Evolving as a cuckold - through the seasons of life

[venus-can99]

Caroline cuckolded me fairly intensely the summer after Blake, with a young "farmer" named Tab in Northern California while worked but ass off getting things wrapped up so we could leave the Rockies and head to the Twin Cities - the next step n the adventure of life.

Wanna hear the tale?

Yes to both - Caroline's post Blake adventures and the next chapter in the twin cities

[shadowtantra]

looking forward to hearing more when time permits!

[The Owl]

Caroline spent about two months visiting her sister - Nancy - in Northerm California while I was finishing the last details of my training program in the Rockies.

There were no cell phones in those days, no email... just expensive long-distance calls, billed by the minute, and letters which created a lag of several days between each volley in the question-answer cycle.

Nancy lived in a house in California with her boyfriend. They had a 3 year old son together and were expecting another baby in a few months. Nancy was a free-spirit who pushed the envelope every chance she got from high school forward. She was a flower child of the 60s. Her boyfriend’s “front” was that he owned a construction company. In fact, he was making most of his living growing plants. Nancy and he told his son that they were "tomatoes plants” to avoid the child blurting out the truth to somebody. His "farming" partner was a guy named Chance. Chance's live-in girlfriend was in Boston for the summer studying ballet. I didn't know anything about Chance until Caroline returned to the Rockies at the end of the summer. Chance’s house was walking distance from Nancy’s.

When I called Nancy's landline about once a week, Caroline and I enjoyed short conversations. She sounded like she was enjoying herself in CA. As the summer progressed, there were a couple of calls that felt slightly odd. Once, Caroline sounded very distracted. She told me that Nancy had company and that it wasn't a good time to talk so the call needed to be brief. Another time, Nancy answered and told me that Caroline wasn't there. I naively asked where she was and when she might be home so I could call back and talk with her. Nancy was dodgy with her answers and kept everything vague. I didn't think too much about it. Within a few hours, Caroline called me back and we chatted.

At summer's end, I picked Caroline up at the airport and drove her to our cabin on the edge of town. Caroline unpacked. I was longing to be naked with her after a couple of months apart. There was a chill in the air so I started a fire in the cast iron stove. We lay down on a flannel sheet over a futon on the floor close to the stove. The glow from the stove warmed both of us.

Clothes began slipping off. Soon, my naked body was above Caroline's. I began nudging the head of my erect cock between her legs, into her wetness.

Everything felt familiar, until we started moving our hips in synchrony. Her pelvis moved differently than I remembered. It wasn't a huge difference, but she had a slightly different motion and rhythm her her hips as her body responded to mine. Her pussy felt the same but it was as if her pelvis was looser and could move more easily and vigorously than had been the case before she left for California.

We were both eager for release. After we had both enjoyed our respective orgasms and were relaxing, with the radiant heat from the wood stove adding to our post-orgasm afterglow, I inquired whether Caroline had been with anybody while she was gone for the summer.

"What do you mean?"

"While we were making love, I could feel your hips moving differently than I remember. It felt as if you had been taking dance lessons while you were gone. There’s something slightly different about you."

"Really?"

"Yes. Tell me about your time in California."

"Do you want me to tell you everything?”

“Yes.”

Caroline curled her body into mine and began telling her story as she ran her hand affectionately over my torso.

“After I settled in at Nancy's house, she had a dinner party to introduce me to their friend, Chance. His girlfriend moved to Boston for the summer to study ballet. I told Chance about you. He told me about his girlfriend whom he loves. He clearly was missing her company. We enjoyed getting to know each other over dinner.”

“And…”

“A couple of days later, Chance invited me over to his house and cooked dinner for me. He’s a very good cook. One thing led to another and he invited me to spend the night.”

“Did you sleep with him?”

“Yes. It's a small house and they only have one bed.”

“Go on… I’m listening.”

You remember when you called and I wasn’t at Nancy’s house?”

“Yes. And then you called me back.”

“Well… I called you back from Chance’s house. I was careful never to answer the phone at his house because it could have been his girlfriend calling and I didn’t want to cause her or Chance any distress.”

