After the first time I had success with finding a woman to watch me jerk off on Craigslist I decided to try again. There was not a lot of immediate success again. A few months later I did have someone respond though. A woman who described herself as a tiny strawberry blonde who wants to more than watch. Well that sounded fun. We emailed back and forth a few times and I sent her my picture. She sent hers back – short and curvy with big breasts, slightly longer than shoulder length strawberry blonde hair. She invited me to come over to her place that evening and jerk off for her.
When I reach her house she greets me at the door wearing a short, revealing sundress with her large breasts almost falling out of the top of it. She invites me in and asks if I’d like to relax and have a drink with her. That sounds good to me and we head inside and I have a seat at her kitchen counter while she gets each of us a beer. We talk about some mundane shit for a few minutes and she asks if I’ve ever done something like this before. I decided to just blatantly lie and say this is my first time, but that having a stranger watch me jerk off has been a fantasy of mine for a long time.
As she is talking she’s leaning against the counter towards me, and her dress is starting to show a bit more of her breasts. I can see the hints of freckles on the tops of her breasts where it would usually be covered by her bikini top. And the little bit of her apparently quite large areolas sticking up above the top of the dress. I’ve honestly been somewhat hard since I arrived at her place, but seeing more of her breasts has gotten me really hard and I can feel the wet precum starting to stick to my jeans. I start rubbing my hard cock back and forth through my jeans. I don’t think she can see that from where she is, but that *is* why I’m in her apartment.
“So why has this been a fantasy of yours for so long?” she asks me.
“It’s hot having someone watch you jerk off. Don’t you agree?” I ask her. “Plus there’s the hope that they’ll be so turned on that they’ll start something more. Maybe she’d start touching herself. Or want to join in.” At this point I’m rubbing my cock pretty hard through my pants. I’m wondering if I should just take it out and show her. I don’t think it’s too forward of me, and I quickly undo the button on my jeans.
“Is that what you’re hoping will happen tonight?” is her next question as she leans in a bit more. I want to just reach over and pull the front of her dress down and free her breasts. Instead I stand up, then quickly pull my jeans and underwear down to my ankles. I stand there in front of her and stroke my cock slowly now that it’s free. She looks down at my cock and then takes a sip of her beer. It’s a bit of a cliche, but as the beer bottle touches her lips I imagine it being my cock instead.
“Yeah, that’s what I’m hoping for,” I say. “And you did mention that you want to more than watch. What do you think?”
“It’s a nice cock,” she says, “but I wasn’t expecting to see it so soon!”
“Well, this is the reason I came over here,” I respond, “and I was noticing your breasts when we were talking. It was making me hard, so I figured I might as well… I can put it away if you want though.”
“No, don’t do that,” she says smiling. She walks out from the kitchen and crosses into the living room, sitting down on the couch. “Come over here so I can get a better view though.”
I pull my pants and underwear off completely, followed by my socks, then take off my shirt and leave it on the pile by the floor there. I then cross over to her in the living room and stand across the room from her. I do think briefly that I should’ve brought my pants across the room because the condoms are in my pocket, but that’s not a huge issue if I end up needing them. I slowly stroke my cock with my left hand, getting it nice and slick with precum now, while my right gently fondles my balls. “So what do you think,” I ask.
“Hot,” she replies succinctly. She puts her feet up on the coffee table and spreads her legs a bit in doing so. Her dress rode up a bit when she sat down, and I’ve got a nice view of her thighs. I’m not quite able to see what type of underwear she’s got on, but it’s close. She pushes the dress down between her thighs with her right hand and then rubs her inner thigh up to her pussy. “So how do you imagine this working? Do you want to watch me rub my cunt while you jerk off?”
“Whatever you want to do, but I’d very much like to see that,” is my response.
She spreads her legs a bit wider and pulls her dress up with her hand. Apparently the answer to what type of panties she’s wearing is none, and everything is shaved smooth. It is hot watching her start to rub her pussy for me, spreading her lips with one hand and rubbing herself with the other. All while her eyes are still focused on me and my cock.
We watch each other masturbating for a little bit, and I enjoy watching her get more and more turned on. Seeing how her skin starts to get a little flushed, and how her sighs get slightly louder. Watching how wet her pussy is getting. I start walking around the coffee table towards her. “Your pussy looks so fucking wet,” I tell her.
“I’m so fucking wet,” she says, “thinking of riding your big, hard cock. Feeling you cum in my pussy. You want to cum in me?”
At this point I’m right in front of her, jerking my cock off right in front of her face. I take my hand off my cock and grab a bunch of her hair and push her face down to my cock, pushing it into her mouth. She looks up at me as my cock is in her mouth, and I guide her head back and forth. My other hand reaches down and pushes the straps of her dress off her shoulders then pulls the front down a bit to finally expose her breasts. They’re huge with light freckling on top and equally huge light pink areolas. I let go of her hair and she lets my cock out of her mouth, taking a deep audible breath as she does. She kisses the side of my cock as her hands come up from her pussy to stroke it a bit, and play with my balls. “Mmm, I love the taste of your cock on my lips,” she tells me.
I pull her to her feet then kiss her as I push her dress down all the way to her feet. My hand is between her legs fingering her, and I can feel how wet her inner thighs are. How dripping wet her pussy is at this point. I grab her thick ass and then push her back down onto the couch and kneel down in front of her. She moans loudly and I feel her hands on the top of my head as I start licking her. Her thighs grip the side of my head momentarily before she pushes me away, “Fuck, I need your cock in me when I cum.” She leans over to the end table and grabs a condom from it.
I sit up on the couch next to her and start stroking my cock again. She kneels down on the floor in front of me and licks my cock and balls while opening the condom. I’m watching as she unrolls it onto my cock and then stands up, turns around and sits down on my lap. She adjusts herself a bit and then guides my cock into her pussy. “Mmm, your pussy feels so tight on my cock,” I moan in her ear. I lean against her and bite her shoulder gently while taking her big breasts in my hands. She’s leaning forward now and bouncing on my cock.
As she fucks me harder I grab her hair with my hand and pull her head back to mine. “Is this what you wanted when you started seeing me jerk off? Feeling my big cock deep in your slutty pussy? Ending the night filled with a stranger’s cum?” I ask as I can feel the spasms of her pussy around my cock.
She pushes back against me a bit. “That’s what I want. I want to be your little slut. Have your cum all inside me and over me.” She grinds her ass against me and then screams loudly as she cums, and I wonder if the neighboring units are getting off listening to her. She writhes on my cock a bit and turns around to kiss me. “Where do you want your cum?”
I kiss her neck and run my hands along her body, from her smoothly shaved pussy up to her big breasts. “I want to tit fuck you and cum on your face,” I whisper in her ear. She smiles a bit and climbs off of me, lying down on the couch. She reaches up and pulls the condom off of me and starts to stroke my cock. I straddle her chest as she takes my cock and rubs it between her big breasts. I thrust a bit with my hips and quickly feel myself about to cum. I grab my cock in my hand and stroke it and enjoy watching the semen shoot out onto her mouth, chin, and cheeks while she plays with my balls.
I collapse back onto the couch next to her. She grabs some tissues from the coffee table and wipes the cum off of her face. “Is this how you thought this would go?” she asks me finally.
“Pretty much what I was hoping for,” I reply. We lie there quietly for a bit before starting to talk. During the conversation she starts stroking my cock and we end up fucking again before I go for the night.
Source: reddit.com/r/sexystories/comments/md4ptd/going_over_to_her_apartment_to_jerk_off_for_her
I love when a woman watches me jerk off — and it is even better when it makes them want to participate. Great story.