Okay, here goes. I am writing this story because I want to get this off my chest, I am too embarrassed and too scared to tell anyone about this. So, by way of this story, I am hoping to relieve my guilt.
My name is Cindy. I am divorced and live with my son. I am about 5’5”, and weight about 115. I am slim, with a small waist, small slightly curved ass and a small perky set of 34A breasts. I think my ass and breasts are my best features, but my mid-length blond curly hair has to be what gets the most attention. I try to tan, but so far have only acquired a slight tan due to a long work schedule and the normal time demands of being a single parent.
My son Josh is small and slim. He has sandy colored hair and has a light complexion. We have a great relationship and I have been thankful he never had rebellious years. I love him dearly….he is the one constant in my life.
Josh has always been very meek and shy, probably because of his small size and because I have raised him without a father. Josh’s father left us when Josh was about 6, and we have always survived fine without him. I had hoped that Josh’s father would play a part in his life, or that I could find someone that I could trust to explain adult things to Josh. I always dreaded when he would start to ask me those sexual type questions. I guess we are both shy.
Once a month, my friend Jessica and I take a night for just us girls and go out for dinner and drinks. We have done this for years, both of us hoping to find a man to fill the emptiness in both of our lives. Josh would stay at home alone watching television or playing video games. Occasionally Jessica’s son CJ would come over. I suspected that CJ was as socially awkward as Josh.
Jessica and I have talked to a lot of men over the years, but they always were after the same thing. It’s frustrating when you want to find someone to share your life, but only find men interested in sharing our beds. So, we repeat this each month, spending hours fixing our hair and trying to find just the right dress to wear. We always want to look beautiful and desirable, but not like someone that is going to spend the night with a stranger. We both want love and had vowed to not settle for anything else. This is obviously much easier said than done. Everyone has desires and longings. Masturbation has become a close friend…..as I suspect it has for Jessica too. We have hinted about it a few times, but never directly talked about it.
I am writing this on Sunday afternoon. Last night was our night out. I had spent about 2 hours getting ready. I have a bit of a ritual. I took a long hot bath, shaved my legs, underarms and trimmed my light brown haired pussy. I am not into the complete shaved look, so I always leave a medium sized landing strip. I always cover my freshly shaved pussy with a pair of sexy black panties. I complete the ensemble with a sexy lacy black bra and a mid-length black dress and a small amount of makeup. I am fortunate that I have great skin and need only the slightest makeup for nights like these. The “little black dress” clung to my body, showing off my figure and making me feel hopeful.
As I write this, I have to wonder why I go through so much trouble with the sexy underwear…and especially the shaving when I am positive I’m not going to bed with anyone. I guess it’s just nice to feel sexy even when you have no one. It does seem to give me confidence. Jessica rang the doorbell at about 7:15. She was dressed in a very similar dress, with the exception that her chosen color was red. Her long black hair was curled, as it always was, and she was wearing a matched set of earrings and a necklace. She was a bit more tanned than I was.
I hugged her in the doorway, grateful I was so lucky to have such a friend, but also a bit jealous of her developing tan. I made a mental note to try and spend more time in the coming weeks improving my tan.
The night started out wonderfully, as it always did. We had a great dinner, along with a few glasses of wine. We caught up on the latest developments in each other’s lives, even though we talked almost every day. This was just in case we missed anything or left out any details, I guess.
The rest of the night was disappointing as it always was. We went to a new place to dance, hoping to find a new crowd, and those ever elusive men that are looking for a relationship and not just sex. It seemed there was almost a never ending stream of men, eager to talk to me or Jessica…or both, but all with the same final interest in mind. We had a system….we tell them we are busy tonight and tomorrow, but if they would like to meet us for dinner on Monday then maybe we could make arrangements. Once the word “arrangements” was uttered, most men ran for the hills, knowing that meant a child or children. It works like a charm to avoid the men only interested in sex, but it has always left the two of us alone, lonely and questioning if we’ll ever find someone.
We wanted to drink some more, but it was a twenty mile drive back to my house. Given that this was yet another disappointing night, we decided to call it a night and go home. Jessica dropped me off at my house about 30 minutes later. I looked at my watch as I walked to the front door. It was 10:30. It didn’t feel like 10:30. The night had passed so quickly.
