Introduction: I love young men. I love their innocence, their 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 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 and to every woman with whom they will be intimate.
This is the story of one recent encounter I had with a wonderful young man named Stephen. Although I had known Stephen since he was a boy, he had just turned sixteen when this story begins.
But before I begin my tale, I need to tell you, the reader, an interesting and unique aspect of this story is that my experience with Stephen came with the encouragement and approval of my husband, Jim.
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.
So, in a very real sense, my husband ‘insisted’ that I tease, and ‘educate’ our young neighbor.
This story begins at Christmas, 2016
Chapter 1: “Stephen’s morning wood”
When our neighbors, Karen and Roger, got an opportunity for a six-month temporary assignment in Milan, Italy, they were presented with a tough choice.
This was a once in a lifetime opportunity for them to experience Europe; however, their only son, Stephen, was in his junior year in high school, and removing him from his school would be extremely disruptive to his sports and academics.
Karen thought out loud to me, “In a couple of years, when Stephen was away at college the timing would have been perfect. But I am afraid we are going to have to turn down this opportunity rather than disrupt Stephen’s junior year.”
After just a moment’s thought, I suggested, “Why don’t you let Stephen stay with Jim and me until the end of the school year, and then he can join you and Roger in Milan?”
Stephen was a polite, well-mannered sixteen-year-old. He was active in sports, playing football and basketball, and was a good student. I had known him since he was a toddler, and I was completely comfortable he would be no trouble. He was a good looking athletic young man, who was a bit on the shy side. I knew the girls would be crazy about him once he gained a bit more confidence.
As his thirty-eight-year-old neighbor, I found his shyness to be a very endearing quality.
Karen thought for a moment, and responded, “Oh, I could not ask you and Jim to take on that responsibility. That is just too much.”
“Nonsense,” I responded. “We have plenty of room with our own boys away at college. And Stephen is no trouble to anyone. He can come visit you over spring break and at the end of the school year. Seriously, at least ask him if he would be up for it. He could have the downstairs guest bedroom and bath that Jim set up in the basement. To be honest, I would enjoy having him around. He is good company. And with Jim traveling as much as he does, I am home alone quite often anyway.”
“Good company? He hardly speaks at home!” Karen laughed. “But if you are sure about this, I will discuss it with Roger and Stephen as see what they say.”
The next day, Karen informed me that if Jim and I were sure about this, they would like to take us up on the offer. Stephen was set to move into our basement guest room in mid-January, 2017, right after our own sons returned to college from their winter break.
The basement had a queen-sized bed, and bathroom with a shower stall, and an assortment of weight lifting equipment that Jim and my own boys used when they were at home. There was also an old couch and TV set. Really, it was a pretty nice little ‘apartment’ for a sixteen-year-old boy.
We gave Stephen a key to the house. He would continue to park his vehicle in his parents’ driveway across the street so their home would not appear vacant. His parents established his curfews: 9:00 p.m. on school nights, midnight on Friday and Saturday.
Jim’s and my rules were pretty non-existent; however, Jim did not want Stephen using the weight lifting equipment by himself without a spotter (for safety reasons). If he wanted to lift, he needed to get either Jim, or me, to spot him. This was the same rule we had for our boys when they were home, except they could spot each other.
The first week went by without incident. Stephen would get home after basketball practice, around 6:00 p.m., eat and retire downstairs to do homework and/or watch TV. He got himself up each morning, fixed himself some breakfast, and left for school with little or no prompting from Jim or me. As I expected, he was no trouble.
One morning, the second week Stephen was with us, I noticed that he was not up at his usual time.
I ventured downstairs to check on him, and found him still in bed, asleep wearing only a pair of boxers, with a set of headphones on. He was tangled in the covers like he had had a wrestling match in his sleep. But what really caught my attention was the morning erection Stephen was sporting. Still fast asleep, his right hand was inside his boxers, holding his beautifully erect penis loosely. I assume the headphones kept him from hearing me approach, even as I called his name quietly.
I stood there mesmerized by the erotic beauty of this scene. The sight of this good looking, virile young man lying there with an impressive rigid circumcised penis forced my mind to wander to places I had never intended. His erection peered above the waistband of his shorts by at least three inches. It had a slight purple tint around the mushroom-shaped head. I stared for several moments before forcing myself back to reality.
