I Let Her Watch Me Stroke to Her Photos — BDSM Stories

I heard the door click shut behind me as I stepped out onto the quiet street. It was just past midnight on a Friday, the air cool against my skin. My mind stayed stuck back in that apartment, replaying every curve and every command. I somehow found my car in the dark lot even though my thoughts were miles away. On the drive home I kept turning over the past two weeks. Sadness hit me hard because I knew I would never see Sarah again, yet a quiet relief settled in my chest too. My divorce had been final for three months, closing out four long years of marriage. A few weeks back I had posted a profile on a busy dating site. I wanted to meet someone fresh even though doubts kept nagging me about rushing into anything serious so soon.

My time with Sarah began ten days earlier and wrapped up an hour and a half ago. Those ten days crackled with excitement unlike anything I had known with women before. I drifted back to that first night, Wednesday evening the week prior.

Unexpected Message

Ping. A new message always sent a quick rush of hope through me. I had not received a single reply to any messages I sent in three days. Maybe one had finally landed. I opened my inbox right away. It was not a reply to one of my intro messages. It came from a profile called Lauren286. A woman writing first was rare. Even more surprising, it was not to my main profile. It landed on the private one instead.

The site let you keep a second profile for more private kinds of meetings. I had written that profile around fantasies my ex-wife never knew about. It focused on what some people call gentle femdom, heavy on body worship, especially breasts and pussy. Lauren286 had answered that profile directly.

I wrote back right away and we moved into chatting. She told me to call her Sarah. I figured that might not be her real name, so when she asked for mine I glanced at the TV. An episode of The Simpsons was on, so I said my name was Bartholomew but she could call me Bart. I felt dumb the second I typed it, but I was stuck with it now.

We traded photos next. I sent a simple head-and-shoulders shot. She said she liked it and did not ask for more. She seemed eager to send hers instead, and she sent several. “I sent you the first one, Bart,” she wrote. “Tell me what you think, and be detailed. I like hearing how much someone likes the way I look. Throw in any dirty thoughts that come up. I will be disappointed if you do not have any.”

The first photo showed her lying back on a sofa. She had shoulder-length blonde hair, her legs crossed and stretched toward the camera. She wore sheer black stockings, a short skirt, and a tight sweater with horizontal stripes that curved over her large breasts. No shoes, so the stockings showed her feet clearly down to the toes. She looked straight at the camera with a teasing smile that made my pulse jump.

“Beautiful, pretty girl, lovely hair,” I typed.

“Yes, yes, I know I am beautiful, Bart, but you can do better. What are you really noticing? What naughty thoughts are you having? Is the photo making you want to touch me?”

I decided to be completely honest. “Big boobs, D-cup, love the sweater. Nothing shows off nice tits like stretchy fabric with horizontal stripes. No cleavage showing, but that just makes it hotter. Probably braless.”

“Wow, Bart, that is really good. I agree with all of it and I am glad you said so. Except the D-cup part. They are double-D. An experienced eye would have caught that, but do not worry, it will be obvious in the next photo. Do not stop. You are doing fine. Keep going.”

“Okay,” I wrote. “I love your legs and the way you have them crossed and pointed at me. I love all kinds of black hosiery, especially sheer like that. I also like that you are not wearing shoes.”

“Well done again. My legs are fantastic in sheer black stockings. Are they giving you any sexy ideas? I hope so, Bart.”

“Yes. I really want to touch them, feel the soft material, run my hand all the way down to your toes and then slowly back up and under your skirt until I find out whether you are wearing stockings or pantyhose.”

“Ooooh. That is a great idea. If I were a guy I would want to do that to me too. Maybe you will get the chance.”

“Well, Bart,” she continued, “I am sure you could stare at this photo for another hour, but it is time for the second one. Before I send it, though, I think you would enjoy it more if you took off all your clothes. I know we cannot see each other, but you will be more comfortable looking at this next one while you are naked.”

I agreed and told her when I was ready.

“Great. Now that you are naked I will send the second photo. Unless you want to look at the first one again for a while. I would understand.”

