Mr and Mrs Paul
Diary entries from Sam, 11 year old boy, an only child of Mary, 30 year old single mom.
Diary entries from Sam, an only child of young Mary a 30 year old single mom. Sam is a cute boy, his mom has let his hair grow quite long as a haircut isn’t in the budget. Mary recently started a new job and she and Sam had to move.
Mary was finally able to find a place closer to her new job, it was a basement apartment in a house owned by Mr and Mrs Paul. Mrs Paul works somewhere and Mr Paul is retired. The basement apartment shares the entry with the mudroom at the back of the house. Mary starts her new job in a week, but hasn’t yet found a babysitter
Wednesday
So, Mrs Paul invited me and mom for dinner. Mom put on her better work clothes, but I just have my normal hand-me-down shorts and a t-shirt that’s a bit too small. Mrs Paul is an okay cook, I think mom cooks better when she cooks. Mrs Paul keeps teasing me, says I am too pretty to be a boy! Mom jokes and says she thinks I look like a chubby little girl with my long hair! Boy I hate that!
Mom tells Mr and Mrs Paul that she hasn’t had any luck finding a babysitter yet. Mrs Paul says that Mr Paul is home all day and he could babysit Sam. I saw Mrs Paul wink at Mr Paul and he smiled. After dinner, Mrs Paul made me give her a kiss and squished me with her big boobies, and Mr Paul messed with my hair then put his hand on my butt! I didn’t know what to do, so I just stood there, then he squeezed my butt!
I got funny feeling in my belly when Mr Paul did that.
Saturday
Mom was down in the basement, and Mr Paul was on the patio reading the newspaper and I was playing in the driveway. Mrs Paul brought out a pitcher of tea and called me over for a drink. Mrs Paul and Mr Paul are sitting in the only chairs on the patio, so I stand beside the table between Mr Paul and Mrs Paul. Mrs Paul tells me again that I am too pretty to be a boy! Mr Paul laughs and rubs his hand up the back of my leg and tickles me between my legs. It kinda startles me and I spread my legs a bit. Mr Paul keeps his hand between my legs. Got that funny feeling in my belly again.
Mrs Paul said ‘Paul, isn’t she just too cute?” Mr Paul said ‘Yes, she certainly is!’
Are they talking about mom?
Sunday
I been watching TV all morning, and mom went upstairs to talk to Mr and Mrs Paul. She was gone for a couple of hours so I went to find her. Mrs Paul stopped me in the kitchen. She said mom was in the den with Mr Paul talking about rent. Mrs Paul told me I was so cute and hugged me, squishing my face into her boobies again. Mrs Paul got me a glass of milk and some cookies and sat them on the bar. Mrs Paul then sat on one if the stools, picked me up and sat me on her lap. As I was eating the cookies, Mrs Paul kept caressing my hair, rubbing my back and stuff. Made me feel good. Then Mrs Paul put her hand in my lap, and put her fingers between my legs. I got that funny feeling again and my peepee started to get stiff. Mrs Paul squeezed me between my legs, hugged me and kissed my cheek.
Mom came out of Mr Pauls den and she was wearing clothes I aint never seen her wear before. She was wearing a short skirt and it was scrunched up and I could see her panties. And I could see mommies nipples poking against her blouse.
Mrs Paul told mom to go downstairs and get cleaned up and she would go clean up Mr Paul. She then picked me up and sat me on the stool beside her, told me to be a good girl and finish my cookies, then she went to Mr Pauls den. Why does she think im a girl?
Monday
Mom is off to work so I go upstairs. Mrs Paul is getting ready to leave herself, but makes me give her a kiss and she smashes my face against her boobies again. ‘Be a good girl for Mr Paul today, okay Sam?’
‘Mrs Paul, I’m a boy!’
‘Yes baby, okay, be good!’ And shes out the door.
I look for Mr Paul, hes in his den. He’s making music on his computer so I just sit in the chair beside the desk and watch. I look around the room a bit and behind the desk is a box of magazines. I can see the cover of one and it has a pretty little girl in a very short dress. I could see her panties! I lean forward a bit to get a better look and Mr Paul says ‘Oh, I see you found my magazines. Here, you can look at it.’ And he hands me two of the magazines. The title is ‘Sissyboi Monthly’ on one and “Prettybois’ on the other.
