A Mother's Lessons

A story of lessons for a son from his sexy mother continue. This chapter is about prostate and anal play with some light cbt so if not your cup of tea you may want to skip to Ch. 05.

Chapter 4

After being fully satisfied and spent I dozed off with my mother naked against my body. I had the most amazing dreams and yet even in my dreams I could not believe this was happening to me. I lost my virginity to the sexiest woman I had ever known and all in one night I had both given and received incredible oral and both made love and fucked a woman of my fantasies. Then all of a sudden my dreams seemed to be getting more and more real and I stirred awake.

As my eyes slowly opened and some light was pouring in between the curtains I felt that my mother was no longer next to me in bed, but also realized why I felt so incredible. She was between my legs sucking on me! My cock was solid steel and after I came twice just last night I felt confidant that I could last quite awhile enjoying this feeling. Well at least I thought I could, but even after one night with her I should have known she would find a new way to drive me over the edge.

As she moaned fully deep throating me she grabbed my balls and began alternating the intensity of her grip. As she came back up and swirled her tongue around my head she loosened her grip and as she fully took my eight inches down her throat she squeezed my balls so hard I would gasp from the pain and the pleasure. It felt SO good! As she came up again she gasped for air and her eyes locked into mine.

"I see my baby boy is awake, do you like what mommy is doing to you? Do you like waking up to my hungry sexual appetite? These balls need to get so full and I need you to feed your mommy so much cum!"

As she stared into my eyes as I slowly woke up I was then immediately slapped awake, literally, as I did not expect it at all as she slapped my balls! Gasping in pain she began rubbing them so softly and almost cooing at me. "Oh my baby boy, these balls are all mine now to do what I want to them. After last night we have a lot more to explore I hope you are ready for it all." She then slapped them again even harder than the first time! As I cried out I went to grab them and she immediately slapped my hands away as she caressed them. I was shocked, but it felt incredible the back and forth of intense pain and her soothing touch. The crazy part was I found myself wanting another one and it was almost as if she could see that in my eyes.

"Your mommy has so much more to teach you, but I can already see you are ready to be so kinky with me. I told you I can be your sexy mistress and you will do all that I say, but it also means I will do everything to you that turns me on. Do you agree that it is my pleasure that matters? Can you make sure mommy's pleasure comes first?"

As I open my mouth to answer all that came out was another yell as she slapped them again, twice! It felt so overwhelming good and made even better by the pure desire on her face. I never wanted that facial expression to change and wanted to provide for her pleasure for a very long time to come.

"Well my baby boy your balls have swelled up nicely and filled with even more cum for your hungry mommy. I bet you never thought you would like pain that much and neither did I at first. I will let you in on a secret, I am not submissive for your father ever and he is my little sex slave doing everything I say no matter what. Your Aunt, my older sister, is who I have submitted to since we both were in college. While she has a good cover story in her day job she actually makes her money as a dom specializing in femdom. Of course I had to tell her about our afternoon by the pool yesterday and that I wanted to start giving you lessons. She was truly so excited for us and for me. So while she told me I should switch roles with you so that we shared in the dominate and submissive roles she was also very clear that I was to begin getting you ready for her arrival tonight and for the next couple days. She wants to help you explore the fetishes that go along with femdom."

I was absolutely blown away by this and while I couldn't believe my strong father was my mothers sex toy in bed I also loved that she wanted me to be both her play thing and also for me to take charge.

She continued, "I meant what I said last night that I like it really rough and I agree with your Aunt so don't worry I will not always be the dominant one with you at first. I do like to be in full control so if you want it we can make a change, but I expect you to take charge as we explore. Thinking of me taking charge are you ready to try one kinkier thing?"

As I furiously nodded my head I got such a smile back and couldn't wait to see what she meant. Between waking up to my mother naked between my legs, the gentle ache in my balls now, the revelations of my dad just being a sub actually turned me on, and the icing on the cake my Aunt being a true dom my head was spinning. As she dove back down on my wanting cock her hand left my balls and traced between my backside and my balls. As she slowly traced her finger there and gave light pressure I couldn't believe how good it felt. Little did I know it would just keep feeling better and better as she traced her finger up to my tight sphincter and began to very lightly touch me with her fingernail slowly circling. As she continued to match the swirls of her finger with the swirls of her tongue it felt better and better.