“It sounds like you spent a lot of time at Chance’s.”

“Well… Nancy’s house is also quite small. They have their 3 year-old running around. It quickly became apparent to all of us that it would make more sense for me to stay over at Chance’s house rather than sleeping on Nancy’s couch. So I did.”

“So… you were living together?”

“Chance had to get up early each day for work and he didn’t come home until early evening. I could walk back and forth to Nancy’s whenever I wanted. I enjoyed the peace and quiet at his place during the day. Chance was very comfortable sharing his home with me for the summer. But he did not want his girlfriend to find out. She would have been very upset. He told me she tends to be possessive and jealous.”

“So, you two were making love all summer?”

“We enjoyed each other sexually, but we weren’t 'making love'. He loves his girlfriend. We were both solo for the summer. We both could feel the sexual chemistry between us from that first dinner. Don’t make it into something bigger than it was. It wasn’t making love.”

We quietly paused our conversation in the heat of the fire. I was naked and erect. Caroline touched my cock and said seductively, “My hand tells me that you found my summer fling story arousing. It’s interesting to me that you detected something different about me when we made love. You know me very well… my every movement.”

Soon… I was in her again… Slowly climbing toward the peak of our mutual pleasure.

While approaching my second orgasm, I whispered through Caroline’s hair, close to her ear, “Was he good? Did you enjoy his cock?”

“Yes…” she moaned… “Yes... Oh fuck… Yes…”

[Rogueuser1]

Nice! That is a hot update. I wonder how many times he had sex with her during that summer fling. What a great two months!

[venus-can99]

Thanks for the HOT update Owl. Sounds like Caroline had a great summer with Chance. Did you have any female company in the Rockies in her absence or did you remain chaste?

[The Owl]

Nice! That is a hot update. I wonder how many times he had sex with her during that summer fling. What a great two months!

She never gave me a count but she slept with him almost every night for two months.

Thanks for the HOT update Owl. Sounds like Caroline had a great summer with Chance. Did you have any female company in the Rockies in her absence or did you remain chaste?

Good question. I was not chaste. I will tell that story another time. But from a quantity perspective, Caroline had me beaten at least 50 to 1.
When I disclosed my brief encounter of the skin kind to Caroline, she was happy to listen. My experience let her off the hook regarding any guilt she thought she was suppose to fee for having lived with Chance for the summer. But guilt was never a big theme for Caroline.

[The Owl]

So... I know I have gotten this story out of sequence from time to time.

Several months before Caroline's summer with Chance in CA, she had been with Blake in the house in which I had lived while we separated for a few months. I knew about Chance immediately upon her return. I didn't know about Blake until several years later, when she disclosed the ancient tale.

After the summer with Chance, we left for the Twin Cities for a year, then to the island town on the west coast of North America, and then to a a mid-sized city in the NW. Lots of changes and experiences along the way.

More to come. It's a long, delicate, and wandering story... just like life itself.

[venus-can99]

More to come. It's a long, delicate, and wandering story... just like life itself.

Thats what makes this so adorable. As they say many times truth can be stranger than fiction.

[thepen]

I just wanted to add my appreciation here, Owl, for this thread which I've only just stumbled on. Your style of writing is endearing, and I wonder if you've ever thought to turn all this into a novel. Like a "based in truth" but embellished if necessary story. You have a way with telling. Anyway, thanks for sharing it all.

[The Owl]

I just wanted to add my appreciation here, Owl, for this thread which I've only just stumbled on. Your style of writing is endearing, and I wonder if you've ever thought to turn all this into a novel. Like a "based in truth" but embellished if necessary story. You have a way with telling. Anyway, thanks for sharing it all.

Thanks for the feedback. I'm glad you enjoyed. Reading novels is becoming a bit of a lost skill in today's world of screens. Staying focused for more than a few moments on one source of stimulation is the exception, not the rule. When I watch people furtively scrolling on their phones, look away, and then scroll some more, I realize that the days of spending 10 hours reading one book have slipped into the rear view mirror. Then again, maybe I'm wrong.

