How I learned I love being watched while fucking [MF]

I (46M) have been reading all of your incredibly sexy stories here for a long time but I’ve never contributed any of my own. I’ve wanted to write about this completely true experience for a while now and am finally sitting down to do it. It takes place a long time ago, long enough to make me feel like an old man, and it ranks high on the hottest five experiences of my life (most of which, now that I think about it, involve sex in front of other people). I’m not into swinging. In fact, if I’m honest, I have a jealous streak that probably borders mildly on physical possessiveness. Instead, my kink is more in line with “showing off” the ladies I’ve been fortunate enough to share time with and make love to. Anyway, onto the story. It’s going to be a bit long….

Ashley and I were both 18 at the time. We were high school sweethearts and had dated since the beginning of our sophomore year. Ashley was way out of my league (reflecting, I’ve somehow managed to date, and marry, out of my league most of my life). I’m no scrub, I know I’m a decent looking guy, but if Ashley was a 9, I’d be happy to be called a 6.5. She was half Korean, 5’ 5” and 110 lbs. She ran cross country and had a long, lean runners body with incredible B-cup breasts and perfect, small light brown nipples that were framed spectacularly by her boob-length, Jennifer Aniston-cut dark hair (this was the mid-90s after all - chicks loved Rachel’s hair in Friends). And that ass…oh my god, that ass.

I, on the other hand, could only be described as fucking skinny. At 5’ 9” at the time, I weighed 130 pounds, but I was as “shredded” as a lanky guy like me could be due to wrestling all four years of high school. I had short brown hair and was about as pale as they come thanks to my Scottish heritage, especially so when juxtaposed against Ashley’s golden bronze skin.

We were walking down the street one exceptionally warm day and popped into a Dairy Queen for a Blizzard. As we left the restaurant, a car pulled up to the curb, the window rolling down as it stopped. The man inside asked if we knew where the closest grocery store was, and I told him it was about 2 miles up the road.

“Thanks,” he said. “Hey, my name’s Bill. Do you mind if I ask you one more question? Are you two dating?”

“Yes….”

“I’m a professional photographer and I like to shoot couples and have a lot of connections in the advertising business. Would you guys be interested in a photo shoot? I’d be happy to compensate you for your time. You both have really distinct looks and, who knows? It might lead to some modeling gigs. You’re both at least 18, right? I want you make sure we don’t need parental consent forms.”

Ashley and I looked at each other and both shrugged. “Sure, I guess. I’m Jake, this is Ashley. And, yeah, we’re both 18.”

“Great! I have a studio in (a town 45 mins away) with wardrobe and everything. We’d shoot for an hour and then I can bring you back here. Would you guys be comfortable doing some swim suit shots too?”

“Ummm, yeah, but I don’t have a suit with me,” Ashley responded.

“Well, if this goes well, maybe we save that for next time,” Bill replied. “Ashley, one other thing, would you be open to doing some more risqué looks? Like, maybe topless?”

“Uh, no, not my thing.” Ashley turned to start walking away.

“Wait! Sorry, maybe that was a little too forward. Listen, if you’d like to reconsider, I can pay you $150 each.”

Ashley looked at me with an expression that said “maybe?”

“One more question. Are you two, um, sexually active?”

I said yes at the same time Ashley turned to walk away again. She bored into me with a look that screamed “how dare you tell him that?”

“If you two would be willing to let me photograph you having sex, I could pay you $300 each. The photos will never be published. Nobody will ever seen them except me. They’d be for my own personal (ahem) purposes.”

Now, a brief aside to explain. $300 each isn’t an enormous amount of money, but this was 1996 and gas could still be had for 99 cents/gallon if you knew where to look. Further, I’d grown up solidly upper-middle class, but after my parents divorced when I was 12, my dad effectively “retired,” content to squeak by on his savings for the rest of his life, and while my mom was still a working professional, she spent money like it was burning a hole in her pocket. While she always made rent, we were constantly getting collections calls at home, probably due in part to the 3 new cars she’d bought in the last 5 years. I’d worked at KFC earning $4.25 an hour for the last year and an half and mostly had to take care of myself aside from shelter and food.

