This is a true fantasy play story about a grown man who enjoys being treated like his Mommy's college boy.
***
I met her online. It was clear right out of the gate that we had alignment and a good connection. She needed to lead and I, as it turned out, needed to relinquish control and be directed. Her name is Vivian. I suspect that may not be her real name. She is a 40 something voluptuous woman who has a penchant for old school ways. 50's dresses, home making, and the like. Best I can tell, she doesn't have to work. She lives in a comfortable, ranch house that is very well maintained and totally updated. The large yard is perfectly maintained by her gardener.
I didn't know much about her personal life and weekends and such. We didn't talk about many things like that when we were together for our first "play dates". At that time, we rarely, if ever, break from our role playing. That fact surprised me, but it worked. We were meeting during the weekdays for our mutual escape as often as we could.
The first session went like this:
When I arrive at her house, it felt like I've just gotten home community college one afternoon. Her door is open and I come in and put my things down. She has instructed me to come right in when I arrive for our play date's, mind you.
"Hi. I'm home", I announce as I enter the front door.
I hear her in the kitchen. She comes to greet me.
"Hi, Sweetheart! How was your day?" She gives me a big hug.
She looks very nice this afternoon. She has a long 1950's dress with apron. I swear, it looks like she has stepped out of a 1950's Good Housekeeping magazine. Her hair is dark and medium length. She has a very full bosom and large, round ass. The 50's thing is her "thing". I'm ok with it. It seems to add to the scene and our play. I often wonder how and why she fixated on that era. One day, maybe she will tell me.
"Come and sit down. I just finished baking some cookies for us."
She pours me a coke at the kitchen island and she brings me a few cookies on a plate. She touches me every chance that she gets. She slides her had down my arm, she touches my hair.. When she leans on the other side of the island, her dress is unbuttoned way too much. She wants to make sure that I see her magnificent cleavage. she catches me looking and she flashes me a sweet, encouraging smile. I'm quiet, but happily enjoying this break from reality.
"Can you help Mommy with a quick chore, sweetheart? I need you to change a lightbulb for me and I don't like to get on ladders. As tall as you are, you probably can do it just standing on a chair. My tall, man."
I stand on top of a chair and unscrew the lightbulb. I hand it down to her and she hands me the new one. Once it is securely in place, I ask her to test it. She flicks it on and before I can get down, she comes over and kind of hugs my waist and says thank you. Her face presses up against my crotch. I feel a nice stirring as my cock is hardening. She does this for a long moment. Then she ends the hug by very obviously rubbing my crotch with her hand.
She feels the hardening and says, "Hmmm. Somebody's getting a little excited".
I smile shyly.
"Remember, Sweetheart. You can call me Mum or Mommy. Whichever you prefer?"
"Yes, Mommy."
She smiles again. "Yes... Mommy likes."
Once I hop down, she says, "Now, however can I thank you for your help, Sweetie? Would you like to go upstairs? I have a few ideas on what you might enjoy. Mommy will make her boy feel all happy, ok?"
I smile and shake my head. "Yes, Mommy."
She takes me by the hand and leads me up the stairs to her bedroom. Taking her total leadership is intoxicating. I don't make any decisions. She guides me to please herself and to please me.
Her room is decorated very nicely. Floral patterns and light colors. Very feminine.
"Ok, Sweetie. Would you like to help Mommy out of all of these old clothes so I can put on a robe?"
"Yes.".
"You may begin." I begin with her apron and then I unbutton the front of her dress. She sits on the long stool at the end of her bed and I remove her shoes, sweetly. When she stands up, she lets her dress fall around her ankles. She has on a lacy bra and panties that match.
She does a slow spin and lets me take in the sight of her. Gorgeous curves. Creamy skin. I can see her nipples hard underneath the lacy bra.
"You're beautiful, Mommy."
"Thank you, Sweetie. You make Mommy blush. Now you can take off my bra and panties... but no touching mommy's breasts or pussy, do you understand? We will get to that, but my big boy has to practice patience. It makes it more fun."
"Yes, mommy."
I carefully remove her bra and my eyes are feasting on her large creamy breasts and enormous nipples.
"I love your breasts, mommy. I can't wait to touch them."
"My sweet grown boy. We will get to that. I would like to breast feed my big man, would you like that?
"Oh, yes, Mommy. Very much."
"Panties, now... and no touching."
I slide her panties off from the front and I see that she is completely shaved. I also see that her pussy has creamed quite a bit and a large drop of white cream has formed on her pussy.
I venture a comment, "Wow, Mommy. Your pussy is so pretty and so wet already."
"Yes, baby. Mommy wants her college boy really badly. Can you go into mommy's closet and bring me my white spa robe."
I do as I'm told. Her closet is enormous and she has everything organized just so. It smells like lavender.
I bring her robe and she slips into it and ties it at the front.
"Ok, sweetie, Now it's your turn. I want you to undress for me. Mommy wants to to see your body."
She watches me closely as I somewhat self consciously take off my clothes. When I'm done, she tells me to stand in front of her. My cock is very hard, of course. She looks and smiles.
"Mommy loves your pretty cock." She takes it in her hand gently and strokes it.
"Now go into my bathroom and get the Vaseline our of the top left drawer and bring it to me."
I do as I'm told and when I return, she instructs me to lay across her lap.
"Are you ready for Mommy's special massage?"
"Yes, Mommy."
She lightly smacks my ass a few times. Then a few more, much firmer.
"Mommy just loves your cute little butt and I can't help but spank it. Well now, I believe I remember you sharing with me that you want to explore some of your anal desires. Is that right?"
"Yes, Mommy."
"Tell me what kind of exploration you have done so far, Sweetie. Have you touched yourself there? Put anything inside? Has anyone else done anything to this pretty ass of yours?"
It was surreal... Seeing as I was laying there across her lap with her hand caressing my ass, and I was about to answer intimate questions about my anal desires.
"I have put some small things in there before while masturbating. It feels good. Nothing else."
"Very good, then. I think we will have to explore a little more here and see how we both like that. I enjoy some anal stimulation, too. If you are a really good, I might just let you help me with that some time. Now, on to Mommy's special massage. Now I am going to put some vaseline on your butt hole and massage you a bit. After we do that, I want to give you an enema. I want my man clean. Inside and out. Are you ready?"
"Ok, Mommy. I'm ready."
"Now Mommy is going to spread those ass cheeks a bit. Here we go."
She uses both hands. One on each cheek. She squeezes and then separates my ass cheeks.
"There's my little red butthole. Mommy has been looking forward to doing this for her man."
She took a large dollop of vaseline and began to massage my asshole. I moaned a happy sound, because it felt so good. She had me lift my ass in the air a bit and she put a pillow under my front. She also took the opportunity to squeeze my cock and comment about how hard I was.
My ass was up in the air and this woman was massaging and spreading my ass cheeks. I felt embarrassed, ashamed, and incredibly turned on that I was allowing this.
"Ok. Time for my fingers to go inside, Sweetie. Take a deep breath."
She didn't start with one finger. She went in with two. God it felt so good.
"Oh, Yes Mommy."
"I'm glad you like it."
She increased her pace and the movement of her fingers when they were inside of my ass. She was quite literally finger fucking my asshole.
"I'm going to put one more finger in, OK? You can take that for Mommy, can't you?"
"Yes, Mommy, I can take it."
She put the third finger in and my asshole felt so full. I thought I was going to cum but I didn't. I am sure that she would have been greatly disappointed had I cum at that early moment.
She slowed her pace and removed her fingers from my somewhat stretched asshole.