I have to admit, I was familiar with the idea of milking, prostate massage, and even pegging. While I had seen some videos and even liked a couple JOI videos that included some anal play instructions I had never tried it. I even had a lot of CEI clips saved as favorites, but could never bring myself to do as they say after I had cum. Overall, I was always on the fence as I couldn't get past this hang up that it was wrong for guys to want that.

"Honey, I am going to milk your prostate until you cum so hard for me. It feels amazing and as I squirt this lube on my fingers I am going to start to stretch your tight back side and it will feel so good, I promise. Just relax and enjoy. Also, if you have any hang up that guys shouldn't enjoy anal get that out of your head. No it does not make you gay or bisexual to enjoy anal sex. Loving anal sex doesn't mean you love men so enjoy what you enjoy sexually and if that is prostate stimulation or full blown anal sex just ride the pleasure."

I sighed in relief as it felt so good and then as her fingers got slippery and rubbed my rose bed I actually asked her to please push her fingers inside. With a huge smile she looked me dead in the eyes and told me to beg for it. I was overwhelmed with need and immediately begin to beg her to push that finger inside me, to make me feel so good, to show me how good it could feel, and finally she slid a finger in and gently began to make a come here motion. This morning just kept getting better from the feel of her warm mouth, to the pain, to the anticipation of my aunts arrival, now to a finger in my backside rubbing against my prostate, and above all my naked mother between my legs since I woke up today. I wasn't sure how it would keep getting better and yet I knew it would.

Of course I didn't have to wait long for it to get better as she pushed a second finger inside and began thrusting the two in and out of me. She pushed in, curled her fingers, and slipped almost out, back in, curled her fingers, and out, over and over. I began making noises I had never heard myself make before and could only describe it as whimpering in pleasure as I gently rocked my backside to meet her thrusts inside of me.

"Oh my sexy stud you have such a hungry and wanting back side. It is a shame you have never played back here before as you could have been having so much pleasure as you fantasized about Amy and me in a threesome with you. Oh, I saw that in your eyes, are you thinking about Amy being here now? Her and I naked, fingering your tight hole, sucking on you, making you feel so good. I hope not, because even though I know you have thought of having a threesome with her and I remember my pleasure comes first, always. So instead you should be thinking about Amy between my legs eating me out while you grab her hair and hold her head in place all while you kiss my neck and suck on my nipples. Even kinkier, think of this my big boy. What if her legs were dangling off the edge of the bed allowing you to stand up with your hard cock fucking her so hard, but making out with me. How you ask, picture me straddling her face to hold her place, facing you, and Amy forced to lick my tight back side. Would you like see both her and my breasts bounce as you pound away, feel any one of the four of them, all while you watch me rub myself to an intense orgasm?"

I couldn't believe the mental images she was putting in my head and before I knew it she had put another finger inside me. I cried out in ecstasy and began whimpering even louder as I gyrated on her fingers. They just felt SO good!

"I thought it would take a couple of times doing this for me to get this many fingers deep inside you! It is clear your hungry, hungry, hungry back side needs more! Lets improvise then, what you didn't know is that I have had a dildo inside me this whole time and have been placing a little egg on my clit buzzing away on low. I had a little bullet vibe buzzing softly on my swollen clit and was slowly thrusting the dildo inside me as I recounted last night as you slept. Then after I quietly came watching you sleep I couldn't wait any longer for you to wake up as I knew I needed to taste you. So I've kept it in, gently rocking back and forth on it, as I played with you so you can imagine that it is now covered in my juices. You remember last night when I pushed my wet fingers into your mouth for you to taste me for the first time and then you got even harder as I made you gag on them. We are going to try something a bit bigger. Does my big boy want to taste his mommy?"

Before she even had to ask me I began to beg for her to let me suck on her toy. To shove it in my mouth with all her juices on it. To finger my wanting ass while she made me suck on it. What I didn't expect was that as she brought it to my lips it looked so realistic and really turned me on. I could smell her sex on it and as it neared my lips I opened my mouth as she stuck just the tip in.

"Lick the tip my big boy, just swirl that tongue around like you felt me do yesterday and this morning. Yes, that's it, swirl your tongue around. It tastes so good doesn't it. A pussy flavored cock all for you my big boy. Thats it, now take a little more, a little more, a little more, mmmmm, this is so hot to see! You are turning me on even more seeing this veiny, life like dildo deep in your mouth!"