Ashley had it a lot harder. Her dad was an alcoholic and had mental health issues that, while he was a genuinely nice guy, left him working odd jobs here and there. Her mom worked a minimum wage job at the YMCA and collected welfare. Ashley was the oldest of 3 kids and her parents constantly struggled just to keep them In decent clothes and shoes. $300 each wasn’t life changing for either of us but it was a huge amount of money to us both at the time. Ashley had all but given up hope of traveling with her cross country team to the state championships, but $300 made funding a nonissue. For me, it was enough to replace the alternator in the 1972 beater that had been sitting in my driveway for the last month and maybe even get a stereo installed (every 18 year old’s top priority at the time).

Ashley grabbed my arm to pull me away but I reminded I reminded her of the championships.

“Babe, are you seriously considering this? It’s gross, he’s gross, this is just disgusting,” she exclaimed.

“Ash, we could both really use that money. I’m not going to pressure you at all and I really don’t want you doing something you’re not comfortable with, but I think I’d be in.”

Ashley thought in silence for probably 10 seconds that felt like 15 minutes. She pulled my arm down and whispered in my ear “if I think about it, this is actually kind of turning me on but do you think this is safe?”

I looked back at Bill. He looked exactly what you would think a guy driving around in a beige 90s Toyota Tercel trying to talk 18-year-olds into getting naked would look like. Greasy hair, probably 150 lbs, beer gut, bad teeth, yellow-tinted sunglasses, an ashtray full of cigarette butts. I was confident that unless he was armed, I could take him. I looked at Ash and nodded. In retrospect, this was the dumbest thing I’ve ever done, especially with Ashley with me, but I was seeing dollar signs flash before my eyes. Be smarter than I was y’all.

“We don’t have 2 1/2 hours for this,” Ashley said to me.

“Instead of the studio, there’s a hotel I know up the road we can shoot in,” Bill interjected quickly. So much for his ruse of needing directions to the grocery store…. “I can drop you both off at home in an hour and a half.”

Ashley thought for a few more seconds then broke a sly half smile. “Ok, let’s do it.”

We got in the back of Bill’s car and he drove 5 minutes to a motel that looked like it rented rooms by the hour. It probably did…. We waited in the car while he checked in in the lobby and then walked into the room. It was small, barely large enough for the queen sized bed, and it stunk off stale cigarettes. But it was clean. “Let’s set the mood” Bill said and put a 70s porno on the TV. “Whenever you guys are ready” he said while taking his camera out of a leather satchel.

I looked at Ashley and then started unbuttoning my shirt. “I can’t just get naked right here,” she said. “Let me freshen up in the bathroom for a minute.” I stripped down to my boxers and sat on the edge of the bed while Bill tried to make small talk and stared at the porn on the TV.

3 or 4 minutes later, Ashley emerged from the bathroom wrapped in a towel. “You guys just do what you would normally do. Pretend I’m not here,” Bill said. It was a short-lived suggestion as he almost immediately began directing the “scene.” Figuring I should be bolder one of us, I dropped my boxers and stepped toward Ashley. My cock was already at full attention from excitement and I was relieved the nervousness I felt wouldn’t keep me from performing.

I kissed Ashley and lowered her onto the bed, towel still wrapped tightly around her svelte, firm body. My heart was pounding out of my chest. We’d lost our virginities to each other and enjoyed sex whenever two 18-year-olds who both lived at home could find the opportunity, but this felt different. The butterflies, the thought of this stranger seeing my gorgeous girlfriend in her rawest, most primal state, the feeling was almost overwhelming.

We continued to kiss. I looked down at Ashley and could sense her apprehension but also something else. I could feel her heart beating as hard as my own, but she smiled and looked up at me with her gorgeous, almond-shaped deep brown eyes with a look that betrayed her own excitement. It was then that I heard the first click of the camera shutter, followed by the slow electronic hum of the camera advancing the film (pre-digital cameras, mind blowing, I’m sure). Slowly I loosened the tuck at the top of the towel and peeled it back. Unsure of how she would react, I instinctually covered her left breast with my hand and immediately felt her nipple harden into my palm. Her right breast was still loosely covered by the towel.