I could not help the warm twinge I felt in my crotch as I stared shamelessly. But after all, despite the erotic image, Stephen was the son of one of my best friends, and I needed to put these thoughts out of my head.
I reached down and gently touched his arm slightly above where it disappeared inside his boxers, and shook him awake. In a matter of seconds, Stephen bolted awake and suddenly realized his level of exposure. It was adorable how he quickly flipped over on his stomach to hide his rigid penis from me, while simultaneously pulling off his headphones.
“Stephen, I think you have overslept. It is almost 7:30,” I said as casually as I could, with no indication that I was very aware of his ‘morning wood’ predicament.
“Oh, I am sorry, Miss Cindy. I don’t know how it happened.”
But he remained lying on his stomach, obviously embarrassed of me seeing his stiffness.
I decided to not play with the boy’s head anymore, and began to leave. “Well hurry up, you will be late. And your parents do expect me to make sure you actually attend class every day.”
I resisted the urge to call out one of my father’s favorite wake-up calls to my older brothers: ‘Drop your cocks and grab your sox, boys!’
A few minutes later, he bolted through the door, without breakfast, heading to school. But the image of that sixteen-year-old erect cock would not leave my mind all day long. Around 11:00, I went to my bedroom and masturbated to “take the edge off” a bit, as the sights of that morning still had me fairly aroused.
That evening when Stephen came in from basketball practice, wearing his sweats, he tried to walk directly downstairs without even making eye contact. I knew he was embarrassed by our brief encounter that morning. Jim was not due home for about forty-five minutes, so I had some time to talk with Stephen.
“Stephen, is everything okay?”
“Yes, Miss Cindy. I am just a little tired.”
“Are you sure? You seem a little ‘distant’ this evening.”
He stood there for just a moment, thinking before speaking.
“I wasn’t doing what you think I was doing this morning,” he said as he studied the floor in front of him, unwilling or unable to look at me.
I could not suppress a laugh.
“Oh Stephen, you are adorable.”
This comment seemed to only add to his embarrassment as his face shone a bright crimson. I decided I really did need to relieve his anxiety over this.
“Stephen, I do not think you were doing anything other than sleeping. You are a normal, healthy young man. And normal, healthy young men get erections in their sleep. There is absolutely nothing to be ashamed of.”
I paused and then continued, “And even if you were ‘doing something’, which I know you were not, that would be normal and healthy as well. All boys your age masturbate. For that matter, boys and girls of all ages masturbate. It is normal and healthy.”
And as I spoke, I noticed, with some amazement, the a slight but growing tent in his sweatpants. He was growing erect while we spoke.
Without thinking, I smiled and said, “It appears that you are starting to feel pretty normal and healthy right now,” as I glanced at his crotch.
“Oh, Miss Cindy, I am so sorry. I didn’t mean anything.”
He turned and started to bolt downstairs.
“Stephen, come back here. You did not ‘do anything wrong’. You have normal physical reactions.”
He stood there trying to hide the tent in the front of his pants. I could not deny that I found this whole unplanned situation very arousing.
“Miss Cindy, I am sorry. I don’t mean any disrespect.”
“Stephen, it is not disrespectful; it is very flattering to any woman when her presence causes him to become aroused.”
I paused for a moment, to let this sink in.
“I try not to let this happen, but sometimes I can’t control it.”
Stephen was obviously struggling with the sexual awakening he was experiencing. And he obviously was fairly naïve about the normal reactions of an adolescent male.
“It seems like it has a mind of its own.”
“Stephen, this really only shows you are normal and healthy. If this wasn’t happening to you with some regularity, I’d be worried. It is just that when a man becomes aroused, it is a little more ‘evident’ than when a woman becomes aroused; which may cause you some embarrassment on occasion. But women have the same reactions, it is just a bit less obvious when we do. To be honest, this conversation is affecting me the same way it affects you.”
Stephen looked puzzled, and after a painful silence he worked up the nerve to ask, “How do women get aroused?”