Anyway, thanks for your feedback.

[The Owl]

Twin cities...

After the summer of "Chance", we moved to the Twin Cities for a year. I've already written about one experience there - afterhours at the hottub shop.

Bear in mind, this was the PPPP era (i.e., post-pill & pre-plague). Sexual experimentation was in full bloom throughout America.

Caroline worked with "W" at a small personnel recruitment office ("head hunters"). Caroline had met W's husband, "H", when he visited W at work one day. W & H were about the same age as us. She was fit, perky, pretty, and engaging. W came by our apartment one day on her way home from work. She wanted to meet me. After some small talk, she invited us to have dinner at their home the following weekend. When she was getting ready to leave our apartment, she moved closer and hugged me goodbye. I welcomed her hug with open arms, so to speak. Before releasing the hug, she lightly kissed me on the lips. I enjoyed her move but it was fleeting with nothing more than momentary contact of our lips - a bit more than a friendly hug, but not an intensely erotic French kiss. Caroline was standing next to us and did not seem to mind W's quick kiss on my lips. W moved over and hugged Caroline. Then, she was off.

When we went to W&H's house for dinner, he proved to be handsome and engaging - a good conversationalist. Dinner was enjoyable. We shared some wine. They were antique collectors and had two upholstered chaise lounges in their living room. Their sound system was there too. They invited us to move from the dining room table to the chaise lounges. W lit some candles and turned off the lights, while H put some jazz on the turntable. They both encouraged us to lay back on our chaise lounge to enjoy the ambience. They did the same on the other chaise lounge. We chatted about this and that, and continued getting to know each other. The upholstered chaise lounge chairs were narrow enough that we were each entwined with our respective partners. Otherwise, there wasn't room to recline together. In the darkness, in synch with the improvisational jazz, I could hear W being affectionate with H while he talked. It sounded like she was kissing him on the neck. There were a few giggles and a few moments of silence while the jazz continued to spin. The energy in the room felt erotic but also lighthearted. There were so many ways the evening could have unfolded from there.

Looking back, it was clear to me that if I had suggested that Caroline and W switch places, both women probably would have agreed. If that had occurred, W would have begun kissing me, and Caroline would have improvised her own style of jazz with H. Assuming nobody became overwhelmed with anxiety about what it all meant, and assuming that we all followed our respective instincts, the evening could have easily evolved into full swap with all four of us in one room.

There was eroticism in the air. But nobody - including me - had the guts to make the first move. They kissed a bit on their lounge as did we, but nobody took it to the next level. We could have gotten naked with our own partners and had parallel sex, with no swap involved. So many options but none were acted upon. Eventually, Caroline and I decided it was time to bid them adieu and we headed home. Although we all enjoyed the evening, the four of us never got together again. The reason for not getting together again may have had something to do with office politics - I can't remember. I just know there was not a second chance. That erotic moment came and went.

A missed opportunity... full of erotic promise.

[venus-can99]

A missed opportunity indeed... I guess no edibles or other ways to drop inihibitions were available at that time..

[The Owl]

And now my memories of the Twin Cities are flooding into consciousness...

Saturday night party... mostly people from my workplace. Drinks flowing... Music blaring through the host's house. We are all dancing in the living room. I'm not sure who Caroline was dancing with but I'm guessing she was having fun. It was the type of party where the dancing did not require a partner although many people were paired up. I found myself dancing with a very attractive flight attendant who had flown home to the Twin Cities earlier that day. She was single, young, and frisky. I enjoyed dancing with her.

A female coworker of mine was close by with her boyfriend whom I had not met before. He was working up a sweat with his dance moves. We were all having a blast. All at once, her boyfriend stopped dancing, looked at the ceiling, and yelled, "Dominate me!" The flight attendant laughed, his girlfriend smiled, and the dancing continued. It wasjust a momentary slice of life but it was an interesting one. I wonder how my coworker and her boyfriend worked things out behind closed doors. I'm guessing he liked her to "dominate me." And, I'm guessing she did too.

[The Owl]

Another Twin Cities memory from 40+ years ago.