I mentioned Ashley’s perfect light brown nipples before. What I didn’t mention was how amazingly long they were. Not “WTF?” long, more like “wow, those are special” - about the length of the last digit of my pinky finger when she was really stimulated.

I felt a new rush of excitement as I moved my hand down Ashley’s rib cage, truly exposing her chest for the first time. She grabbed the back of my head and pulled me in for a deep, passionate kiss as Bill muttered “holy fuck” under his breath. Encouraged by Ashley’s fervor and the thrill of our watcher, I slid my hand down her torso until I reached her always neatly trimmed mound. I ran my fingers gently through her short hairs as we continued to breath heavily into one another’s mouths, our tounges frantically twisting together.

She parted her legs slightly, the towel still covering her left thigh and pussy, and I slipped my middle finger gently between her lips, her hips bucking up slightly to meet it. As soon as I grazed her inner labia, any concerns I had about her feeling pressured or unduly uncomfortable slipped away. Ashley and I had never had to use lube; her body produced more than enough slickness on its own, but I had never felt her half as wet as she was now. I scooped some wetness from between her folds and slid it up to the hood of her clitoris, gently massaging her in a circular motion. The shutter from Bill’s camera fired a few more times.

“Jake, I’m going to need you to move your hand a little. You’re blocking everything,” Bill said. Upon hearing this, Ashley lifted her hips, ripped the towel from underneath her body, and tossed it to the ground next to the bed. She spread her legs giving Bill and the camera a full, unobstructed view of her womanhood. “Yesssss,” he hissed. (Click, wind, click, wind). I kissed down her neck to a spot above her collarbone that drives her crazy, noticing in the process that I could see her pulse in her carotid artery. She was a modest girl in normal life, she dressed conservatively and never showed off her body, even preferring one-piece swim suits, but she was loving this. “I’m throbbing,” she whispered in my ear.

A minute or two passed with me fingerling her softly while she slowly stroked my dick. “Ashley, do you like to give head?” Bill asked. She didn’t respond and, sensing her hesitation, I said “she’s not really a big fan of it, but she’ll do it from time to time.” The fact was I could count on one hand the number of times Ashley had given me a blowjob, none of them to completion. It just wasn’t her thing and I honestly didn’t hold it against her.

“Well, could this be one of those times?” Bill asked.

Ashley didn’t answer verbally but she pushed herself up and rolled us both over. She straddled my knees, grabbed the base of my cock, and absolutely devoured me. The vigor and speed with which she sucked me was like nothing she’d ever done before (and considering she was my first, nothing I’d ever experienced before). “Stick your ass in the air,” Bill commanded. She obliged (click, wind, click, wind). As I watched her mouth engulf my cock, I saw her hand reach between her legs to spread herself further for Bill’s lens. “Gorgeous,” he said. “Perfect,” (click, wind).

I wasn’t going to last at the rate and passion with which she was blowing me. I put my hands on the side of her face and gently pulled her in for a kiss. She shifted her body up mine and lowered herself slowly onto my cock. I grabbed her hips and held her still, worried that the slightest motion would force me to erupt inside of her. After catching our breaths, she began to slowly grind her clit on my pelvis before riding me in an up and down motion.

“Ashley, turn around, face toward me,” Bill directed. She slipped me out of her still gushing pussy, my dick glistening with her slickness, and faced Bill before reinserting me into her body. She leaned back toward me, giving me an opportunity to reach around and tease her nipples. She threw her head back and moaned (click, wind).

I was lost in pleasure, eyes closed as Ashley rode me slowly, when I heard Bill say, “wow, Ashley really knows what the camera wants!” I craned my neck to the side and could see in the mirror above the dresser behind Bill that Ashley was raising her hips until the head of my penis was just barely penetrating her hole while spreading her pussy lips with her fingers for the camera. Bill closed in as she slammed down on my cock before slowly repeating the tease, his camera lens maybe 6” from my girlfriend’s pussy (click, wind, click, wind).

“I’m going to need a new roll of film,” Bill said. “Let’s take a break for a second, then I want some shots of Ashley’s face as she cums.”

