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Carol and Sam, my new neighbors

1467 words | 11 |4.66
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I finally get new neighbors, a single mom and her teenage son.

Late last summer, I got new neighbors in the rental house next door. I watched them move in, and it seems to be just the mom and a teenage boy. In my mind, I am thinking that I can hire the kid to mow my yard, and I look forward to watching the mom, hopefully sunbathing in her back yard which I can see through my security cameras. After they get settled in that first day, I take a pot of spaghetti and a loaf of garlic bread over, and introduce myself. The mom, Carol is probably in her early to mid thirties, about 5 feet tall and nice full breasts and a nice firm looking butt. She’s wearing jean, and an AC/DC band t-shirt. Sam is a cute kid, dresses like a normal teenage boy, baggy pants, sloppy shirt, long hair. Carol thanks me and offers to share with me if I would like to stay and eat with them, but I decline, saying that they are probably tired, and need to settle in and relax a bit.

As they settle into their routine, Carol leaving for work after Sam leaves for school. I’m a bit surprised that Carol tends to wear conservative clothing, hiding that sexy body. She’s usually in jeans and a t-shirt at home.

The few times we have talked, I found out that Carol started a new job as a secretary at a local firm, and Sam is in middle school. He is also interested in computers, and he starts coming over a lot to play with and learn about computers with me. I get home earlier than Carol, so we agree Sam can stay with me until she gets home in the evening.

Occasionally I think I see a glimpse of a bra, or a peek of pink panties when Sam is pulling his baggy jeans up. Gets me wondering so I pay more attention. One day I see the waistband of his panties above his jeans, and I tug them. Sam freaks out, starts crying and tries to run out of my house. I stop him and get him to sit down on the couch and talk to me. Sam is almost hysterical, and it takes a while to calm him down and get him to talk. I sit next to him and put my arm around his shoulders, and he grabs me and hugs me tight, burying his face in my shirt.

As his crying slows to an occasional sob, I get him to look at me and tell me what’s wrong. Sam explains that the reason they moved was he was being bullied at his last school because he is so small. He told me that his mom was very supportive and changed her job and found a new town to live in to help him out. He kept skirting the issue of him wearing panties, so I asked him why he was wearing panties. That started a whole new round of sobbing.

Sam explained that he is a boy but he feels like he is a girl and he wants to be a girl. He hates being a boy. Sam explained that Carol lets him be a girl at home and he likes to sneak and wear his panties and bra when he is dressed like a boy and comes to my house. He climbs up on my lap and hugs me tight and starts crying again. I reposition myself a bit and lean back on the couch and hold Sam while he cries. I’m rubbing his back slowly, feeling the strap of the bra, and getting aroused. I run my hand up under his loose shirt and play with the strap going across his back. “Sam, can I rub the front part?”. Sam looks at me and smiles slightly and lifts the front of his shirt allowing me to put my hand on his chest. I slowly rub the thin material of what I assume is a girls cotton training bra.

Sam lays his head against my shoulder as I rub his little breasts. His sobbing quiets, and I feel him sigh, and relax. The next thing I know, he is sound asleep. I continue to hold him, rubbing his belly and breasts.

I hear the back door open and Carol walks in through the kitchen and I motion for her to be quiet. Carol sits next to me and Sam on the edge of the couch, and faces me. She sees my hand under Sam’s shirt, and smiles then I notice tears welling up in her eyes. Carol whispers “David, Sam has a crush on you! You’re all he talks about at home.” I smile and whisper for her to continue. “I see you and Sam have talked about that… well, you know, how he really is.”

“Carol, yes, Samantha and I talked. She’s going to grow up to be a beautiful woman.” I say quietly to Carol. Now it’s Carol’s turn to cry and sob and she says “No one but me has ever called her Samantha! No man has ever accepted her for who she is, and I’ve not let men get close to her because of it.” Carol gets up and leans over Sam, and hugs us both, and whispers in Samantha’s ear “Baby girl, it’s time to wake up, let’s go home and fix some supper. ” “David, can you come over tonight for supper, please? I think Samantha would like to meet you.” Samantha looks at me pleadingly, “Please come to dinner, David, for me.”

