This story contains strong language (L).
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Note to Reader: The below events happened 18 years ago. While there is much about this story I remember quite vividly, I don’t recall every detail and have taken the liberty of adding details where memories are foggy.
It was about a week before Christmas in 2002. Lauren, age 28, and I, 29, had been married for a year and a half. We had headed to downtown Chicago, a great “Christmas city,” for a weekend getaway to enjoy the season and each other. At the time, she was in her surgical residency outside of Chicago, and we didn’t have much money. So, this trip to the Windy City to stay in a luxury hotel on Michigan Avenue, compliments of her sympathetic parents, had us quite excited.
In the early years of marriage, our sex life could have been described as having many peaks and valleys. During her residency and fellowship, Lauren worked long hours, logged many overnight shifts in the hospital, and often was on-call. Sometimes, weeks passed with no sex. Occasionally, our marriage felt like ships passing in the night as I came home from work just as she was leaving for the hospital to do another overnight.
The early years were hard years, and yet the love between us endured and strengthened. I often masturbated to stay sane during the many dry spells. Occasionally, we had phone sex. When we actually had time together, the sex was incredible—sometimes three or four times in a single day.
Our weekend in Chicago would afford much-needed time to reconnect, enjoy some luxury, sleep…and fuck (a lot). She had been teasing me as we drove into town, and at one point, had my erect dick in her hand. We had both dressed for a night out, but she was dressed to the nines. She wore a tight red dress with a low cut neckline to show some cleavage along with black thigh-high stockings and a matching garter belt—no panties. She looked so sexy, and I wanted her badly! As we drove into the city, hot and horny for each other, she slid her dress up just enough to allow me to finger her dripping wet pussy.
Getting out of our car at the valet drop-off, the sexual energy between us felt electric. In the lobby, after taking off her coat, she caught some looks—not only from men, but also women who admired this strikingly beautiful, elegant, 5’10” young woman with long, firm curves and lovely breasts, all hugged perfectly by her red dress. Stepping into the elevator to go to our room, I nearly shook with excitement about all to come (pun intended) once the door to our suite closed.
Oh, our room… Young couple that we were, we found ourselves smitten by our luxury digs. They exuded lushness, comfort, and downright extravagance. After we dropped our bags on the floor, Lauren walked over to the very large floor-to-ceiling, wall-to-wall window and pulled back the curtains to take in the vista from above. She held a glass of wine in her hand, as we’d stopped at the bar in the lobby to buy a few bottles. In a hotel across from us in the dark night, we noticed people milling about in their rooms. Sitting at a small table as we enjoyed the view, we drank a few glasses of cabernet sauvignon. Very soon, we felt quite buzzed and even hornier for each other. I told her how hot she looked, how sexy her dress was, how much I desired her and, yes, how much I wanted to fuck her.
I asked Lauren to stand in front of the window, and she did with a somewhat puzzled look on her face. I got behind her, fondling her marvelous breasts—far more than a handful. She whimpered as I kissed the back of her neck. I pulled her red, skin-tight dress down and off of her and unclipped her Victoria’s Secret push-up bra, exposing her naked body right there in front of the window. All she still had on were the garter belt and black thigh-high stockings. I stroked her absolutely dripping wet pussy. We were both a little drunk, and the sexual desire between us was so strong that I remember thinking at that moment anything could happen.
With our lights on, the curtains totally pulled back, and it being nighttime, we both knew all that was happening between us in our room could be seen by those in the hotel across the street (if they were, in fact, looking). Lauren giggled and suggested we close the curtains, but I could tell she didn’t really mean it—she wanted the curtains open. “Even if they’re watching, we’re anonymous in this huge city, and you could be the star of this show for them,” I remember saying. She smiled, and I could tell she was intrigued. (Remember: in 2002, there were no mobile phones to shoot videos, take photos, etc.)
“So put on a show for them?” she asked with a smile on her face, pointing across the street.
“Yeah,” I replied.
She smirked in a playful way. “Should we really do this?”
“We’re anonymous, baby.”
Silence reigned for about ten seconds as she processed the moment… and opportunity.
“Okay,” she said with a measure of glee.
In those early years of our marriage, we’d occasionally ventured into exhibitionism. We both have an exhibitionistic streak. For instance, I often bought—and still buy for her—revealing clothing (e.g., the red dress) and skimpy swimsuits. Then, what started as naughty photos morphed into graphic sex tapes (most of them show no faces). Looking back on it, I feel a tinge of guilt because the exhibitionism really was more about feeling like we were entertaining others than being intimate together. I loved her deeply, but I found sexual pleasure in opportunities to reveal her to others, and she seemed to welcome those moments.