I had read Penthouse Letters about "wife watching" during that time but these events occurred long before the words "cuckold" "hotwife" and "bull" were common parlance. Looking back, I encountered all three characters in one home over dinner.

To provide context, I'm now certain one of my male coworkers in the Twin Cities was bisexual. He was married but occasionally hinted somewhat obtusely that he thought it would be fun to experiment sexually - to push boundaries. He kept it all very abstract and wasn't directly hitting on me. I was too naive to know that a married guy might be bisexual and I really wasn't interested in responding to any of his innuendoes, so I just let such comments slip on by. He was a nice guy and I enjoyed working with him. Let's call him "Z". He was bright but he was not very handsome.

Z had not met Caroline and I had not met Z's wife - let's call her "A." Z invited Caroline and me to come to their house for dinner one Saturday evening. We accepted. They lived in a small house in the suburbs. When we arrived, we were greeted at the door by A. I was surprised by her beauty. She was also personable and immediately engaging with both of us. We felt welcomed by her.

Given the fact that Z was not much to look at, I was a bit surprised that his wife was so beautiful. He had married "the girl next door" who was much more visually attractive than him. She had fair skin, a great body, long brown hair, and bedroom eyes. She didn't have to wear a lot of makeup or put on seductive clothing to communicate "come hither." She was naturally attractive, with a disarmingly sweet personality.

Z was in the kitchen preparing our dinner. We hadn't been told there would be another guest but when we entered the kitchen we were introduced to X. He was about 6' 2", muscular, ruggedly handsome, and had a commanding presence. His comments communicated intelligence. When we were discussing politics, it became apparent that he read the NYT, the WSJ, and the Washington Post every morning. He was informed, articulate, and could dominate a debate if he chose to do so. And with his imposing size and build, he was the guy you would want on your side of a conflict if things went south in an alley. X and A seemed to really enjoy each other's comp[any, and Z didn't communicate any jealousy or discomfort about their mildly flirtatious behavior with each other.

Z told me that X was their close friend who was staying with them in their spare bedroom until he found a place of his own.

After dinner, Z and A gave us a tour of their house. X followed along. When they showed us their master bedroom, it was furnished with a king-sized bed. The room was decorated with erotic art.

Caroline lightheartedly quipped to A, "I'll bet you two have fun in this room."

A replied to Caroline in a playful tone, "Z and I have been married for about five years. Over time, I've learned a lot about what Z enjoys. In the beginning, his fantasies surprised me. But over time, we figured it out. Anyway, you're right, we have fun in this room."

Z stood quietly near the bedroom door, looking like he might blush. I noticed A and X briefly looking into each other's eyes, knowingly.

I had no idea then... but I do now. Z was a cuckold married to a woman who was willing to listen to, and to respond to his fantasies. I have little doubt that X spent time in their bed, enjoying the pleasure of being A's bull. Z may have been present, or he might have given them space to have sex alone in that bull-sized bed. X and A seemed to be perfectly matched for intense sex - a hotwife and a bull. Z presented as the quintessential cuckold.

I had no labels for these roles at that time. But what you see is what you see, labels or not. I lost track of Z at the end of that year. Perhaps he has been a member of this forum on OHW over the years. I hope Z, A, and X continued to enjoy their relationships, which seemed to work for all of them.

[The Owl]

Thoughts and reactions welcome. Have I penetrated the void with my signal...

[venus-can99]

Thoughts and reactions welcome. Have I penetrated the void with my signal...

Very interesting look back at the dinner as you have become wise can affix labels to Z, A and X. The signal has overcome the noise for sure
Did you have any further interactions with the trio?

[guitarman]

Once again, a wonderful recounting of events of your past. If we only knew then what we know now, how differently the outcome might have been.

[mfmfantasy50]

Another Twin Cities memory from 40+ years ago.

I had read Penthouse Letters about "wife watching" during that time but these events occurred long before the words "cuckold" "hotwife" and "bull" were common parlance. Looking back, I encountered all three characters in one home over dinner.