I knew what she meant and almost said yes, but I told her I wanted to see the next one. She sent it. It was a waist-up shot of her in the same striped sweater, lifting it with both hands and showing her breasts. She stared straight at the camera with a wicked grin that seemed to say look all you want but do not touch.

I knew what she expected by now. “Oh my God, Sarah, they are amazing. Huge, natural, heavy, but still holding a nice shape. Slightly pointy with beautiful hard nipples. Did I miss anything?”

“They are all that and more, Bart, and I know you must want to touch them. The real question is whether they are causing any changes down there. Are you getting hard? Are you touching yourself? It would be completely normal if you were.”

I was fully on board now. “Yes, Sarah. I felt it the second I saw the photo. I am completely hard. I am stroking myself while I imagine kissing your tits.”

“Ah, I expected nothing less. Go slowly, Bart. That photo could finish you off, but there is still one more you will not want to miss. It could make a mess very fast, so be ready.”

“Please send the third one now before it is too late. The first two are open side by side on my screen. A 34-inch screen, Sarah. I cannot last much longer.”

“Okay, it is sent. It will answer your question about what is under the skirt. Try to give me some good feedback before this one finishes the job.”

In the third photo she had uncrossed her legs and spread them wide. Her breasts were still out, but she was leaning back so only the undersides showed and the nipples pointed straight up. It was an up-skirt view. She wore stay-up stockings with a pattern at the top and tiny white panties. I could see curly blonde hair around the edges.

“Oh God, Sarah, I want to rest my arms on your legs and kiss your thighs right between the stockings and your panties. Then I would kiss you lightly on top of the panties and feel that curly hair on my lips and…”

“Yes, Bart, and then what?”

“Sorry, Sarah. The third photo just made a mess here. I hope you understand.”

“Do not worry, Bart. I totally understand. I am surprised you made it past the second one. Some guys did not. I tried to tone the third one down by keeping the panties on, but I know it is still strong. You had too much at once: the up-skirt view, my curly blonde hair showing around the panties, sheer nylon stockings, bare thigh, the underside of my breasts, my face looking right at you, and that smile. You never had a chance. It was unfair and completely my fault. Sorry about the mess.”

“Whoa, easy, Sarah. You are going to make me want to run to the bedroom with that photo. Warn me next time.”

“Okay, Bart. I have to go now. You should come see me Friday evening. You will be in paradise. I will wear the same outfit, with the same body underneath, lol. But it will be much more intense than the photos, so be ready.”

“Yes, I would love to come. Thank you, Sarah.”

“Okay. I will send the address Friday morning. Eight o’clock. I am not free to chat tomorrow night, but you have three photos to enjoy. Get naked first, start slowly with the first one, and spend plenty of time with it before you move on. You can tell me all about it Friday. I will want every detail. Goodnight, Bart.”

I started to reply but she was already gone. I tried to think how I would describe her personality. Words like vain or self-absorbed came to mind, but whatever it was, she turned me on completely. I had started out just playing along, but at some point it stopped being an act. The excitement became real, and I could not say exactly when that shift happened. Either way, I could not wait for Friday. I knew I would follow her advice on Thursday night and start with the first photo. She might ask me about it.

Friday Evening

Sarah met me at the door wearing exactly what she had worn in the photos. My face must have shown how much I liked it, because she said, “You love it, do you not, Bart? My outfit, I mean.”

“Yes. You look very beautiful, Sarah,” I answered honestly.

“I know that, but do you find me sexually arousing dressed like this?” she asked with a small grin. “That is what matters.”

I took another look at the tight striped sweater stretched over her double-D breasts, the short black skirt, the sheer black stockings, and her bare feet. “Highly and most definitely,” I said.

“Good answer. Come in. Make yourself comfortable. You can leave your clothes on that shelf by the door.”

I hung my jacket and turned toward the kitchen.

“All your clothes, silly,” she said.

I looked at her to see if she was serious.

“Yup. Everything. Shirt, pants, underwear, socks,” she added, smiling.

I started undressing. Sarah stayed dressed. “Are you not joining me?” I asked.

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“Clearly I do not need to,” she said, sounding pleased with herself. “You already told me you find me highly sexually arousing exactly as I am. I want to see if that is true.”

