My Sessions with Sammie Ch. 01

I spend time with Curtis's son!

Introduction:

I love young men. I love their innocence, energy, their lust for life. I love how excited they get and how hard they stay. I love the embarrassment they experience if, and when, they cum too quickly; and I love how, with the slightest encouragement, they are hard and ready to go again after they cum.

But most of all, I love knowing that they will never forget the intimacy of their encounters with me and that they will be better, more considerate lovers after spending some time with me. In a very real sense, it is a gift I can give to them as well as a gift to every woman with whom they will be intimate in the future.

This is the story of one recent encounter I had with a wonderful young man named Sammie. He was the son of a very dear and intimate friend of both my husband's and mine. Sammie had just celebrated his 18th birthday when I first met him.

An interesting and unique aspect of this story is that my experience with Sammie came with the encouragement and approval of my husband Jim, and at the request of Sammie's father, Curtis.

Curtis was my boss, and he had become a good friend of my husband, Jim, since they both shared me several months earlier. Yes, over the past few months, Jim and Curtis discovered that they shared a great many interests; including, on occasion, me.

Curtis was a tall, well built and strikingly good looking black man. At 6 ft. 3 inches, Curtis had broad shoulders, large muscular arms and a large, thick penis that stretched my core to its limits.

You can read about the first time Curtis and Jim both fucked me repeatedly in my true story entitled 'Cuffed, but no key'. It is a very detailed (and mostly true) account of how I allowed my boss to enter me while my husband watched.

Yes, for some unexplainable reason, since before we were married, over twenty years ago, Jim has enjoyed exposing me, and on occasion actually lending me, to other men. If you want to understand the details of how my life as a 'hot wife' first began, read my story 'Exposing Cindy: Spring Break'. It is the factually accurate story of how Jim guided me into a lifestyle I never expected, do not fully understand, but enjoy nonetheless.

After my initial encounter with Curtis last summer, Curtis, Jim and I would get together occasionally, for an evening of dining, flirting and dancing that would often lead to Jim inviting Curtis to our home for some late night petting and 'no holds barred' sexual abandon.

In addition to the wonderful sex with these two men, I also have a strong emotional bond with both of them. Curtis is far more than a 'fuck buddy'. He is a close and trusted friend whom I actually love. But his story is not really about Curtis, it is about an unexpected request he made of me.

This story begins at Christmas, 2013, several months after Curtis and I were unexpectedly thrust into each others' arms. Curtis, Jim and I were enjoying each others' company over a dinner.

It had been over a month since Jim, Curtis and I had been together. I wanted to see Curtis before my boys returned home from college, which would definitely impede my ability to entertain my boss, and my very close friend, in our home. I went to dinner fully expecting to make love to both of my dates that evening.

Because of the taboo nature of a woman dining with her husband and her African American lover together, we would typically eat at elegant restaurants across town, in an area known as Sugarland, far away from where I lived in the Woodland, north of Houston.

By dining across town, I felt I was reducing the risk of running into those in Jim's and my social circle who would be overly curious about the two men, one of whom was a large black man, with whom I was dining and with whom I was flirting so shamelessly, and whose hands seemed to be touching my arms, shoulders and legs as we talked and laughed together.

I do not think anyone needed to be overly astute to watch the interaction between Curtis, Jim and me to conclude that both men seemed to think I 'belonged' to each of them, to be shared between them. I love the attention I get when I am with the two of them.

There was something very sexy, and highly arousing to me, to be escorted by my husband of twenty years, and this large, strikingly handsome and powerfully built black man, to whom I allowed very intimate privileges. I would feel a level of wicked excitement walking into a nice restaurant between my two men, holding each of heir hands, knowing that I caught stares from other women who were wondering about the nature of the relationship between me and my two lovers. I caught stares of disapproval and envy as the ladies looked at me in a state of disbelief that I was brazenly flaunting my two men.

I often fantasized that these women, who looked at me with scorn, knew that I would have both men inside me before my evening was over. I enjoyed knowing that while outwardly disapproving of me; many of the women who did so were actually jealous of the thought that I would be driven to ecstasy by these two men later tonight.

I imagined that many of these women were bigots who would outwardly scorn at the thought of me taking a black lover, but deep inside envied me being ravaged but a huge black cock.