Thank goodness for Penthouse. They planted the seeds, gave them nourishment and exposed them to the sun; even if they didn’t provide a vocabulary describing it all in detail…

I trace many of my own personal sexual kinks and fetishes to those “shocking letters…”

Many of the letters were so outlandish at the time, that I questioned whether they were true stories!!!

Now, they’re mainstream!!!

Well, almost…

[mfmfantasy50]

Now it’s very REAL…

[shadowtantra]

You have indeed penetrated the void - better than the pent house letters that I grew up on!

[The Owl]

Now... which way to talke it?

1. My tale of trysts and dalliances with other women before I was divorce.
2. The divroce itself.
3. My wild sexual ride after the divorce. AKA being the Bull with some married women and single women, and then evolving into a cuckold.estions

Sugges?stions, desires?

[guitarman]

Having experienced both #1 and #2, I vote to hear more detail about #3. Nonetheless, I so enjoy your exceptional prose that any recounting of your trysts would be greatly appreciated.

[shadowtantra]

Hi Owl, I guess I would be interested in hearing about how the divorce does or does not play a role in your evolution as a Bull/ Cuckold? If there is no real connection then I go for 3. all of this is greatly appreciated! Thank you.

[PlzFuckMyHotwife]

Either would be great choices! Can't wait for the next episode!

[The Owl]

I'm back...

Regarding the divorce, there is really nothing erotic or unique about the story. Suffice it to say, Caroline decided she no longer wanted to remain in a marriage about which she had been so ambivalent for almost two decades.

We were on what I thought was going to be a romantic weekend trip. We were staying in a cabin on the shore of a lake. It was a starlit evening and we were sitting on the floor in front of a smoldering fire in the fireplace - flames licking upward and heat filling the room. I was naked. It was easy for Caroline to see that I was on my way to being fully aroused, sporting a mild chubby but not a full erection, yet. Caroline was still fully dressed.

Under those romantic circumstances, she calmly told me she wanted a divorce. My initial response was to quickly put on my clothes. I felt vulnerable and defenseless. We then had a calm conversation about her pronouncement. Clearly, she had been thinking about it a long time and had made up her mind well before the trip. She had finally mustered the courage to tell me. I knew she was serious, so we began the process of divorce, and all that it entails. End of divorce story.

For about two or three months after getting home from that fateful weekend, Caroline slept in her office and I slept in the bedroom. Then, I moved into a room that I rented in a large house where my best friend (Lex) and his wife (Lynn) lived. They regularly rented out three or four bedrooms in their house. My friend and his wife are about 10 years older than me. She is very religious. The day I moved in, she laid down the law, “No women.” She did not want me bringing home any dates to her house. If anybody was going to have sex in her house, they were going to be married first. Other than that very clear rule, Lynn was playful, supportive, and good company. I remained in their house for about six months while finding a house to purchase. During those months, I followed "Lynn’s Law.” I remained celibate during that time which was probably good for me as I was transitioning out of my marriage.

But when I moved into my own house, things changed. I quickly learned what a great wing man Lex could be. Lex, Lynn, and another friend I will call “Jim” all went to dinner at a restaurant in town. We had to sit at a table in the bar before we our table was ready for us in the dining area.

At the next four-top table in the bar, there was a beautiful slender blond – in her late 20s - seated by herself with two glasses of wine, as if there was somebody seated next to her. As I was sitting down in my chair, I turned to her and asked, “Are you using that second glass of wine as a foil to keep guys like me away?”

She smiled and said, “No, my mom is using the bathroom. Interesting idea though. I will keep your idea in mind in case I ever need it.”

Her mom returned to the table. The four of us briefly interacted with the mother and daughter. I learned that the blond’s name was “Tiffany” which fit her presentation perfectly. She was wearing tight hip-hugging pants and a short top, leaving her midriff fully exposed. Her stomach was firm and she sported a diamond in her pierced navel. Piercing were less common then than they are now. She looked hot. It was as if she had “sex” written all over her – in a most delightful way. Soon, the hostess approach Lex to tell him our table was ready. I expected nothing more to happen. I bid Tiffany adieu as we left the bar area.

