It was that magical time in life after school and before marriage, generally known as the “early 20s.” It was time in life marked by shitty apartments, 11 hour days at an entry level job, four nights a week at a bar, scrounging quarters for laundry and juggling multiple women, trying to decide which, if any, were marriage material.

In hindsight, I might have been the only one of my group of friends doing that. The rest seemed pretty settled, but none of them openly questioned me when I would bring a different woman out every other weekend. But honestly, most of my friends trend prudish, so maybe they were the outliers.

Anyway, the two women I was seeing during that time period were Stacy and Holly. They both vaguely knew of the other, and neither had a claim to exclusivity, so I didn’t think much of it. But, again, it may have been awkward for my roommates not knowing which they would be seeing in our kitchen wearing my tshirt on a Saturday morning.

Stacy, I knew, was the marrying type. She was blonde and curvy. She found work as a kindergarten teacher right after graduation, and came from a stable nuclear family. She was on a broad path that lead to a house in the suburbs, 2.5 kids, a 401k, and all the rest.

Holly was a little more mysterious. She had dark hair and wore dark clothes. She had the same curves, but dressed a little more provocatively. She had less job stability, but worked in a more innovative field. Her family relations were strained, to say the least, and she openly asserted her lack of desire for ever having kids. Rather than a house in the burbs, Holly’s path lead to a cool apartment in a popular neighborhood and a real urban existence.

Surprisingly though, or maybe not, their sexual habits didn’t quite match the external assumptions. Stacy, while coming across as the girl next door, was very open to experimentation and trying new things. She judged the kinks of others, but when alone wanted to try them out for herself. In the time that we were together she started expressing a desire to be with other women and to have group sex, which I never would have expected when I first met her. Holly on the other hand was more self-conscious, more nervous when it came to sex. She liked to keep the lights dim and dirty talk to a minimum.

This is all prelude to the last time Holly and I were together, when we decided to call it quits.

Her new job was sending her to a three-day training course in a city a few hours away. That meant that they were putting her up in a nice hotel, and even letting her stay an extra night after the training was completed. She was going on a Tuesday, and invited me to join her Friday afternoon, staying until Saturday. While we’d had many overnights together, this would be the first out of town trip, and the first hotel stay. (Staying in a hotel at all times got me very excited. Surely I’m not the only one…)

But a few weeks earlier, Stacy and I had had the conversation. We decided it was time to make it exclusive. That meant that it was time to say goodbye to Holly. I told her this the weekend before her trip, that I owed it to Stacy, and that I hoped we could still be friends. She took it surprisingly well, and insisted that I still come to visit her for that overnight. As friends.

I took that Friday afternoon off work and, with an overnight bag packed, drove the two hours to where Holly was staying. She finished her training for the day at 3:00 and suggested that I meet her in the hotel bar. I had just finished my first drink when she came in. She was wearing blue tights, a dark gray tweed skirt, white blouse (showing a black bra underneath) and black framed glasses. I had never seen her in glasses before. It was as if she intentionally chose this outfit to drive me crazy, which was a real possibility.

She sat at the table with me and we gave a friendly kiss of greeting. She ordered a drink and we talked about her new job and the training she had been undergoing. “Mostly corporate brainwashing,” she called it.

“But I’m really excited about this job. I think it’s gonna be great. And it seems like a lot of the people working here are like me.” That was when I noticed a small diamond stud nose piercing, also new and also very sexy, in my comment.

“Hey,” I said, pointing it out. “That’s new.”

She smiled and playfully batted my chest. “I was wondering how long it would take. I did that yesterday. One of my new co-workers has one and I decided that, since this company wasn’t afraid of stuff like that, I should go for it. Do you like it?”

If she only knew. I collected myself and replied “I really do. I’m actually really enjoying the whole outfit. Even the glasses. Corporate life suits you well.”

She blushed a bit, then put her hand on mine. “I’m glad you like it. I don’t think it’s a secret that I like that you’re attracted to me.” I wasn’t sure how to respond. I put my other hand on top of hers, gently caressing her hand and wrist. She continued “Being alone in this hotel the past few nights has let me think about a lot of stuff. I was thinking about how much of my life was about trying to make others happy, my parents, professors, employers, past boyfriends, and it just never seemed to be enough. Being with you, even though we kept it casual, I was always worried that I wasn’t keeping you happy, that you’d be disappointed too, and blame me for everything missing in your life.” I started to object but she stopped me and kept talking.

“No, it’s ok. I’ve finally come to that clichéd realization that you can’t please others until you please yourself. And I’ve got that now. I know how to do that, and I’m not going to be afraid anymore of being a little selfish and putting myself first.

“And that’s the real reason why I asked you to come visit me. I know what I want now, and I’m not worried about whether you want it or not. Tonight you’re gonna do what I want, and after tonight we will say goodbye for good.”