As I said above, over the past few months, Curtis and I had become far more than sexually charged lovers; we became close and intimate friends. We confided in each other about many things, as friends do. Over dinner that particular evening, Curtis was lamenting the social ineptness and awkwardness of his only son, Sammie. It seems that Sammie was a eighteen year old high school senior who was a good student and a fair athlete but incredibly awkward around girls. Curtis indicated that Sammie was beyond being shy; he was actually scared of the opposite sex.

Sammie lived most of the time with his mother, Curtis's ex-wife, but spend many weekends with Curtis. Curtis's ex-wife was going to be out of the country over Christmas, and Sammie and Curtis were going to spend the entire Christmas break together.

Curtis was having a hard time connecting with his son. He indicated over dinner that Sammie seemed to spend an inordinate amount of time in the shower or in his room on the computer; time which Curtis was certain was actually time that Sammie spent jacking off repeatedly.

"If that boy doesn't learn to at least talk with women, he is going to spend his entire life 'spanking his monkey' alone in his room," Curtis announced with a mixture of concern and disappointment.

I said that I personally found it cute and appealing that his eighteen year old was shy to the point of being a bit afraid of the opposite sex.

Jim seemed to agree with Curtis, "Yeah, he needs to move from the fantasy of masturbation to the reality of discovering a woman. He will be headed off to college in a few months, and he needs to break out of his shell." Jim paused, sipped his drink and then continued, "What he needs is a gentle, caring experienced woman to bring him out of his shell."

Both men smiled broadly and looked directly at me. Immediately, I knew where this was headed. "Oh no you don't. Don't put this on me," I protested. "That would just be too weird, too... I don't know, too something. I don't do fathers and sons."

Both Jim and Curtis roared in laughter. Curtis responded, "No one is suggesting a threesome with my son involved, Cindy. Even I am not that depraved. But you could spend some time with him, help him to get over his shyness, build up his confidence, and teach him a bit of how to act and what to do."

I quickly looked around the restaurant to see is anyone at the adjacent tables was eavesdropping in on our intimate conversation. We did not seem to be attracting any unusual attention from our neighbors. I sat there silently, formulating my arguments why this was simply a bad idea.

There was a long silence. Then Jim interjected, "Honey, if one of our boys was struggling like this, who would you want to teach them?; a prostitute?; or a teenage girl who might mock them or hurt them if they did not get it right at first?; or someone who could understand and guide them, and would do it with care and kindness?"

Jim and Curtis were right. If either of my two sons had been overly shy, I would want someone who cared and understood to guide them through their first encounter... actually someone like me.

"But it would just be too weird." I protested, repeating myself but deep inside the concept appealed to me.

We spent the next hour discussing and debating whether I would accept this assignment and if I did, just what would it entail? In actuality, I realized early on that I would comply with Jim's desire for me to do this; after all, I always complied with Jim's requests. I just needed a little convincing.

Jim and Curtis finally got me to agree to spend some time with Sammie in a casual, non-threatening setting. It would be up to me, and Sammie, what the lesson would involve.

"Just so we are clear, I am not committing to do anything except spend some time with him, right? What are the boundaries, Curtis? If the situation seems right, and he and I are both receptive, how far would you like me to go here? What are you comfortable with?" I asked.

"I trust your judgment. I am comfortable with you and Sammie exploring anything you two decide to explore. Let's just say, if you would want someone in a similar situation to you giving this experience to your son then I am OK with you and Sammie doing it," Curtis said with a confidence and trust that flattered me.

After taking a long sip of wine and giving the matter a little more thought, I suggested a plan. "Okay, tomorrow is Thursday. Sammie is off for Christmas break this week. My sons do not get done with finals and come home until early next week. So we should have some time where we would not be disturbed. If Sammie is receptive to spending the day with me tomorrow, we will see what happens. No promises."

My pulse began to quicken and my vagina began to moisten at the very thought of what I was agreeing to do tomorrow. I continued, "Curtis, if Sammie is up for this, I want you to drop him off in the morning, and pick him up tomorrow evening. I want to spend an entire day with him, uninterrupted. And in case he and I decide to enjoy some holiday cheer to relax him a bit, I do not want to worry about him driving home with any alcohol in his system. Deal?"