As I was about to enter the door, I remembered that Josh would be awake this early. I was depressed and I didn’t want to talk. As I fiddled with my keys, I dropped them onto the porch. This gave me an idea. I would feign being drunk and thereby not have to talk to Josh and answer a bunch of questions. I just wanted to go to bed and dream of a more exciting life. I realize this is not being the best mother in the world, but I really just wanted to think.
Josh opened the door as I stood up from picking up the keys. He gave me a whimsical look, as if he was trying to determine if I was intoxicated. Time to fake drunkenness. I smiled a goofy smile and patted his left shoulder with my right hand. “Hi Honey”, I said, as I walked past him, using my best acting to stagger through the foyer and into the den.
“Mom, are you drunk?”
“Just a whittle bit, Joshie, just a whittle bit.”
“Are you okay? Are you sick?”
Good grief, here I am trying to get out of talking to my son, and he is worried about my wellbeing. I felt like a terrible mom. But, I had started this, so I continued. Maybe, in hindsight, I oversold it.
“Joshie, baby,” I slurred, “I am going to my bed. Out the lights and go to bed by 10”. I knew of course that it was 10:30, but this was part of my attempt at being convincing. I staggered to my bedroom, closed the door, kicked off my shoes and slipped out of the little black dress. I removed my black bra and panties and tossed them to an empty chair. I found my favorite gown, Garfield on the front, and soft as a cotton ball. It had a bit of a low neckline and was almost long enough to reach my knees. I lay on the bed, face up, looking at the ceiling and pondering my fate.
I hoped to go to sleep, but my mind was racing with alternatives to what I was doing. Should I just give in and start sleeping around? Should I look for men on a dating website? All types of options rolled through my mind and I lay there, feeling sorry for myself but still enjoying laying the semi-lit room.
Thirty minutes passed and I still found myself awake. The light that I found relaxing just 30 minutes earlier now irritated me, contributing I reasoned to my inability to go to sleep. I was definitely not drunk, but I was in a lazy mood. I didn’t want to get out of bed and turn off the light; that was too much trouble. I was still lying face up on the bed. I placed a pillow on my face to block the light, too lazy to even roll over. That wasn’t working. I turned my head to the side, and opened my eyes to see my reflection in the mirror of my vanity through the tunnel created by the pillow on my face.
“Damn it, I’m cute,“ I reasoned.
Just as I was about to drag myself out of the bed and turn off the light, I head two knocks on my bedroom door, followed by my son’s voice, “Mom?”
I exhaled. He is a shy kid, and I was sure he just wanted to talk a bit before going to bed. I reasoned that I deserved a little bit of time at some point just to be alone and think.
I purposely didn’t answer him. A few seconds passed, followed again by a couple of knocks. “Mom? Mom? Are you awake?” I continued to lay motionless and quiet, and waited for him to give up and go to sleep.
As I lay there, the dilemma of the light reoccurred to me. Thirty or forty seconds passed and I had convinced myself that Josh had given up and went to bed. I thought of now getting out of bed and turning off that irritating light. I had closed my eyes when waiting for Josh to give up. As I again opened them, I saw from under my pillow that the light in the room had become brighter…from the bedroom door opening and allowing light in from the hallway.
“Mom, are you awake?”
Good grief, will this kid not give up? I again closed my eyes and waiting for him to go back to the living room. I reasoned that if he truly needed something, he would be yelling, not asking questions in his soft, mellow voice. I lay there, keeping up the ruse of being drunk, and now sleeping it off.
I remembered that my eyes were hidden from Josh’s view by the pillow. I carefully opened one eye and saw Josh’s reflection in the mirror as he stood by the side of my bed. I thought he must be trying to decide to wake me or let me sleep. Josh reached out to my shoulder closest to him and gently shook me, trying to wake me.
“Mom, are you asleep? Mom…..mom.” I lay perfectly still, somewhat impatiently waiting for him to give up.
I watched Josh’s reflection as he took a step toward the head of the bed, blocking my view of the mirror. As I peered out from under the pillow, I could only see his pajama shorts and a bit of his unclothed stomach. Josh has always tended to wear only his pajamas bottoms, and rarely his pajama top. He wasn’t talking or moving. He just stood there for at least a minute.
“Mom” (15 seconds passed)
“Mom” (30 seconds passed). I couldn’t get up after all this time…..he would know that I was pretending to be asleep. What would he think? Would he suspect I was trying to avoid him?