Hearing that she was turned on by this I got even more into it as I moaned around it and bobbed my head up and down on it. It actually felt so good in my mouth and as it hit the back of my throat she just kept going. I gagged and then out of nowhere she slapped my balls again as I went to yell out in pain my throat opened up and down it went. I had watched so much porn where the woman deep throats a hung guy and now it was me who doing the deep throating. As with all that has happened this morning it felt incredible and I was reminded what my mother said early on, don't worry about the sexual acts, just enjoy what you enjoy and I couldn't believe it, but I enjoyed this fake cock down my throat.

"I can see you are truly enjoying this! Thats good, because when I told you last night about your Aunt really liking anal I didn't tell you the whole truth. She does like anal, but now that you know she is a femdom mistress, I will share it is giving it that she really likes. She has a few different strap ons that she pleases her clients with and she really knows how to use them as she has filled all three of my holes for years."

As she continued to slowly fuck my mouth my tongue was coated in her sweet nectar, her fingers were still deep inside of my ass, and though she hadn't been touching my cock for quite some time I felt like I was going to explode. I didn't know if that was possible without stroking it, but I felt like I was going to find out. As she pulled the dildo fully out of my mouth she leaned in and passionately kissed me.

"My big sexy son, like I said you enjoy whatever sexual desires and kinks you enjoy. So far that has included loving the taste of my nectar as you licked me to an amazing orgasm, it has included sucking on my toes, playing with my breasts, slowly making love to me as you kissed me, and it has been fucking me like your own personal rag doll as you pounded away so roughly. Now we add anal and prostate play to your list of sexual adventures and to think in less than 24 hours you've done so many taboo and kinky things! Now to go back to a little begging. Do you want your mommy to put this cock inside your tight back side? Do you want mommy to fuck you so good with it?"

As I had been, I was still completely overcome with lust and didn't let my brain get in the way of my sexual enjoyment. I wanted what I wanted and began to beg her to fuck me. As she pulled her fingers out of me she squirted lube all over the dildo making it glisten and I felt like she couldn't get it back inside of me fast enough. I felt so empty and begged her to give me that cock, to fill me up, to make me explode. Smiling she drove that dildo inside of me! My ass felt like it was on fire as the girth of this dildo stretched me even further than her three slender fingers had been doing. As I heavily breathed she grabbed my balls and yanked on them. Shifting my pain from one location to another they both quickly subsided and I felt an intense pressure against my prostate. Then the fun really started as she began to slowly give me an anal fucking and with every in and out stroke of this dildo she went faster and harder, faster and harder, faster and harder until she was truly fucking me.

"Oh my sexy son your cock is leaking so much precum! You really like mommy fucking you with her cock don't you, you really love the full feeling, the pressure on your prostate, the kinky taboo of a guy enjoying anal, the taboo of watching your mothers breasts bounce and sway as I drive this cock inside of you, and knowing you are going to erupt without anyone even touching your cock. You like that, huh, my big boy, cum for your mommy. I"ll count you down son, get ready, 5.... yes, you have been so good and waited so long this morning... 4... you let mommy play with you, to taste you, to explore even more sexually with you... 3... you like that mommy has shown you how good anal sex can be, well just wait as it is only fair that I get on all fours for you... 2... yes son, your mommy doesn't let daddy fuck her tight ass, but you are going to stick that monster cock in me and make me feel so good... 1... yes my big boy, cum just from this cock in you, thinking of Amy, you, and I never leaving this bed!"

I did what I didn't think was possible when this morning started and I erupted. Spurt after spurt of cum shot out and what was amazing is that I never shot my cum as far as I just did. I hit myself in my face, neck and under my chin! I have used this word a lot to describe this morning, but again, it was incredible. I came so hard my balls sucked in tightly to my abdomen and as I came down from my high my mother gently grabbed my balls to reposition them and then slowly squeezed and stroked the last bit of cum out, all while slowly slipping the dildo out of my back side. As I laid there both in bliss and feeling a bit empty my mother began moaning and I looked down to see her propped up by one arm, her breasts dangling down, her other arm was disappearing right between her legs, and she was sucking my cock clean, then licking up every bit of cum on my stomach, moving up to my chest, and ending at my neck and chin she licked every drop off of me. I had just come harder than I had ever cum before, including last night, and she just ate all of it! She kept moving further and further up ending with her soaking wet sex right above my face.

"Mommy is so turned on again knowing you love all the kinky things we have done and I need you to make me explode. Please eat up and enjoy, but let's keep the lessons going. Here is the lube, please coat your fingers and get one, then two, then three deep in my back side. I need you thrust them in and out of me as you taste me..."