Curtis agreed and said he would talk to his son and get back with me that evening. I made it clear that I did not want a night of debauchery with Jim and Curtis the evening before I had my time with Sammie. I wanted to be well rested, squeaky clean and attractive for my young student tomorrow morning. It occurred to me that I had not had an orgasm since the previous Friday. I should be ready and responsive for my student tomorrow morning. I wanted to have a 'sexual edge' for my young student.

I smiled to myself, silently thinking that by talking me into this, Curtis and Jim had actually talked themselves out of fucking me that night. The irony amused me. They seemed to be willing to make that sacrifice for my young 'understudy'.

I kissed Curtis goodnight at the restaurant table. wrapping my arms around his neck and taking his tongue into my mouth, much to the interest of the people around us. I wanted Curtis to go home with a little but of a hard-on and think about me that evening. I also wanted the old biddies sitting at the adjacent table, and who seemed to be aghast at my interactions with these two men, to have something to talk about tomorrow. Jim and I said goodnight to Curtis, excused ourselves, and we headed across town towards home.

Around 10:30 p.m., Curtis called and told me that Sammie was very nervous about tomorrow, and he took some convincing, but he agreed to spend the day with me. Curtis would drop Sammie off at my house in the morning around 9:00 a.m., after Jim had left for work.

I could barely sleep in anticipation of my new student's arrival in the morning. I was in a state of arousal all evening, and it took all my willpower to keep from masturbating before going to sleep.

Chapter 1: Sammie gets his first lesson from a MILF:

I awoke before six. I heated the hot tub out back and then returned for a bath. I shaved all my 'parts', dried, powdered myself, put on my make-up, and selected my outfit. I wanted to look good, but I did not want to scare him; so I chose a pair of shear white bikini panties and silk pink gym shorts, and a white clingy top with no bra.

Looking in the mirror, I could see that I was still a very attractive woman. My perky breasts and small frame, combined with my short, sassy hairdo, and my large green eyes, gave me a younger, cheerleader appearance that belied my forty years.

I could see that my nipples were clearly evident. Plainly erect, the material did nothing to hide the contour of every slight bump of my nipple; the darkness of my nipple was evident as well. I was dressed provocatively, perhaps more provocatively than I intended, but not obscenely.

I fixed myself a Bloody Mary to help me relax until Curtis and Sammie showed up. I finished my drink, and was getting increasingly nervous when, at 9:20 a.m., they had not yet arrived. I was fixing myself a second Bloody Mary at 9:35 a.m. when the doorbell rang. I felt a lurch in my chest as my heart leaped in anticipation as walked to the front entryway.

I opened the door, let Curtis and his son enter and Curtis apologized for being late. "Someone was a little nervous this morning and took a little convincing to come over. But he is here now. Cindy, this is Sammie, my son."

I was then introduced to a tall, slender teenager, who reminded me of a young Will Smith. He was cute, shy, awkward and attractive and his shyness was adorable! Despite his shyness, and his inability to look me in the eye, he could not seem to keep himself from stealing glances of my erect nipples which were prominently displayed under the thin silky material of my top.

Curtis obviously noticed Sammie fixation with my bra-less breasts, he winked and smiled furtively at me. Curtis seemed very comfortable that his son would be fine in my loving, competent and compassionate care. Curtis quickly excused himself, indicating that he had a meeting at the office; leaving me and Sammie to get acquainted. Curtis indicated he would return between five and six in the evening. So, Sammie and I had eight hours or so to enjoy ourselves and to get acquainted. I wondered how Sammie would recall these next eight hours years from now, as he reflected back on them. I was pretty sure I would remember this day fondly. I was motivated to make sure he did as well.

I guided Sammie into the family room, where Jim, my husband, had built a nice fire in the fireplace for me before he left for work. I offered Sammie his choice of a Bloody Mary, some orange juice or coffee.

"What is a Bloody Mary?" he inquired.

I offered him a sip of mine, and the expression on his face was priceless. He did not like Bloody Mary's!

"I guess it is a bit of an acquired taste," I laughed. "Would you like some coffee? Or juice?"

"Juice would be nice. I don't drink coffee either."