I continued to lay there quiet, wondering why this kid isn’t giving up. He obviously thinks I am in a deep sleep, so why doesn’t he stop saying “mom” and go to bed? His hand again shook my shoulder. Still peering under the pillow, I stared at his motionless body, confused by his actions. At least 30 more seconds passed before I saw him move. He twisted around toward the door and then back to facing me. As he got back to his position directly across from my peering eyes, I watched him put his right hand into his pajama bottoms and very obviously squeeze his visibly hard penis. I held back a shocked gasp as my eyes widened….
I tried to control the tensing of my body from seeing him begin to stroke his penis. I lay motionless, unsure what to do. A few seconds passed. Slowly, he removed his hand from his dick. Mentally reeling from what I just saw, I held my breath as I watched him now grab both sides of his pajamas, quietly sliding them gradually down to his knees. His 6” cock bounced upward as his pajamas move past he enlarged member. His dick pointed straight out. My face was no more than a foot from my son’s dick, engorged with blood and pointing directly toward my face.
I held back another gasp as he began to stroke himself again. His fist covered about half of his dick. He was moving it directly toward and then away from my face with each stroke. My pillow hid my now widely opened eyes. I could not believe what I was seeing. What would I do if he came? I lay there in disbelief as he continued to stroke his cock, and continuing to aim it directly at me. His pee hole opened and closed with each stroke, each time making me wonder if cum were about to spew out toward me. I watched as my mouth became dry with anticipation. He continued at the same speed for at least two minutes. All this time, my eyes were transfixed on the movement of his stroking fist toward my face.
To my great relief, he finally stopped. What the hell did I just see? Am I dreaming or did this just happened? My mind raced with ideas of whether this was a dream or reality. What could I do? I could not now miraculously wake up after all the attempts earlier of Josh trying to wake me up. I lay there quiet and motionless. I focused on a small amount of pre-cum on the tip of his dick as it glistened in the low light of the room. This was the first cock I had seen in over 5 years. Yes, I know it was my son’s cock, but I shamefully admit it was exciting.
It was then that I realized how quickly my heart had been pounding. Thankfully, it was slowing back to a normal speed. Josh had failed to realize it. As I slowly exhaled in an attempt to regain control of my breathing and heartbeat, I again felt Josh’s hand on my shoulder. If he says “Mom, Mom, Mom” again, that will be my opportunity to wake up.
This time, he didn’t say a word. Instead, he began to very gently and slowly rub my shoulder with his hand. This was such a nice, sweet loving gesture that I lost myself in the moment. Maybe the guilt of what he was doing had brought him back to his senses. I guessed that dick exposure was just a momentary urge that had passed.
I continued to be lost in thought. How the hell did this happen? It was then that I realized his hand had stopped rubbing my shoulder, but was still touching my shoulder, lying motionless above my left breast. Although I wasn’t moving, I felt myself freeze as Josh began to move his hand slowly from my shoulder downward. Was he going to cop a feel of my breast? What the hell was I going to do? Should I let him? Should I stop him? Did I need to let him so that he didn’t know I was pretending this entire time to be asleep?
He ever so softly began to rub the top of my breast, and then moved his hand carefully downward and cupped my teacup tit in his hand. He squeezed very slowly and gently. I then realized how hard my nipples were. Josh did also. He softly pinched my nipple, slowly twisting it just enough to send tingles down the full length of my body. I fought back the urge to moan or give any signal that I was truly awake.
He placed his hand again on my perky breast and began to lightly squeeze and fondle it. I could feel my pussy getting wet….my mind raced with thoughts of how the hell to get out of this situation.
Josh was always shy and quiet. He was never noticeably interested in girls. Maybe I had missed the signals all this time. Had he been fantasizing about me before tonight?
Josh’s hand moved from my breast…had he had enough for the night?
I then felt him moving the straps of my gown. He pulled the straps to the sides and started to lower the gown, he was going to expose my breasts for his full inspection. Seconds passed….I continued to feel the cotton soft material slowly move downward and my nipples pop free from under the gown. I could tell by the air on my chest that I was now fully exposed, with my son obviously inspecting them. I could feel my nipples swell at the thought. He had not moved from his position. I peered from under the pillow, wanting to see what he was doing.