I wasn’t sure whether Stephen’s ignorance of a woman’s sexual response was real or feigned, but I decided that being honest and factual was the best course right now.
“Women get aroused when their vaginas become very moist, actually wet, and their vulvas begin to open up in a way that would allow them to accept the male penis, their nipples and their clitoris become erect and sensitive.”
He stood there still hiding his erection, which was quite obvious at this point, and he looked puzzled, but interested in hearing more. I was very aware of my pulse in my clitoris, and I knew my nipples were pressing through my bra and plainly visible against the cotton material of my shirt. I could not help recalling the beautiful erection I had witnessed this morning.
“Stephen, this conversation – and your reaction – is causing a similar physical response in me. You can see my nipples are erect. I am also having a response ‘elsewhere’.”
Stephen looked puzzled.
So, I continued, “Stephen, just as this conversation has you aroused, my clitoris is erect and my vagina is moist…leaking, in fact. I find this situation, and your arousal very exciting. In fact, I am going to go into my bedroom and say ‘hello to little Cindy’ before dinner. And I suggest you go downstairs and ‘take the edge off little Stephen’ too.”
I smiled, stood up, walked by Stephen, glanced at his bulging sweatpants, and said, “Yes, you are a very normal and healthy young man indeed.”
He was blushing a deep crimson shade, but had relaxed a bit and was not hiding his erection from my view quite as much as before.
I went into my bedroom and quickly brought myself to orgasm before dinner. It did not take long; this whole scene had me very aroused.
When I came out to the kitchen, Stephen was still downstairs. I assume he was taking care of himself in a similar fashion. The fact that I had played even a slight role in this sixteen-year-old’s masturbation this evening was strangely appealing to me. But I had no intention of taking this interaction any further.
Jim came home about thirty minutes later, and I called Stephen up for dinner. I could not help but smile at “our little secret”. Stephen seemed to avoid eye contact with me during dinner. Clearly, he was unsure how to interact with a thirty-eight-year-old woman who had recently told him of her plans to masturbate.
I shared my “experience” with Jim that evening, and as I would have predicted, he too found it terribly arousing. He pretended to be Stephen as he entered me that night, calling me ‘Miss Cindy’ as he spilled his seed inside me. I enjoyed the fantasy.
The next morning, he instructed me to not wear a bra when I was home this afternoon with Stephen. I protested but knew I would comply with my husband’s instructions; after all, I always did comply.
As you know from my previous (true) stories, I am a shameless exhibitionist who enjoys teasing men with my husband’s approval and encouragement. And even though I was not too terribly exposed wearing a pair of black satin gym shorts and a white sleeveless cotton workout shirt without a bra, I was aroused waiting for Stephen and my nipples were erect and quite visible under the thin cotton fabric.
When Stephen came in, I insisted on talking to him about his day, his school work, basketball practice; basically, anything that forced him to interact with me while my hard nipples taunted him from under the white cotton material.
I was quite amused as he tried not to stare at my perky breasts, but he just could not resist trying to steal a glance without being too obvious. It had been a long time since I had felt this attractive, this desirable or this powerful. And as you would expect, he became erect quickly while we talked and flirted.
Yes, I was going to enjoy teasing this handsome and virile young man for the next several months. However, I had no intention of ever becoming physically intimate with him. But I would enjoy keeping him in a constant state of arousal and making sure I was the source of his masturbatory fantasies.
I did not change my outfit when Jim got home, and we ate dinner as one happy little family, with my breasts receiving considerable attention from the watchful eyes of both of these two men: my husband and my sixteen-year-old houseguest. I was enjoying every moment of this.
For the next few days, the routine was the same: I would wear an outfit that was revealing, but not obscene. My braless breasts were constantly on display under some thin, clingy material. Stephen got more and more comfortable enjoying my perky figure and my pert nipples. Stephen quickly realized that I would not chastise him for stealing an extended glance. In fact, Stephen quickly realized that I enjoyed his glances, and he became less subtle.
On Friday of Stephen’s second week with us, I got an idea to tease him a bit more. The weather was overcast, and rain was predicted. I had washed some of my most intimate and revealing lingerie and hung them to dry in the backyard.
