Mommy Trained Me WellbyPixxie©
The following story depicts a sexual mother – son relationship. All sexual activities and thoughts occur between adults at least 18 years of age.
My mother raised me all by herself. You might say that it's hard for a single woman to manage a rambunctious little boy, but I was always a well behaved child. Now that I look back on our life together, it's no miracle why.
My mom was always pretty. She managed her figure, wore flattering outfits and often went for youthful haircuts. When I was very little, I remember thinking that my mother was the "most beautiful mommy in the world" and I liked being near this beautiful woman.
As I got a little older, I noticed that she looked prettier on some days than others. When asked why she wasn't wearing much makeup or why she was not wearing one of her prettier dresses, she would tell me, "Mommy looks pretty when she's happy. Right now you're not making mommy happy. You want mommy to be happy, don't you?"
That was usually all it took to get me to do what she wanted. Mom was sly – finding this tactic effective, she would always wear two layers of clothes when we went out: an outer, frumpy layer for when I was bad (or just haven't proved that I was being good) and a prettier one underneath for when I was good. Being that the underlayer had to fit under her regular clothes, not to mention how hot it would get wearing two layers of clothes, the "pretty" outfit was often much more low cut. Miniskirts, strapless tops and short shorts were quite the norm when mom wanted to show how happy she was with me.
That was her style of dress no matter the time of day or season. Looking back, she must have looked like some kind of hooker ... with her small child in tow.
As I got older (18 of course), she would add "sexy outings" to her repertoire of rewards.
During the colder months, she would call me into her room before going out. "Baby, does mommy look nicer like this?" she would ask. She would pull her top tight from the back, emphasizing her lack of underwear. Her nipples would always be clearly noticeable and sometimes she would wear something shear enough that I would even be able to make out the darkness of them through the fabric. If I was being especially pleasant that day, she would even jiggle her breasts a little, playfully.
Of course spring and summer were another scenario altogether. Whereas in winter, you would have to look a little to see what mom was doing with her clothes – summer was more overt. A very special reward for me would be to go swimsuit shopping with her. Although I liked mommy in any swimsuit, our tastes would often gravitate towards bikinis. And while in public, she would never wear a thong with her son around – she could model them for me in the store.
Before you think that no store would allow a woman to model a thong for a man in plain view, most stores would allow a single parent to let their child (albeit an adult "child") into the changing area with them.
Behind the doors of the dressing room, mom would show me thongs and tiny string bikinis, suits with fabric so thin that they would leave nothing to the imagination and suits that were so tight that they looked painted on. All this, of course, with me being able to watch her change out of her clothes too.
It wasn't long before this modeling moved to the privacy of our home – where it became a frequent addition to our already scandalous activities. Almost every night, mom would ask me about my classes. If she deemed me "doing well in school," she would ask me into her bedroom and help pick out her outfit for the next day.
She would try on this one or that one, and sometimes even show me a new one that she just bought; it didn't matter whether or not she had shown me something sexy, presumably to wear into the office the next day, it was together time where I could watch my beautiful mommy undress frequently.
It was around that time that things became a little more physical. On an increasing basis, mom would come home from work, complaining about the tightness in her shoulders, and ask me to give her a little rub (this was above and beyond my normal reward system). She would then remove her bra from under her clothes, unbutton her top and slide it down enough to expose her shoulders. Thinking about mom's unfettered titties on the other side was enough to give me a boner. Being able to touch her skin and hearing her moan orgasmicly in return made me almost cream my pants. I always had to leave right away to relieve myself after massaging her.
Eventually, our daily after-work massage turned into weekend home spa days. The first day she proposed this idea, mom was undressing for me before her shower.
Mom was just making small talk. "I was talking to Mrs. Applebaum the other day; I heard you helped her out with her car battery," she said, stepping out of her skirt.
"Aw ma, it was easy. I knew right away what was wrong and they had a spare winter battery in the garage. It took, like twenty minutes."
"Still, it was a nice thing to do; otherwise, she would have to wait for Harold to get home and that would have taken him two hours." Mom had removed her slip and unbuttoned her blouse and was reaching for her bra hooks. "It was a nice thing to do," she emphasized, "Did she do anything for your trouble?"
