I wrote this as a reply to someone’s request on /r/dirtypenpals. She didn’t reply and deleted her post, but I had fun writing about it and feel it’d be a shame not to share it…
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It’s a quiet Friday night; your previous plans for the evening fell through. You’re sitting alone in your room and you can hear the muffled sound of your parents’ TV coming from downstairs. Your phone buzzes – it’s a text from me.
It’s not the first time I’ve texted you, but usually it’s to get in contact with my son when he’s with you (he never checks his phone). But tonight your BF is in another state, so why am I messaging you now?
We chat for a bit, and it turns out we’re both bored this week with my family’s absence. I ask you about my son, checking in to make sure my son is being a gentleman.
“I hope he’s not being too pushy with you,” I text. “Boys his age can be… demanding.”
No, you say, he’s not like that at all.
“Well now it sounds like you’re complaining!” I joke back. You’re alone in your room looking at your phone, but you blush.
“I’ve known you both for years, I can help you out if you’d like. Swing by any time and we can have a talk.”
*Okay*, you say.
There’s a knock at your door? You were so engrossed in our chat you’re surprised and your immediate reaction is to assume that it’s me knocking.
Your father walks in, asks what you’re doing. *Just texting a friend* you say. You can’t quite put your finger on it, but for some reason you don’t want to tell him you’re talking to me.
Your father says he just got off the phone with **me**. Apparently I forgot my phone cable at the office and need to borrow one from them. (Strange, I didn’t mention anything about a phone cable to you…) Your father hands the cable and his car keys to you and asks you to bring it over to me.
Fifteen minutes later you’re ringing my doorbell. I seem surprised when I open the door. “Thanks, but I wasn’t expecting you to deliver it.” You notice a bit of a grin on me. “Come in, come in.”
You step in, hand me the cable which I toss onto the dining room table. I’m a foot taller than you, even in my bare feet. I’m wearing relaxed Friday night clothing: plaid pajama pants and a sweater. I lean up against the table and fold my arms.
“Since you’re here, there’s something I would like to talk to you about. I care about my son, I want what’s best for him. I think you two are a great pair, he’s a lucky guy.”
You smile and thank me.
“I have to ask this… are you two *active*?”
*Active?* You’re confused.
I sigh. “Sexually active.”
*Oh, not really.*
“Not really? Look, I know it’s none of my business but I want to make sure you two are being safe and that things are done properly, that’s all. It’s for your own security.” I stand up and gently place a hand on your shoulder.
You assure me that there was sex-ed at school, and that you know the basics about protection and all that. To your surprise, I laugh.
“Well, that’s half of it I suppose.”
*Half?*
“You know how to not get in trouble but, let’s be honest, it’s supposed to be about pleasure. About having fun! That’s the stuff they don’t cover in school.”
You laugh too. This is the first time we’ve had a talk like this, and it’s going well. You’ve known me for years and we’ve always gotten along well. You’ve always seen me as a future version of my son, a preview of what he’ll be one day.
“You said you two aren’t really sexually active. I bet you’re scared, you’re hesitant to try out new things quickly. Don’t want to mess up the first time, right? That can be disastrous for a relationship!”
*Disastrous? Really?*
“Oh god yeah. Trust me, you can date someone for AGES but you won’t really know if you’re compatible until you really get intimate. That’s an important part of any relationship. So you don’t want to rush into it and mess it up on your first try.”
You frown, thinking hard. You tell me that I’m only making you more nervous now! We laugh again.
I start rubbing your arm. “Look, I want to help you. I can teach you those things you’re missing. We’ll keep it between us.”
You smile and feel your face go red.
“You’re blushing,” I tease. “I can take that as a yes?”
You laugh and smile.
“Ok, you need to be home soon so we’ll just cover one thing tonight before you go.”
*What’s that?*
We’re alone in my house, but I lean in close and whisper into your hear. “Have you ever given a handjob before?” You shake your head ‘no’.
I still have a hand gently holding your right arm. I slowly slide it down and take your hand. My hands are large, firm and warm. Yours are small and trembling slightly.
“It’s okay,” I assure you. We look down and you see me take my other hand and I pull my plaid pajama pants out and down, revealing my swollen cock.
Your eyes widen, your jaw drops. This is the first cock you’ve ever seen. Your heart is pounding.
With my other arm I take your right hand and gently place it on my cock. It’s warm to the touch. Gently I guide your fingers around it, and show you how to gently stroke the shaft. We’re speaking in whispers, but my voice is getting deeper and more tense. You don’t say a word and your eyes remain fixed on my bulging member.
“A little harder,” I say. You tighten your grip. We lean in closer to each other, you hear my heavy breathing in your ear. “That’s it… you’re doing good…”
We’re standing in my dining room with my pants around my knees. My throbbing cock is in your hands, growing harder with every stroke. I now move my hands, saying “Keep going,” as I move them up and start holding you by the hair.
You feel my wedding ring against your cheek.
“Look at me,” I command. “Don’t stop.”
You stare up into my eyes. For a brief second you realize where you are and what you’re doing: *you’re in your boyfriend’s house, giving his dad a handjob*. A wave of shame washes over you, followed immediately by a warm wave of passion through your whole body. You now notice how wet you’ve become, and I’ve barely touched you at all.
You whimper.
I’m holding you by the head and hair when I lean in and start kissing you. Somehow *this* seems a bit too much and you try to pull away, but I’m holding your head in place. You’re about to protest when I yank your hair back and you let out a yelp.
“You’re doing well,” I say. You notice that you never stopped stroking my cock, and now it’s starting to flex and pulse. “I’m going to cum.”
I push you down to your knees before me. In a stern voice I say “On your face or in your mouth, it’s up to you.”
Without saying a word you open your mouth. I place my hand over yours on my cock and we start jerking harder. In a few short seconds I start grunting louder, moaning. I throw my head back, then push my cock deep into your mouth.
I let out a loud groan that can be heard throughout the house. My cock twitches and pulses and suddenly you feel my cum spraying into the back of your throat, warm and sticky.
It’s too much. You pull back and start coughing and gagging. You lean forward, coughing my mess onto the floor.
By the time you wipe your eyes and look back up, I’ve pulled my pants back up and am staring down at you.
“That was good. You made a mess at the end there, but you’ll get the hang of that.”
I walk out of the room and return momentarily with a face cloth for you. You clean yourself up without saying a word.
“That was a good start,” I say. “But I guess I owe you one too. Why don’t you come by tomorrow?”
You nod. I guide you to the door and we exchange polite goodbyes like nothing happened.
Source: reddit.com/r/sexystories/comments/5d0zzr/your_boyfriends_father_str8_mf_reluc_mdom
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nice story
Not a fan of the second person, but otherwise great read. Didn’t over assume the readers emotion, etc. good job.