I returned with a large glass of orange juice, and we visited, sitting on the couch in front of the fireplace. It was comfortable, relaxing and exciting, all at the same time as we made small talk, neither of us quite knowing how to broach the subject of sex. We talked about school, sports, his mom, his dad, where he might want to go to college, what he might want to study in college, girls at his school, the recent presidential election.

We chatted for more than thirty minutes. I finished my second Bloody Mary, made another, and offered Sammie a drink.

"You mean more orange juice?" he asked.

"That or something a bit stronger. Your dad indicated that since you were not driving, and since you are in safe hands, so to speak, it would be okay if you had a little drink. You do not have to, but it might help you relax a bit. I could put a little vodka in some orange juice for you. It is called a Screwdriver. You might like it."

Sammie agreed, and I made him his first Screwdriver. He tasted it and determined the taste was not too offensive. He drank this drink as though it was soda, and asked for another.

"OK, but take it easy on this next one. I want you to sip it, not gulp it down. You don't want to get sick and ruin our morning."

Sammie nodded agreement as though he understood.

We returned to the couch, and I decided to be direct and I asked, "So do you know why you are here today?"

Sammie's face turned bright red at the question. God I wanted to hug him he was so cute in his embarrassment. "I don't know. I guess so," he stammered. He suddenly could not look at me, his eyes were glued to the floor.

"Sammie, do not be embarrassed. It is okay. First, you do not have to do anything you do not want to. We can spend the day just hanging out and talking if you want, honest." I could feel my smile growing, revealing how very cute I thought this situation was. "Are you okay?"

He just nodded.

"I tell you what, let's spend some time talking about our bodies. You have a rare opportunity now. You can ask me anything you want about a woman's body, or more specifically, about my body, and I will tell you anything I can. I am giving you the keys to the kingdom so to speak. So what are you curious about?" I paused.

"I don't know..." was all he could muster.

"OK, if you won't ask me about my body, I will ask about yours. How often do you masturbate?" I figured I would break the ice one way or another.

Sammie's expression was a combination of horror and disbelief that I would ask about his masturbatory habits. "I don't masturbate," he said denying any culpability.

I chuckled loudly, "Now Sammie, you and I both know that is not true. If it is, you are the only person on the planet who doesn't. I masturbate. Everyone masturbates. It is normal and healthy. If you did not do it, there would be something wrong with you."

"You masturbate? How do girls masturbate?" he asked, suddenly, his interest clearly piqued.

I decided that if I wanted him to be open and honest, I needed to be open and honest with him. "Sometimes, I just rub my clitoris. I use my fingers and make small circles around my clitoris until I achieve a climax. It helps me go to sleep at night. Occasionally, when I am feeling particularly naughty, I insert a device inside me and use it to stimulate the inside of my vagina, while I am using my fingers on my clitoris."

"A device?"

"Yes, I have a couple of vibrators that are phallic shaped."

"Phallic shaped?"

"Phallic shaped, it means shaped like a penis. Would you like to see the vibrator I use the most?" I asked coyly and seductively. I knew his prurient interests now had taken over his shyness. My young student was far too curious to turn away from this opportunity now. Sammie nodded his head timidly.

"Wait here." I got up, went to my bedroom night stand and retrieve my favorite vibrating dildo. It was a little more than eight inches long and two inches wide, with a large prominent head and a series of thick veins running down the shaft. Aside from the fact that it was bright red and larger than 99% of the real male members I had encountered, it looked and felt fairly realistic.

I turned the vibrator on and it buzzed to life. I handed it to young Sammie for his inspection. The front of his pants was now tented up as he held a device that I had freely admitted to him had been buried deep inside my vagina recently.

As he studied the large phallus, he remarked with genuine concern, "Cindy, this is a lot bigger than I am."

"Oh Sammie, I am sorry. Yes, it is bigger than almost any man. That is sort of the point, if a woman is going to sacrifice the intimacy of a real man, she can get any size plastic dick that she wants, and it never gets soft, it never cums too quickly. All it demands is some new batteries every couple of months. But that is still a very poor substitute for a real man with a real functioning penis." I took a sip of my drink and Sammie followed suit, making a bit of a face as he sipped the vodka laced orange juice I had concocted for him. "OK, now I have told you how I do it. It is your turn. How do you masturbate?"