A couple of minutes after we had settled into our dining table, Lex told me to look to my left. I looked toward the bar area and spotted Tiffany standing up with one arm raised high – her entire body wiggling with excitement as she waved toward me. She smiled and mouthed “thank you.” As she was standing and waving, I got an even better view of her runway-worthy body. She was not only beautiful, she was exotic. I was flummoxed and wondered if she might be waving at somebody else, perhaps Lex. I turned to Lex and he was sporting the smile of a Cheshire cat who had just finished eating a canary. I asked him, “What’s going on.”

Lex confessed, “You just bought Tiffany and her mom a second bottle of wine for their table.”

I had no idea Lex had slipped away and made arrangements with the waitress for me to buy her the wine. The cost was not an issue. The waitress played her role perfectly and explained to Tiffany that the gift was from me.

I turned and waved back at Tiffany and mouthed, “You’re welcome.”

As we were finishing dinner, Tiffany and her mom came to our table and thanked us for the wine. Tiffany was very direct with me and said, “We should get together sometime.”

I didn’t miss a beat and replied, “We should get together tonight.”

She playfully kicked my foot, smiled, and told me that her mom was driving and that she needed to leave because her mom wanted to go home.

I said, “I have my own car tonight. We're wrapping thing up here. I'm going to enjoy an after dinner drink at the Crystal Lounge. Do you know where that is?”

“Yes.”

“If you would like, have your mom drop you off there and I’ll give you a ride home.”

Cell phones were not used by most people at that time - land lines were the norm. I gave her my card and wrote my home number on the back.

Tiffany replied to my invitation, “We’ll see…” and left with her mom.

The four of us were soon leaving the restaurant. I drove myself to the Crystal Lounge and sat in a booth close to the three piece jazz band that was playing some classic tunes. Tiffany wasn't there and I doubted that she was going to show up. I ordered a drink and enjoyed the ambience.

A couple of songs into my martini, I was gazing at the saxophone to my left when I felt movement to my right. Tiffany had slipped into my booth and was sliding in next to me. We hugged each other and smiled. I asked, "How did you get here?"

"My mom gave me a ride home. But when we got there, she and I talked some more and we both agreed that I should meet you here. So, she drove back downtown. She waited in her car out front until I signaled her that I had found you. She's headed home and here I am... in a booth with you."

I ordered her a drink. She did most of the talking and I listened intently. She liked my sense of humor and playfully slapped my leg under the table in response to one of my responses to one of her tales. I put my arm on the back of the booth around her shoulders. My hand was close to her shoulder. After playfully slapping my thigh a second time, I lowered my hand and lightly caressed her shoulder. She kept her hand on my thigh. We turned our heads toward the musicians. Her fingers moved up and down slightly, in rhythm with the jazz - her hand felt improvisational. I move my arm and hand down and closer to her shoulders. I used my index finger to gently caress the skin where her neck met her shoulder. She seemed very comfortable with that level of touch. As the song ended, I turned to her and said, “Let’s go. I can show you my new house on the way home if you’d like.”

“I’d like that very much.” To punctuate her response, Tiffany firmly squeezed my thigh while locking her eyes with mine.

We slipped out of the booth and headed to my car. I drove and she rode through the heat of Friday night. I knew where I was headed but wasn’t sure where she was going with all of this. I hadn’t dated for many years and wondered whether she would play it cool during her first outing with me. I remembered the rules of dating when I was younger but had no idea what rules - if any - applied now.

As we entered the house, Tiffany said, “Nice house.”

She excused herself to use the bathroom. I lit the gas fireplace and turned on some dim mood lights.

Soon she was back, shoeless. She stepped up on the mantle, dangling her bare toes over the edge, with her back to the heat of the fire. I did not have a lot of art hung in the house yet. She playfully said, “You need some art. A black and white photo of me nude would go nicely over there.” I was trying to process what she was saying when she put her hands on my shoulders and lowered her lips to mine. She gave me a quick kiss and then moved her mouth closer to my ear while whispering, “You can touch me.”

(Anybody interested in hearing how the night unfolded from there? If so, to be continued...")