it! The meds—"

"I don't give a fuck about your erections or the small size of your dick! I just need more sex."

"I'll try and do more. I really will!"

"I've heard that too many times before and nothing has changed. I do have a plan though. Do you want to hear it?"

"Of course. Please."

"I want to be the sexual boss for a period of time. I'm not talking hours or days. I'm talking months. Or perhaps forever. Who knows."

"That actually sounds like it could be fun."

"There's more. You must commit to not cum until I allow you to. Not in the shower. Not watching porn. Only with me present and with my permission. It may mean some long stretches of frustration on your part, but I will promise you that it will be worth it in the end. You definitely will not regret it."

I was more excited than she knew. My submissive tendencies were dancing with joy in my head. The idea of being at her mercy and having sexual activities forced upon me was exciting as hell. My cock was even partially hard. Lynn reached out and placed my hand on one of her magnificent tits. I massaged it and kneaded it. Did the same on the other. Took her nipples between my fingers and made them hard and erect. She reached down and found my cock. She said, "Well, you seem to like the idea! Is it something you want to commit to? Remember, I'm talking for an extended time here."

I replied, "Yes, yes. I am all in!"

I continued to play with her tits while she toyed with my cock and balls. She captured some precum and used it to massage the head of my cock for a while. Then she gripped the shaft between a couple of fingers and her thumb. Starting slowly she pumped it up and down. Her speed gradually increased. I began to feel my orgasm approaching. My hips rocked matching her pumps. But just as I felt myself about to climax and shoot, she stopped pumping and pinched the base of my cock hard. I begged her to let me cum. She reminded me of our new agreement. I resigned myself to the frustration. My arousal receded.

Lynn said, "Very good. Now remember, you are not to jerk yourself off either. Believe me. I will know if you do. You're a lousy actor and a lousy liar. Those are not insults. That's a good thing. But I will be able to tell if you satisfy yourself. Part of the point is to push and frustrate you. Like I said before: I will make it worth it for you. That's a promise."

"I got it," I answered. She released my cock and rolled over to sleep. It took me a while due to the thoughts racing through my mind, but eventually I also slept.

She repeated the teasing of my cock- and the encouragement to massage her tits- on Thursday and Friday. Each time I begged to cum, but it felt more like a game than a real demand. I was actually enjoying the attention and frustration. All day long I was thinking about sex and Lynn's naked body.

She had even taken to coming up behind me at random times and hugging her tits against my back. Then she would reach into my sweatpants and grab my package while she ground her hips against my ass. Yes, I was liking this despite the frustration of not cumming.

On Saturday night she switched up her routine a bit. She started the same way but when I started getting worked up she got up on her knees and took my cock into her mouth. Her lips sealed around the base and she used her tongue to toy with my semi hard cock. My arousal level jumped. One hand stroked my balls. She sucked any pressure out of her mouth and my hardness increased. Her head bobbed up and down. I was sure she was heading for letting me cum. But when I was starting to explode she lifted her head and pinched off the base of my cock and frustrated me once again. On Sunday she repeated the activity.

On Monday she again started on my cock, but when she got up on her knees she moved up so that her pussy was above my face. She was facing my body. I looked up at her lovely pussy and admired her large labia lips. She continued fondling my cock as she lowered her pussy to my face. When it came close I lifted my head and swiped her pussy with my tongue. "Oh my, aren't you the eager boy." She lowered her pussy onto my mouth and I lcked and sucked loving her tastes and smells. She leaned forward. I felt her tits brushing against my abdomen and her mouth suck in my cock. She began to grind her pussy against my lips and tongue. She was real bossy, telling me to lick this and suck that. Aroused as I was, I wondered if I was going to be allowed to cum. But when I got close she again pinched me off as she shuddered in pleasure, reaching orgasm for herself. I licked her juices off my face.

On Tuesday she repeated this procedure but with one addition. After she pinched me off and reached orgasm herself, she straightened up, lifted up her hips, shifted a bit, and sat back on my face with her ass on my mouth. "Rim me," she ordered. My tongue went to work in and around her rosebud. I could feel her arm moving in such a way that I knew she was rubbing her clit. She built up, gave a big scream. And then relaxed in satisfaction.

"So are you enjoying being used as my toy?"

"For sure. And it's not like I'm not getting any benefits. I think about you and sex all day now."