At this point, my other brain had fully taken over. Outside I kept calm, but inside I knew that I was in for a night of crazy sex with Holly, and I was totally ok with that. I eventually came up with a response that I felt met all the needs.

“I’m glad to hear that, and I want you to know that I’ve at all times been eager to do whatever it took to please you, even if I didn’t at all times make that clear. That was my mistake. And I appreciate one last opportunity to show you how wonderful and special I’ve at all times wondered you were.” Maybe laid it on a little thick, and the slightest arc of her eyebrow indicated that she might think the same, but that didn’t matter anymore.

We paid for our drinks and I grabbed my bag. She lead me to the elevator and pushed the button for the floor that she was staying on. We were alone in the elevator, and she silently stepped up to me and kissed me, first an innocent peck, then a nibble, then a hard bite on my lip. I flinched at the pain, and she laughed. “It’s about what I want” she said.

We exited the elevator and I followed her to her room. She walked in ahead of me and set her purse down on the dresser. I heard the door click closed behind me as I sat my bag down next to the closet. The room was dimly lit, with the north facing window showing the downtown skyline but not taking in any direct sun. She hadn’t turned on any lights, but there was just enough from the open window to navigate. There was a large bed, already made up by housekeeping, and a large chair in the corner, just big enough for two to cuddle up close. The bathroom featured a large walk-in shower with a corner seat.

She took off her glasses and set them next to her purse, then turned and stepped back toward me. She still hadn’t said a word. She paused just short of me, inches from my chest. She looked up at me with the same smile I always enjoyed, accented in my favorite dark red lipstick. Then to my surprise she reached back and slapped me hard across the face.

Before I could respond she slapped me again, harder, then pushed me back against the wall and pulled herself up my body, biting my lip again. Her hand grasped my groin through my jeans and her other hand pressed one finger to my lips. “You don’t speak unless I tell you to speak. Find out?” I nodded.

She took a step back and lifted her skirt up her thighs. The blue tights were actually thigh high stockings. She reached up and pulled down her black panties. She stepped out of them and balled them up in her fist. “Open.” I opened my mouth. She shoved them in my mouth, then gave me one more slap. “Don’t move.”

Not gonna lie, the taste of her panties in my mouth, the entire new attitude had me really excited. Which I guess was what she was going for. The only question in my mind was whether this was all part of an elaborate tease for my ending things with her, or if this really was going to be a wild, fun night.

She moved past me and took a small black bag out of the closet. This was separate from her larger suitcase which I also spied when I entered the room. She moved to the other side of the room and unzipped the back, using her body to block my view. She withdrew four black straps and tossed them onto the bed. “Attach one of those to each of the bed’s legs” she commanded. I stepped toward the bed and she immediately moved back, staying as far from me as the room would allow. I picked up the first strap and made sense of it. One end attached around the leg, the other end had a strong Velcro cuff that would go around a wrist or ankle, and there was a strap to tighten it to allow for as much or little range of motion as desired. I quickly attached all four, then moved back to my corner.

She was sitting in the chair in the corner, her legs curled up beneath her, a few buttons undone on her blouse. The small black bag lay on the floor next to her. “Good. Now strip. Then lay down.”

I did as I was told, slowly undressing and placing my folded clothes on the dresser. I laid on my back and spread my arms and legs, waiting for her to bind them. When I was settled, she got out of the chair and came to the bed, tightly binding first my feet, then my hands. I couldn’t move any of them more than a few inches.

She sat on the edge of the bed, facing away from me, and slowly unrolled the left stocking. Once removed, she reached back and teasingly dangled it over me, brushing it against my chest and face and throbbing cock. She released it and let it drift down half covering my face. Then she stood up on the bed, standing over me. She placed her right foot on the headboard and slowly rolled down the right stocking. She repeated the teasing then also dropped it over my face. I could still see, but everything had taken a light blue tint.

She moved to the window and turned to face me. She unbuttoned the rest of her blouse and let it fall to the floor. Then she undid the front hook bra and tossed it to the side. She stared at me while she massaged her breasts and pinched her nipples. She pinched one and pulled it hard, catching her breath, then loudly exhaling when she finally released it. She did the same to the other nipple. Then she pulled one up toward her mouth. It didn’t quite reach her tongue, but she let saliva spill out off her tongue and drip onto her nipple. She then spread the spit around until she was moaning and her knees were wobbling. She did the same to the other nipple, again needing to catch herself from falling.

She picked up the black bag and pulled out a short chain, on either end were metal clamps. She pinched her nipple, making it hard, and attached the first clamp. Then she repeated with the other. Once attached, the chain spanned her breasts. She gave it a tug and it held firm, sending a jolt through each breast.

“Don’t worry, you’ll get to wear it next.”