I had said it, so I finished taking everything off and put it on the shelf. At least I had already seen her topless in the photos.

“Perfect,” she said. She took my hand and led me to the sofa. “Have a seat while I make drinks. Rum and coke okay?”

“Yes, thank you.” I did not care what it was as long as it was strong.

She turned to go, then spun back and bent down to look closely at my cock. “Is something wrong, Bart? I am not seeing any sign of the reaction you promised. Do I need to jiggle my tits or something?”

My penis was at its smallest, between two and three inches and pointing almost straight out because my balls were large and tight underneath. Before I could answer she said, “Perhaps a small spark is needed to get things started.” She pulled me into a quick hug, kissed me on the mouth, pressed her leg between mine, and mashed her breasts against my chest. One of them shifted and confirmed she was not wearing a bra. Then she let go and walked to the kitchen.

I stood there replaying the three seconds of contact while she poured the drinks. She came back less than a minute later.

“Ah, now we have the reaction,” she said. “The fire is lit. I was starting to worry.”

I looked down. I was fully hard, pointing up at about sixty degrees, a little under five inches and fairly slim. She handed me my drink, had me sit, and sat right beside me so her fully clothed body pressed against my bare skin. My cock pointed straight at the ceiling.

“Cheers,” she said, touching her glass to mine. I took a big swallow.

I decided it was time to run my hand up her leg the way I had imagined. I placed my left hand on her thigh and started to slide it upward under her skirt. She stopped me.

“No, Bart. Not yet. There is something I would like you to do for me first.”

She handed me a tablet. “Bart, two nights ago you told me how aroused you got looking at my photos and how you masturbated to them the last two nights. That pleased me a lot. Now I want you to show me exactly how you did that while I sit here next to you. The three photos are on the tablet. You can swipe between them. It would feel as good for me as for you. Will you do that?”

“Sure,” I said after a moment.

“I will start with the first one, like I did last night.”

“Perfect. The first one is very arousing. I posed for it myself,” she added with a small laugh.

I was already hard, so I picked up the tablet, brought up the first photo, and began to stroke myself slowly.

“Speak your thoughts out loud, Bart. I want to feel part of it.”

“Okay. Feel free to lend a hand if you like.”

“Oh, that would be cheating. It would be over too fast. Maybe later if you ask nicely.”

“I really want to see that woman topless,” I said, looking at the photo. “They must be huge. The way the sweater stretches over them already excites me.”

Sarah sighed and leaned closer so her right breast pressed lightly against my left arm. I swiped to the second photo.

“Wow. The woman heard me. They are even more incredible than I imagined.” I stroked faster. “I have never seen such beautiful tits, but she knows it from the look on her face. I really want to reach out and touch them.”

Sarah sighed again and pressed her leg against mine. I took the hint and swiped back to the first photo.

“Please, woman, reach out with that beautiful leg and touch my balls with your stockinged foot. Yes, like that. Do not stop.”

I swiped to the third photo. “Spread your legs wide for me. Give me that up-skirt view. I love how your tits point up. I am so close now. Please push your panties aside and show me your pussy. Yes, beautiful. I really want to kiss it.”

I came hard, straight up and back down onto my balls. Sarah let out a sharp sound of pleasure.

“That was incredible, Bart. Was it that good the last two nights, or did having me here make it better? I am sure it did. I enjoyed that every bit as much as you did. It made me feel so desired.”

She turned suddenly, wrapped her arms around me, and kissed me hard, pressing her breasts to my chest. “Come with me, Bart. I will clean you up.”

She led me to the bathroom, wet a washcloth with warm water, and gently washed my balls and cock. Even though I was spent, it felt good and I did not want her to stop. After she dried me she opened a drawer, took out a thin white ribbon, and wrapped it around my balls, tying it above my cock like a cock ring.

“It is almost not long enough for you, Bart. You could use a cup from one of my old bras to hold these things. Ah, my lovely bras. I look amazing modeling them. Remind me to send you a picture of me in a nice bra. You will not be able to get your clothes off fast enough, believe me.”