I start to open ‘Sissyboi Monthly’ when Mr Paul says ‘Come Sam, sit on my lap and we can look at it together.’ He sits the magazines on the desk, picks me up and sits me on his lap, with my legs on the outside of his and as he sits back, he spreads his legs which makes my legs spread too. Mr Paul puts his left hand on my belly and opens the magazine with his right hand.
The index pages show lots of cute little girls in short dresses or bikini bathing suits. Mr Paul rubs his hand up my belly and I feel his fingers circle around my nipple. That funny feeling is back again. I see a couple more pages of cute little girls, then I see some man with the girl. Then the man starts undressing the girl. Mr Paul puts both hands on my hips and lifts me up a bit and moves my bottom around a bit before he sits me back on his lap.
The next page shows the little girl in her panties and bra and the man is putting his peepee in the girls mouth. Mr Paul clears his throat and coughs a little. Mr Paul aint said nothing since we started looking at the magazine. The next page the man is pulling the little girls panties down and she aint a girl, shes a boy! The next picture shows the man squirting something on the boys peepee and belly. Then the man licks and sucks the little boy, cleaning the stuff off his peepee and belly.
Mr Paul put his hand between my legs and kinda lifted me up and moved my butt around on his lap. I felt my peepee getting stiff again.
‘Do you like looking at my magazine Sam? Aren’t the little girls so pretty and cute?’
‘Mr Paul, they aint girls, those are boys!’ and Mr Paul squeezed my peepee.
‘Well Sam, they were born boys, but someone that cares for them very much want them to be girls. Very good girls!’
The next girl was wearing a short skirt and blue and white striped socks that go clear up to her panties. The next picture the man put his thing in the girls mouth like the last girl. The man pulls down her panties and pulls her butt down on his thing. Then it shows the man playing with the girls pee, wait, hes playing with the boys peepee and sticking his thing in and out of her butt, I mean his butt.
Mr Paul kinda groans and squeezes me tighter.
‘Okay Sam, time for lunch, go to the washroom and wash up and I will get started fixing some lunch’’
I wash up and go sit at the bar while Mr Paul is warming something up in the microwave. ‘Sam, I noticed that your shirt is a bit too small and your shorts are just about worn through.’
I start crying and tell Mr Paul ‘Mom don’t got money to buy me new clothes. She spent a lot to buy clothes for her new job and stuff.’
Mr Paul comes over and hugs me, ‘Oh baby, it’s okay. You know your mommy loves you no matter what you’re wearing!’ He kisses my face. ‘Did you like the clothes those girls were wearing? I have a lot of outfits like that and you could wear anything you want!’
‘But Mr Paul, those was boys in girls clothes!’
‘Yes Sam, and they were being very good girls for those that love and care about them! Would you like to be good for your mommy and Mrs Paul and me?’
‘Yes, I am good for my mommy! But im a boy!’
‘Well baby, you think about it! You can take some of those magazines with you and look at them tonight.
Monday night
Mom came in the bathroom while a was taking a bath. She said she wanted to shampoo my hair and she put some sweet smelling shampoo on my hair and washed it. She is so gentle and loving, I miss when I was little and she would sit me in the bath between her legs and bathe me. She rinses my hair and helps me out, and dries me off. ‘Sam, Mrs Paul is right, you’re much too pretty to be a boy!’
I looked at all the pictures in those magazines and got the funny feeling in my belly and my peepee got stiff again.
To be continued?
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(average: 4.50 out of 16 votes)
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Very well written, I look forward to more parts!
thank you, i appreciate hearing things like this ( and do you wish you were Mr Paul, or the boy? )
I have to admit this is a hot story. I always wanted sissyboy to mount me on all fours and fuck me but some are not interested in a woman !
too bad i dont know where you live! i like boys and girls!
A very very hot story.
When growing up I lived next door to a sissy boy. I met him when he was about two or three, already dressed like a girl. He always wanted to play as a girl and dress as a girl the entire time we were growing up. He HATED the fact that school made him dress as a boy. He only dressed as a boy in school. His mother never cut his hair until it reached his tailbone. He was a very pretty and happy girl.
did you ever invite ‘her’ over to play?
cant wait for part 2
happy to hear that!
Definitely continue this story. The idea of pulling down a little girl’s panties, only to find a small hairless penis has me harder than I’ve ever been in my life.
so glad you like it!