When Stephen came in, I was on the phone, and the wind was starting to kick up a bit in a prelude to an east Texas rainstorm. I interrupted my phone conversation just long enough to ask, “Stephen, would you be a dear and bring in my laundry for me before it rains? I need to finish this phone call or I would do it myself. Just fold them and place them in the basket by the back door.”
And I returned to my phone conversation without waiting for an answer.
Hanging in the backyard were sheer bras and panties, lacy push-up bras, sheer teddies, both with and without garters, a sheer see-through baby doll nightie. It was a smorgasbord of teenage boys’ fantasies. Stephen would have his hands all over my underwear, only I would not be wearing them at the time.
I watched with keen interest from the kitchen as he struggled to fold the intimate apparel. I suspected I would be a part of his masturbatory fantasies tonight.
Saturday morning, things took a bit of an unexpected turn. As Jim was getting ready to leave for his golf outing with his buddies, Stephen asked him if it was okay if he used the weight equipment in the basement.
“Certainly, Stephen. But you need to get Cindy to spot you while you are lifting.”
Jim smiled at me.
“If you ask her real nicely, I bet you can talk her into it.”
I was wearing a robe that came down to my mid-thigh. Underneath, I had a sleeveless shirt and a pair of panties.
Stephen looked over and asked, “Miss Cindy, would you be willing to spot me sometime this morning?”
“I would be happy to. When do you want to lift?”
“Any time you are ready.”
“Okay. Let me get Jim out the door and I will be right down. Why don’t you go downstairs and stretch and warm up?”
I caught Jim smiling at this situation.
After Stephen went downstairs, Jim whispered to me, “Don’t put anything else on. Spot him in your nightshirt and panties.”
I looked at Jim, questioning, but he gave me the look telling me this is what he wanted me to do. And dutifully, I knew I would do just that. Jim left and I headed down the stairs to the basement, my pulse racing and my nipples erect. Stephen had set up the flat bench with two large plates on the barbell. He was already lying on the bench under the bar.
I walked over and removed my robe, saying simply, “I don’t need this getting in the way. Do you need a lift-off?”
As I stood there, my shirt was long enough to come down just past my panties, but I knew once I stepped up and spotted him, slightly straddling his head, he would be looking directly at the moistening gusset of my panties.
“No. I think I have this.”
I stepped up, in position to assist him if needed, straddling his head slightly. Because I am moderate height, about 5 feet 7 inches, my pantied crotch was very close to Stephen’s head and face. This situation had me lubricating rapidly, and I wondered how evident the moisture in my panties’ crotch was to Stephen.
I wondered if he could smell my aroused scent.
I looked down and saw the crotch of his gym shorts rising and pulsing. He was as aroused as I was, and it showed. The sexual tension was incredible. Stephen did one set with the barbell. God, he looked so sexy, his muscles straining as he lifted and his erection pushing up his gym shorts.
Once he completed the set, he racked the weights with my assistance and sat up.
“You are in good shape. That was a good set,” I said, trying to sound as nonchalant as I could.
My hands were still resting on the bar, as Stephen got a peculiar look on his face.
After a moment of silence, he slowly reached over and ran his hand up my inner thigh. I froze.
“Stephen, you must not do that.” I did not actually try to physically stop him, though.
“Miss Cindy, I just want to see if you are aroused like I am.”
His hand slowly slid further up my leg to the gusset of my pale green cotton panties. He ran his fingers gently over the outside of my vulva. When his fingers slid across my erect clit, I closed my eyes as a slight moan escaped my lips.
I panted again, my breathing quickly becoming labored, “Stephen, we really can’t do this…”
He had found the crease of my vagina and was slowly sliding his finger up and down my very wet crack, gently teasing my erect clit. Part of me wanted to stop him, but I simply could not bring myself to do so. I found myself involuntary rocking my hips slightly as Stephen stroked me into a state of arousal.
I was still balancing myself on the barbell when Stephen started to pull the leg of my panties open and run his fingers inside my panties, stroking my very wet vagina ‘skin-to-skin’.
“Oh God, Stephen, we shouldn’t be doing this. You need to stop.”
Stephen had his fingers at the opening of my vulva. I knew I was losing all control. As he started to insert one, then two fingers inside me, I squatted down to allow him full access, as I told him to stop.