A thing about Ashley: she couldn’t cum from penetration alone. I usually simulated her clit with my thumb while we fucked to get her there until I got her a bullet vibrator for Valentine’s Day, which quickly became her favorite method of orgasming, second only to oral. After Bill finished changing the film roll, she looked me straight in the eye and said “I want your face between my legs.”

We rolled over again, her head on the pillow and me between her knees. Staring into her shimmering pussy, I could’ve came right then with no direct simulation, I was so turned on. I lowered myself and licked her outer lips before gently sucking on her labia. She squirmed and moaned as I took her clit between my lips, sucking it into my mouth while flicking across it with my tongue.

“Ashley, can you get those lovely nipples hard again?” Bill asked. Ashley rubbed her breasts and teased her own nipples, something I’d never seen her do before, and I found it incredibly hot. She bucked her hips into my face, forcing her clit deeper between my lips (click, wind, click, wind, click, wind).

Ashley always took a while to cum, and was a one-and-done kind of girl, but she always had incredibly powerful, leg-shaking orgasms when she got there. She had reassured me many times before that that was just the way her body worked and that I always pleasured her well. After a few more minutes of me lapping at her vagina, Bill repeated his request. “Ashley, hon, your nipples. Would it help if I turned the AC up?” “I’m already cold,” she said as she again teased her nips back to erection. After another couple of minutes she moaned “I think I’m getting close” and raised her hips again. I took her raised position as an opportunity to slip my middle and ring fingers into her vagina, stroking her g-spot.

With a hint of frustration, Bill again commented on the fact that her nipples had slightly softened. “Let me see if I can help,” he said as he walked to the side of the bed. He held the camera in one hand as he reached down and fondled her breasts before pinching her nipples back to attention, taking pictures of his own hand groping her. The moment he pinched her, she groaned “oh my god,” before clenching her thighs against my ears and jutting her hips back into my face, cumming hard, almost to the point of tears. Her legs quivered as she loosened their grip on my head and her stomach convulsed with spasms before she collapsed motionless. “That was incredible,” Bill stammered, his own cock visibly hard in his chinos.

After giving Ashley a moment to collect herself, Bill looked at me and said “alright, Jake, your turn.” I slid up Ashley’s body, positioning my tip back at her opening. She smiled as she gazed at me. “Fuck me,” she almost whined. Dirty talk was not one of our things at this stage. I found it foreign and extremely erotic. I slid into her drenched pussy and pounded her into the mattress as Bill was in constant motion snapping pictures one right after another. A close up of her face, an overhead shot holding the camera high to capture our entire bodies, another close up of my cock filling her hole, her clit as I held her lips open, a shot from behind. Despite having already came, Ashley moaned the most guttural, pleasurable sounds I’d ever heard her make.

I would like to say I gave her the dicking-down of her life. In reality, I lasted maybe two minutes, the eroticism, and passion, and naughtiness of the situation overcoming me. I pushed her knees up and opened them wide, bottoming out in the heaven that was her body before pulling out and absolutely drenching her taught, beautiful body from her mound to her neck. It was the most powerful orgasm I’d ever felt - 8 or 9 ropes of cum and more volume than I thought my balls were capable of producing. She giggled before pulling my head down for one last kiss.

“You two are fucking incredible,” Bill said as he took several last pictures of Ashley’s cum-soaked body.

Ashley showered before getting dressed. “I can drop you guys off wherever you need me to,” Bill said. “It’s fine, we can walk from here,” I replied.

A couple of weeks later, the phone rang at my mom’s house. “Jake! There’s some guy named Bill on the phone for you.” Bill met us back at the Dairy Queen to give us a copy of the pictures, which Ashley and I split between us. He asked when we’d like to do another session. “I’ll call you in a week or two,” I told him. I never did.

Ashley and I dated for another 6 months until we mutually and amicably parted ways after we left home for different universities. I ran into her at a bar about 10 years later back in our hometown. We shared a drink and talked about old times, but neither of us mentioned the photo shoot. She still was way out of my league.

I kept my half of the pictures for years as a fond memory of the hottest afternoon with my first real love. I finally shredded them shortly before my wife and I got engaged, but I still have those images burned into my mind. I sometimes wonder if Ashley still has her half.