“My dear, I would be honored to come to dinner with such beautiful young ladies!” “Sam, send me an email when you’re ready for me to come over.” Samantha grabs his moms neck, and kisses her and smiles, then she grabs my neck, hugs me and kisses me firmly on the lips. Sam jumps up and runs to the kitchen as I get up from the couch. Carol hugs me again, kisses me on the lips and says “Thank you, David, thank you so much!” Carol and Samantha then walk home.

I’m so aroused that I go to the bathroom and jack off. Then I take a shower and get dressed up for dinner with my girls.

I sit at the computer to check for an email from Samantha and I’m surprised to find one from Carol. She’s never emailed me before so I wonder what’s up. I open the email and start reading:

Dear David,
Thank you! Thank you! Thank you! I cannot begin to express how grateful I am for Sam to have found such a good friend as you. Like I said, she has a big school-girl crush on you. She tells me every evening how smart you are and how she loves when you show her how to do things on the computer. She even showed me a few things, like how to send you this email!

I hope I didn’t embarrass you by kissing you earlier, it was a spur of the moment thing and I was overcome with emotion. Oh, now I am embarrassing myself. I better go fix dinner.

Sam says you better be hungry!

Thank you again!

Love,
Carol

Wow, wasn’t expecting this. Did she actually say Love? I re-read the email again, and my cock got hard again. I remembered how soft Carol’s lips felt on mine, the smell of her perfume. Damn she’s pretty hot, I just wish she would dress sexier! I don’t think I’ve ever seen her in a tight pair of jeans, or even a dress for that matter. Always slacks, blouse and sweater. She said she works in an office and it’s always cool in there. Damn, I wonder if her nipples are hard and that’s why she wears a sweater, to cover them up.

My little fantasy session is interrupted by the chime of my computer when another email comes in. This time from Sam, and it’s marked as Urgent.

Hi David, it’s Samantha.
Are you hungry? Mom said you can come over anytime you are ready. And don’t be late.
An David, don’t tell mom I told you this but I think mom likes you. She talks about you all the time. She ask me if you have a girlfriend or something and I told her you never talk about girls so she think you may be gay or something. I don’t think that though I think you like girls and I hope you like me.
Now come and eat!
Love you, Samantha

Wow! Holy shit! Both of them, yes! I am going to love seducing them both, and can’t wait to see how submissive Carol is and how I can control them both!

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11 Comments

  • Reply Indecent Perv ID:3yvnnkcd4

    In my head canon this is taking place during the early internet era otherwise no way would a woman in her 30’s need her kid to teach her how to use email lol

    • sissyboiSam2000 ID:44oefle9b0a

      thanks for your comment, but i am a bit surprised that is what you took away from the story.

  • Reply Blackbear7 ID:3zxjp5nov99

    I wouldn’t mind a alluring fling with a trans. Just might lead to something great…. Can’t wait to read part 2

  • Reply Paul ID:16loe78lyxq6

    Do you have any pictures, Samantha?

    • sissyboiSam2000 ID:44oefle9b0a

      Well, since I am a porn addict, yes, I have several thousand pics. If you’re asking if I have any personal pics, yes, I have a few

    • sissyboiSam2000 ID:44oefle9b0a

      Yes Sir, I have a few

    • [email protected] ID:1ek56s78ra

      sissyboisam2000, great stories. i love trans they are beautiful and alluring and sexy.
      email me.

  • Reply Mentallystable ID:matk1bkk6vt

    There is nothing wrong with transgender individuals. If someone feels more comfortable living life as the opposite sex then more power to them. Ill even admit I admire them for how much confidence they have.

    • sissyboiSam2000 ID:44oefle9b0a

      I agree completely, and thank you for your comment!

  • Reply Transiswrong ID:bjotki4v9c

    Transgender is just a trend made up by mentally ill

    • sissyboiSam2000 ID:44oefle9b0a

      Thank you for your comment.