“Stephen, please… Oh God…”
I was starting to babble incoherently.
I was wet enough and aroused enough that he was able to slide two fingers deep inside me. He curled his fingers back towards him, massaging the front wall of my uterus, right at my g-spot.
“Stephen, you need to stop. You are going to make me cum. I can’t help it, if you don’t stop, I am going to cum.”
I was bending my legs, spreading my knees as I balanced myself against the barbell. I was rocking my hips in time with his deep internal massage, forcing his fingers as deep inside me as I could.
Then it hit me: the first orgasmic wave. Stephen was abusing my vagina with his fingers, finger fucking me as deeply and violently as he could as wave after wave of pleasure rocked across my abdomen.
I typically have a difficult time achieving orgasm, and I almost never have more than one orgasm. But I was experiencing a powerful and long multiple orgasm with Stephen’s fist buried inside me. I thought I was going to either pass out or collapse.
“Stephen, you need to let me come down. I need to stop. I can’t take it anymore.”
And I grabbed his hand and pushed it from me.
I stood there, trying to collect my thoughts, trying to recover. Stephen stood up, took my hand and led me to sit on the bench where he had been moments before. Standing in front of me, Stephen lowered his gym shorts and boxers together, stepping out of them. His rigid penis stood straight up in front of him, about eye-level with me.
“Stephen, I can’t do that. We should not have done any of this.”
“Miss Cindy, please. I need you to take care of me. I am so hard it hurts,” Stephen said as he reached over, took my hand and placed it on his rigid cock. “Please, Miss Cindy, please help me.”
I slowly closed my fist around his shaft, slowly moving my hand up and down as he rocked his hips.
“I should not be doing this. This is just wrong.” But I continued to pump my fist and I stimulated his entire penis.
Stephen reached over and took my head as he pushed his cock towards my face. I looked at him and hesitated, but then relented, kissing the head of his cock gently before opening my mouth and accepting the head just past my lips. Stephen moaned and thrust himself forward, trying to push deeper into my mouth. I continued to pump with my hand, picking up the pace.
Stephen’s movements became more frantic; I felt his cock grow slightly and begin to pulse. Stephen was trying to hold my head in place as his cock pulsed repeatedly, and I got the first taste of his semen. I pulled my head backwards, freeing his cock, and pumped him furiously.
Suddenly, the first thick, long string of warm, white semen shot from the open slit on the head of his penis high into the air in front of me, and landed on my bare shoulder and shirt. The force at which the semen ejaculated from my youthful lover was impressive. It had been more than a decade since I saw a teenager ejaculate, and I was impressed with his power and force.
The scent of his semen was also very arousing. An instant later, the second long string erupted from his penis, this time landing in my hair and on the side of my face. Rather than being repulsed, I was intrigued and excited by Stephen’s series of ejaculations.
And then another, smaller, less powerful string erupted, falling on my lap and legs. I leaned forward and kissed the head of his throbbing erection but did not open my mouth. Something prevented me from ingesting his semen, but I did enjoy the wonderful aroma of the teenage semen.
Stephen’s movements slowed considerably now and he seemed a little weak-kneed.
“Is that better, Stephen? Is that what you needed?”
“Oh God, yes. That was wonderful,” he said as his chest continued to heave, and his penis remained erect in front of me, pulsing periodically upward.
I was tempted to take him inside of me, to feel his erection inside me, but I resisted the temptation, realizing that we had already committed a grave enough sin today. Besides, I was not sure how Jim would feel about all this.
“Well, we should not have done any of this. Goodness, Stephen, you made quite a mess over me.”
I scooped up some of the semen from my leg and brought it to my nose to inhale the scent.
“I need to go get cleaned up a bit. You have a wonderful cock. You are going to make some girl very, very happy someday.”
I leaned forward and kissed the head of his cock one last time, and as I pulled away, a small string of his semen hung from my lips.
Before getting up, covered in his semen, I looked up at him and could not resist a joke of sorts. With a slight trace of his cum hanging from my lips, I smiled and said, “I guess I don’t get a thank-you kiss, huh?”
Stephen smiled back and merely said, “Perhaps later?”