"Just a Coke while I was working and she gave me a cookie afterwards."
She peeled her brasserie away. "Well, I'm proud of what you did son." Mom always made sure she told me what I was doing right. She paused as she slipped out of her panties.
"You know what would be real nice, hon?" she asked while getting her towel.
She turned to me, towel wrapped around her like a really short tube dress. "After my hot, steamy shower ... a nice, full back rub."
At the time, I thought, "cool, weekend back rub ... masturbate later." I never imagined the pleasures of what the phrase "full back rub" would entail.
We talked, like we usually do when she showers. She talked about local happenings; I watched her shapely silhouette through the rippled door.
Mom finished with the shower and toweled off in the stall. Emerging from the shower, mom untucked her towel wrap from her body, revealing herself to me like a blossoming flower. Mind you, I've seen her naked before, but never presented to me like she wanted me to see her like that. She had nice, full breasts that sat (not hung) nicely on her sturdy ribcage. Her figure was slim, yet curvy, and just a little bit motherly in the front. She had the grace of an oil painting and the exuberance of a cartoon.
She draped the towel on the floor in front of her and laid face-down on top of it; her round buttocks greeting me.
"Honey, get the baby oil out of the cabinet next to the sink, a body massage is so much nicer with baby oil," she purred. I did as she asked; what did I know about back rubs and who was I to argue with a sexy naked mother?
I squirted a little on my hands. "Don't be shy," she instructed, "the more the better." I began to squirt the oil directly on her back.
I started, kneeling between her legs, on her lower back. I imagined the bottle was my cock and I was jacking off on her ass. I squirted several shots before I figured that I should actually start rubbing it into her. I leaned forward, kneading her lower back, safely away from her curvy bottom.
She lifted her head up with a disturbed look on her face. "Baby, that doesn't feel so good. Your jeans are rubbing the inside of my thighs," she said with a pouty whine, "You'll have to take them off."
This was a dream come true, but it felt too awkward to be rubbing my mom, as close as we were becoming, with no pants on. I didn't have a hard-on yet, but I knew I was going to get one if I was going to be naked between my mother's legs.
Noting my hesitation, mom spoke up. "It's okay, I'm not looking." Her looking was the least of my problems. All the other cases where I was able to see mom naked or near naked, it was in the safety zone of my pants – pants that could hide the raging boner of a teenager. My briefs would provide no such protection.
"The pants will have to go or you need to stop with the back rub," she said simply. Her ultimatum was clear and I was forced to strip to my shorts and reveal my developing boner to my mom, who pretended not to notice.
"Isn't this nice?" she continued, "A relaxing Saturday spa day with mommy. Mommy likes it when you are good to her. Mommy likes to reward good, little boys."
I started the massage again. I did her lower back, but I let her guide me to where I needed to go and where I would not dare to go on my own. My hands travelled down her hips and around her thighs, orbiting her beautiful, spread ass. She humped the floor slightly and I noticed her pussy open up a little with a slight glisten in it that definitely wasn't baby oil.
I was disappointed when she asked me to move higher up her back; I was thoroughly enjoying opening mom's ass and looking at her pussy. I was massaging near her ribs when she gradually lured me higher and higher up her back until I was almost to her shoulders. I was about to get up from the discomfort of stretching across the entire length of my mother's body when she coaxed me to stay at it.
"Lean into the shoulders," she coaxed.
I found myself practically lying on top of my mother with my barely covered hard-on in the crack of her ass. Every move I made, I was afraid my cock would fall into her – popping out of my shorts and plunging into her pussy; this only made my dick harder and stick out at a more prominent angle within my briefs.
"Is this too uncomfortable," she stated innocently. I thought for sure that she was referring to my hard-on; it grazed her butt cheek more than once.