"That's good. My plan is working then."

"How does this plan proceed?" I asked.

"Are you not enjoying being surprised so far?"

I admitted that I was finding the surprises very exciting. She mentioned that she wanted to get to sleep. That she was meeting Anna as usual in the morning. A worrisome thought occurred to me.

"Wait a second. Are you discussing all this with Ann?"

She replied that she and Ann discussed many things. She listed a bunch. I realized that she never actually answered my question.

****************************************************

The following Friday:

We were eating dinner and Lynn announced, "I want to go dancing!"

"You know I don't dance. I always feel foolish when I try."

"Well, I'm going. Alone or with you. Your choice. You don't have to dance, but understand that I am going to. You can sit and watch."

"Okay. I'll tag along and watch."

"I'll go get dressed." Lynn stood and added, "It doesn't take you as long to get ready so you can clean up here while I start."

A while later I joined Lynn in the bedroom. She was wearing this white, body hugging sheath dress that accentuated all her curves. The hemline was mid thigh. She looked sexy as hell. Not wanting to look entirely outclassed I changed from my usual sweatsuit into a shirt with collar and dress pants. Then we headed to a local club.

Most of the crowd was in their 20s and 30s but that didn't stop Lynn from being noticed. Guys were eyeing her up the whole time. We walked in. I sat on a banquette against the wall and slid behind a table expecting Lynn to sit in the chair facing me. However, she sat next to me. I realized that she wanted to be very visible from the dance floor.

Sure enough, she got a lot of attention. Guys walking by. Guys across the way. Even guys dancing with girlfriends were looking over their shoulders admiring Lynn. I realized that she was purposely giving upskirt looks and come hither glances.

It didn't take long before guys were asking for dances. And they sure got dances! Dirty dances! Lynn held them close and made sure they were feeling her tits against them. She ground against their bodies. They were grabbing her ass and holding her tight in return. She rarely made it back to me before being grabbed by her next partner.

Was I jealous? You bet. I could see how aroused these guys were when they pulled apart. I knew I was way past my prime. On the other hand, I was also aroused. My cock was stirring in my pants as I watched how sexy and desired Lynn was. I admit that I rested one hand over my package and lightly and unobtrusively fondled myself.

Lynn must have noticed because she stopped by to remind me that I was not permitted to cum. Eventually Lynn had danced enough and we headed home. I'd had a few beers so she drove. She rested her right hand on my crotch and fondled and pinched my cock through my pants. I asked, "So do I get to cum yet?"

She replied in the negative and reminded me that when I did it would be worth it.

When we went to bed Lynn told me, "You are going to find out just how turned on I got from grinding against those young guys and their stiff dicks. And their hands all over my ass. Lay down on your back. Next thing I knew she was slipping her panties over my face, the moist gusset right over my mouth and nose. I inhaled her sexy aroma and felt how soaked they were as she worked my cock with her hands and mouth. I found the feeling of my cock in her warm, wet mouth luxurious. And the way she ran her tongue along the most sensitive areas was amazing. When she had me really going she rapidly jerked me. I started feeling the cum ready to explode. Of course, at that point she stopped and watched my cock spasm in the air without any relief for me.

"AAArgh. Please?" I begged. She just smiled as my cock shrunk down and softened.

On Saturday Lynn told me that she'd had so much fun the night before that we were going out again. She wore another tight sexy dress- red this time. As we were heading out the door she lifted the hem and flashed me- to make sure I knew she wore no panties this time. She already had me excited.

At the club she again danced close and tight with a bunch of guys, letting them feel her up and rub the front of their pants against her body. This was in addition to sharing upskirt looks at her bare pussy any time she was seated. Again I felt a strange mix of jealousy and arousal.

When we got home and went to bed, she ordered me to worship her pussy, to bring her to orgasm, and to clean the area up. Then she went to work on my cock in what was now the usual way. Alternating between hands and mouth. When her mouth was free she shared some thoughts.

"That blond haired guy drove me nuts. His cock was rubbing into my stomach the whole dance. It was so big and hard!"

"That red dress is such soft material that when I rubbed up against those guys I could feel their hard cocks rolling between us."

"I think you would love it if I invited one of those guys home with us. If you could watch him bang his big cock into my pussy and make me scream with pleasure."