In the hotel room, this was one of those moments. She turned around to face me, completely nude and with her perfectly firm, round ass to the window, and watched me as I took off my clothes. I imagined someone in the hotel across the street watching this gorgeous woman—my woman—through the window.
I was now completely undressed and my cock hard as steel. She stood at the window, stroking her clitoris, as I admired her while pleasuring myself. She had only recently started shaving her pussy bald, and it drove me wild! She walked over to me, and I cupped her breasts as I kissed and sucked on her pink nipples while she ran her hands through my hair. She dropped to her knees between my legs, and then my 28-year-old wife consumed my cock in her hungry mouth, our eyes locked on each other. The way she was sucking me off, I’d make it no more than five minutes before erupting in her mouth. We wanted to put on a show, so I needed to last longer.
I pulled her up on the bed, and we got into 69, our favorite position in those years. I sank my tongue into her sopping-wet vagina and pleasured her swollen clitoris as she once again took my rod deep, deep, deep into her warm mouth. I imagined onlookers in the hotel across from us looking on at this young couple putting on a show for them.
I pushed her off and got on my knees, stroking my cock as a clear invitation for her to get into doggy-style position. The way we were angled, any observers could see a full sideways view of us in this position. I slid inside her—Lauren responding with a whimper—and she dropped to her elbows, allowing me to go deep with every thrust. I cupped her round, firm ass cheeks with my hands and proceeded to fuck her just the way she prefers it: hard and deep. She moaned from the second I entered her.
“Are they watching?” I asked her.
Almost reflexively, Lauren looked out the window.
“Do you want that?” she replied, breathing heavily.
“I asked you first,” I retorted, pile-driving her pussy.
She giggled. We often like to have playful conversations while making love. A few seconds passed, then I slapped one of her ass cheeks.
“Yes,” she whimpered.
“Yes, you want to them to watch, or yes, you liked that?” I queried, hoping for a yes, she wanted them to watch. I spanked her again.
“Yes, I want them to watch,” she responded, still whimpering and now massaging her clitoris.
Another spank caused her to squeal. She’s always loved to be spanked when we did it doggy style.
Silence passed as we enjoyed this steady and deep intercourse with the erotic twist of allowing others to look on if they wanted. The sexual intensity built with every plunge deep inside her. I continued to cup her ass cheeks and focused on powerfully driving all of my manhood in and out of her. Her moans, her wetness, and the sloshing sounds of soaked vaginal sex revealed that she’d arrived at that state of extraordinary human pleasure: orgasm.
It was during her orgasm that suddenly, out of nowhere, I felt a jolt of shame—shame that we’d pulled the curtains open to be seen. I felt a bit scared. Would they (onlookers) find us after tonight? Was the promise of anonymity I’d made to my wife when we got into this with the curtains open false? Was this serving to objectify my wife? Was someone who knew us watching? Who was watching?
“Should we pull the curtains shut?” I asked her, feeling so flustered.
A few seconds of silence passed as she was just now coming down from her orgasm.
“What?” she replied, almost out of breath and sounding annoyed.
“The curtains… should we pull them shut?” I repeated.
Silence… only breathing, whimpers, and moans.
“If you want…,” she whispered back. And then:
“Keep them open,” she added.
I looked over at the window, still fucking Lauren as hard as I could. I felt certain we were being watched. I knew in my bones many were watching. I worried they’d find out who we were. But this felt so good. She loved it. And this was so naughty and bad.
“What if they’re watching?” I asked Lauren.
“Let them,” she answered back, almost unflinchingly.
I was close to cumming, and right then she began to orgasm again.
My moment of clarity quickly got overwhelmed by sexual ecstasy. I couldn’t hold it in any longer. I looked over at the window, sure this was all being seen, hoping we’d never be discovered after this moment. I cupped her ass cheeks hard and pumped her with my semen.
“Oh yeah, baby,” she said as she felt my load being shot inside her.
I stayed in her for a few seconds and collapsed on her back. We were both sweaty, and the room smelled of sex.
I got up and pulled the curtain shut, looking out quickly to see if anyone was watching. I saw nothing but a building mostly sheathed in darkness.
And then we showered and headed to dinner.
To this day, it remains Lauren’s and my favorite night of our marriage. We are certain we entertained others. The guilt I felt in the moment is not something I still feel about that night, but I felt it in the moment when I had that flash of clarity. We’ve talked about recreating the night but, in the age of mobile phones, know it’s not a good idea. Perhaps we could wear masks? Yes, we’ve actually entertained that thought.
And the red dress? She still has it.
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