I began to sit up straight, relieved in a way, when she began to get up before me. Her ass pressed into my flagpole and I imagined that feeling was what it must be like to penetrate a woman. I only thought I was close to losing it when she scooted her butt into me, wiggling her ass into place between my legs. I looked down and saw my head poking out of my drawers and a huge drop of pre-cum forming at its tip. Noticing again my hesitation, she leaned back and asked for me to continue rubbing her shoulders.
Reluctantly, I did as she asked – not knowing what my mom must be thinking about me sticking my dripping cock up her ass and her pressing her whole naked body up to me. I kneaded her shoulders while my hips kept rhythm of their own accord.
"Forward," she asked. That placed my hands just above her mounds. There was just enough fat there to feel like I was getting some tit. My hands circled carefully around trying to grab as much of her breast as was polite.
Mom uttered a sexy moan and gently pulled my hands away. She turned around to face me and wrapped her legs around my hips.
"Mommy loves her good, little boy," she smiled as she pressed her naked, oiled form into me and gave me a loving hug in thanks. Her warm, wet pussy enveloped my shaft through my shorts as she pressed her body into me and I lost it completely.
Cum spurted up and out of my underwear. It landed on my leg, but also hit her on her stomach and thigh, dripping into her valley. This was the first time I ever had an orgasm in the presence of another person, not to mention it being caused by them. We both looked down at the lovely mess I had made.
My heart was racing and I ran. We never spoke of what happened.
I remember thinking that mom might actually enjoy getting massages as much as I enjoyed giving them. As for the "other stuff" that happened with the massage; I think mom felt like she had to give me something in return for such a nice backrub. As for what happened that other time; she made the backrubs worth their while, but she was careful that we were not both embarrassed in the process.
Late one Friday night, I came home late and hit the sack as soon as I got home. Mom was still in the shower. An hour later, there was a knock at my door.
"It's mom," said the voice, "can we talk?"
She didn't sound mad; so it wasn't about coming in late. Nothing bad happened recently to either of us that would require "a talk." I couldn't figure why she would want to have a talk so late at night.
Mom stepped in, wearing a long silken robe. It covered her completely from head to toe, but it was light enough to show off her figure. It made her look like royalty.
"I have a confession," she said with mock embarrassment, "I opened up your mail today. You got something from your school; you've got perfect marks in all your classes." She smiled and gave me a kiss.
"You must have been working so hard to get that," she said, standing. She let the belt of her robe slip, letting it open to me slightly. Underneath she had a sheer lace teddy that clung to every curve of her body. "Would you like me to get your shoulders?" Her arms rose for my shoulders, causing her robe to open more.
What she did was not so much of a massage as it was a thinly veiled excuse to run her hands across my chest and arms. Mom seemed very pleased with herself, doing something nice for her sweet son who was always the one giving the massages. Her hands drifted across my collarbone and frolicked around my chest as she hummed a vague tune; all the while she straddled my hips, grinding her pussy into my shorts.
I was already excited when I first caught glimpse of her teddy, now I was ready to go off. I was worried that I would have an embarrassing repeat of that other day. My hands, which were rubbing her legs, were now (subconsciously) pushing her away.
Sensing my discomfort, mom pulled my protesting hands from her legs and set them to my sides. Now that she was outed for her true intentions, she started riding my cock harder, bucking her hips now and then. Her breathing became labored, but steady. I tried to look her in the eye, but she was concentrating on our groins, passionately kissing each other. One of her arms reached back and cupped my balls, rolling them around. I watched her unfettered breasts bounce to her movements.
Like I said, I was already ready to go off; and it didn't take much time for me to come. I was still self-conscious about shooting off in front of my mom, so I tried to hold it back a little; this only served to make me come harder. My cock throbbed like a greyhound's heart, pumping its juice into my shorts.
"If my smart little boy cleans himself up, he may snuggle with me later on," she said, leaving me with my mess.
I couldn't believe that my mom intentionally jacked me off with her pussy (I was still reeling from the after-effects). My mom intentionally wore an outfit, solely for my benefit. My mom intentionally grabbed my balls and rode my cock. My mom intentionally rubbed her mound into my cock until I came.