"Just hearing about all this is making your prick hard! I think you love the idea of being cuckolded by a young guy with a bigger and harder cock than yours."

And she was right. I didn't admit it but I was very excited by the idea. Of course at that point she let go of my cock and got off the bed. "Calm down, my little guy." And I had to let my excitement subside once again.

The next interesting event was Tuesday evening.

Nothing seemed out of the ordinary. Then the doorbell rang. I answered it and there was Lynn's friend, Ann. As gorgeous and sexy as always. I invited her in and she joined us in the living room. She sat on the sofa next to Lynn across from my recliner. They may both be past sixty, but they were one beautiful sight- both pretty, curvy, and wearing sexy skirts showing nice legs. And Ann wasn't exactly being ladylike, if you get my drift. She was relaxing her legs and separating her knees giving my horny eyes amazing views of her curvy, strong thighs and her panties. I didn't worry about her noticing that I was looking. She seemed to be encouraging that.

Then she surprised me. She threw one arm around Lynn's shoulders and ran the other under her skirt- massaging her thigh and teasing it near Lynn's panties. They began to make out. Ann continued to rub Lynn's thigh area. Lynn was rubbing and fondling Ann's tits. I was sitting, watching, and pressing my hand against my cock, feeling it getting harder.

Then Lynn looked at me and told me to get naked. She added that I could touch myself but that I better not cum. Keeping my eyes on the exciting scene in front of me, I stripped off my clothes and sat back down, hand gripping my cock. They continued making out and feeling each other up for several minutes before Lynn interrupted and said, "Let's take this to the bedroom."

Was I going to be allowed to cum? To play with two hot women? I did not dare let my expectations get too high.

Sure enough, when we got to the bedroom I, being already nude, started to get on the bed.

"Ahem," Lynn said. "Sit in that chair in the corner. And no more touching yourself."

Damn. I was very disappointed. But I was soon too busy observing for the disappointment to last. The two ladies both stripped from their clothes and climbed onto the bed. They embraced and spent the next ten minutes rubbing against each other and each running her hands over the other's body. Then they spent a few minutes taking turns sucking on the other's nipples. Then Ann pushed Lynn onto her back, swung around into 69 position and began licking Lynn's pussy. Of course, Lynn was returning the favor. Satisfied moans floated through the air. I squirmed in my arousal wanting to fondle myself, but I didn't dare push it.

Then Ann got up off Lynn and laid down leaving room on the bed between them. Lynn looked at me, smiled, and patted the empty space between them. "Join us." Like a shot I was lying on my back between them, surrounded on both sides by gorgeous tits- round and soft with swollen nipples. My hands stroked and cupped the breasts. My mouth sucked in the nipples. My tongue played with them. I felt hands and fingers playing with my aroused cock and balls. The women moved down on the bed, adding their mouths and tongues to stimulate my cock.

A few moments later, Ann was pumping my shaft. Lynn had the head in her mouth.

"Oh My God," I said. "Are you going to let me cum?"

Lynn stopped sucking and answered, "Hmm. I'm considering it."

"Oh, thank you, thank you, thank you."

"Don't thank me yet. There will be one more condition."

"I'll do anything. Just make me cum."

Her answer surprised me. "You have to promise to eat your cum."

I only hesitated a few seconds. I could feel the load building in my balls. I couldn't stand the thought of being pinched off again. "Okay, I promise!"

Ann increased the pressure between her fingers and the speed of her jerking. I felt myself bursting and my cum exploded. Ann had my cock pointed towards Lynn's open palm. She caught my load as I ejected several shots. The reality of my promise now sunk in. There had been many times in the past that I had considered tasting my own cum. There had been times I had jerked off fully intending to do so. But once I shot my load into my hand I always lost the urge to actually take it into my mouth. The most I had ever brought myself to do was to touch it with my tongue to get an idea of the taste.

But here was Lynn's hand approaching my face, the palm full of my load. Instinctively I pulled back. The women expressed their disappointment in me that I would break my promise. So I opened my mouth. Lynn pushed her palm against my open mouth and rubbed it downward using my lower lip to scrape the cum in. I licked her palm clean and swished it around in my mouth. After an initial bad impression I decided that it tasted, let's say, interesting. Salty. Sweet and sour at the same time. Hard to describe. I swallowed it down.