Up until that point, I had thought only about myself. I watched mommy undress; I never thought she might be undressing for me. I was rubbing mommy's body; mommy was letting me feel her up. Mom gave me a naked hug. Mom gave me a sexy massage. Mom dry-humped me until I came. Whereas before I had seen her as my "sexy mommy," I now saw her as a separate person who wanted me to be happy.
After that incident, I noticed the criteria for rewards getting lower and lower. Cooking dinner for her, fixing the sink, finishing school projects ahead of time; these were all subjects for reward. Not all of those rewards consisted of me orgasming (at least not on the spot), but they all involved her body somehow rubbing against my cock. Nothing since that moment had we done anything so overt.
I found myself getting hornier and hornier. I wanted to have sex with my mother; but there was no plausible way, even with the physical relationship that we had, of broaching the subject of a son wanting to have intercourse with his mother.
It was getting the end of the academic school year and I found myself getting tied up with doing well in all my classes. For the benefit of my grades, I put all personal thoughts about my mother out of my head. Nothing overly physical or distracting happened during that time. Mom understood, but still encouraged me with hugs and kisses.
In particular, I was doing some extra work with one professor which produced some amazing results; so much so that the college wanted to recognize me for my work at that year's graduation (for those of you that are not paying attention, I am not graduating yet). Mom was excited beyond words for me.
"We must celebrate. Why don't we go to that nice restaurant that we really like?"
I have to admit, my expectations for celebrating were a little higher; I hadn't even masturbated at all in that time. "I was thinking of something else," I said sheepishly.
Mom put on a face of mock outrage. "You naughty boy. If I wasn't so proud of you, I'd beat you senseless," she teased. "What would you like?" she asked, "A special massage?"
I still couldn't ask mom if I could actually put my dick into her. I thought about the most I could ask for that my courage would allow. "Mom, can I lay on top of you – like I do when I rub your shoulders – except this time, can I do it without my shorts?"
Mom was legitimately shocked; I had, in essence, asked to have mock-sex with her.
Mom thought about it. "You're asking to lie naked on your mommy?" She looked troubled. "We'll see ..."
Dammit. "We'll see" is code for "I don't think so."
I was dejected, but fortunately I had other things to occupy my mind over the next few weeks. I kept myself busy and mom – I think she was starting to feel guilty for letting me down after all my hard work.
The night before the ceremony, mom came by to kiss me good night. She was wearing that wonderful silken robe that I like, but tied closed. "About tomorrow," she began, "we'll do something nice for your special day." That was that.
Something nice: Probably Cheesecake Factory or Olive Garden; might as well be Chuck E. Cheese.
Come time for the ceremony, mom was in tears. She had never been to a graduation ceremony before; it didn't matter that I wasn't graduating. She was crying so much that she couldn't even voice her congratulations to me. There was one moment, when she was trying to hold back the tears, that she looked me in the eye – like she was trying to read me.
"I can't believe that they would ask you to be in their ceremony," she was saying as we drove away, "and you're an underclassman. You, my boy, worked hard for it ... you deserved every bit."
We talked so much that I didn't notice that we weren't headed for the restaurant at all; in fact, we had just drove home.
"Why did we go home?" I asked, confused (and a little dense), "What about the restaurant?"
"Let's have a little something special at home," she said, not revealing anything.
She pushed me down on the floor as soon as we stepped into the house. She stripped me out of my shirt and started unbuttoning her top. I started to ask her what's going on, but she stopped me with her lips.
Undressed, I could see that she was wearing the most amazing camisole and panty that I had ever seen. It was satiny and antique pearl in color. The collar was Italian lace and just barely covered the top of her breasts, which hung down towards me enticingly.
Mom helped me out of the rest of my clothes, including my shorts. She lay on top of me, her heavy breathing right in my face. I started to say something and again, she stopped me with her mouth.
We kissed passionately like we had never done before. Mom slid her panties off and softly rubs her fur into my rapidly growing cock.
"I'm so proud of my boy. Mommy's so very proud of you." She started crying again.
Mom pulled away and sat up, my dick still at her pussy.
"Umm, did you wash the dishes today?" Her tone of voice changed, like she was trying to remember something.