She moved closer to the bed and unzipped her skirt. It fell to the floor exposing her bare, hairless pussy. Her legs were parted and I could instantly smell how excited she was. She reached down with a finger and swiped off a few droplets, then brought it to my lips. She moved the stockings away and let them fall on the floor, then, without removing the panties from my mouth, wiped her wetness on my lips. She did this two more times, until she was certain that my lips were covered.

She went back to the small bag and took out a medium sized black ribbed dildo. She waved it at me, making sure that I got a good look at it. Then she climbed onto the bed, standing above me, her left hand bracing herself against the wall above the headboard while her right hand guided it into her wet pussy. She gave it several long, slow, deep strokes before taking it out and bringing it to her lips. She furiously sucked on it with more intensity than she had ever used on me.

She then squatted down so that her ass was just inches above my chest and her pussy was spread out in front of my face. The toy went back inside, and she proceeded to gaze into my eyes while fucking herself hard and making herself cum. When my gaze moved away from her eyes to between her legs, she let the spit drip down onto my face, then slapped me and exclaimed “Eyes up here.”

In the midst of her second orgasm, she quickly withdrew the dildo and proceeded to cover my face and chest with her squirt. This was something we had experienced a few times, but it was always a fluke. She had apparently learned exactly how to harness it and was now showing off.

She leaned close to my face and bit down on a bit of her panties which was sticking from my mouth. She withdrew them using only her teeth, then tossed them on the floor. Before I could close my mouth she spit into it and slapped me again. She wiped some of the wetness off my cheek and stuck her finger in my mouth to lick clean. Then she raised herself up and said “One more.” She slid the dildo back into her pussy, making herself cum one more time. Then slid the dildo into my mouth. Without her telling me what to do, I sucked it off the best I could.

She laid on top of me for a few minutes, then rose up and took another thing from the black bag. This was a bottle of lubricant. She squirted some into her hand, then proceeded to rub it over my cock, using much more than I thought was necessary. She squirted more into her hand and bent over. She reached down deep between her legs, past her pussy, and rubbed the lube into her ass. She was obviously enjoying the sensation and frankly probably didn’t need me at the moment. Nevertheless, she climbed up on the bed again and slowly lowered herself onto my cock.

Anal sex was never something that she had brought up, nor had I. It was something I enjoyed, but never demanded, and I figure if she ever wanted more than the occasional finger or tongue she would have told me. It occurred to me that this was her way of telling me.

She easily slid down until I was completely inside her. “Fuck….” She gasped, then leaned forward, “Good thing I’ve been practicing.” She continued to slide up and down on my cock, squeezing me until I couldn’t take it any more. I couldn’t hold back the groans and grunts, and she knew what was going to happen. She took me deep and whispered “ask for permission.”

I gasped and yelled “Please let me cum in your ass!”

“Ask nicer.”

“Please Holly, please let me fill your wonderful delicious ass with my cum. You are so wonderful and you feel so good I cannot stop.” Before she could respond I exploded. Spurt after spurt filled her, and I felt her clenching down on me in rhythm.

After my orgasm subsided, she raised herself off me and straddled my chest. “I didn’t give you permission. So now you know what you should do.” I didn’t actually, but she quickly put an end to that. She moved herself over my face and lowered her ass onto my mouth. With her thighs pressed against the side of my head, I could faintly hear her say “clean it up.”

I was repulsed at first, but also realized that there was no way to half-ass my way out of this (pardon the pun). I started tentatively, then proceeded to treat her like a feedbag. Soon she was thrusting her hips and begging me to keep going. I could hear the jangling of chain connecting her nipples, and I managed to work a free hand around to give it a tug, which elicited another squeal from her.

I guess I satisfied her, because she eventually stood up and left me alone while she went into the bathroom. I heard the shower run briefly while she washed herself. After a while she came back with a wet cloth which she used to wipe off my face and chest. She went back to the bathroom and came back with another wet cloth to clean off my now-soft cock. I hadn’t realized how much of a mess I’d made. Well, we’d made, I guess.

I wondered if she was going to untie me now, but she didn’t touch the bindings. “You’re doing so well,” she said, “but there’s still one more thing on my list. At this point she untied my ankles and lengthened the straps holding my arms. She grabbed my feet and pulled me down to the end of the bed. My arms were still mostly immobile, and my ass was on the edge of the foot of the bed. Me feet freely dangled down to the floor.

She went back to the small black bag and took out a blindfold. She held it up and then said, “No, I want you to see this.” She dropped it and then picked up the nipple clamps that she took off before her shower. She straddled me and proceeded to pinch and tease my nipples, making them hard enough to attach the clamps. Once done, she batted at the chain and made me yell out a few times.

“Because you’re being so good, I’m going to put these back on.” With that, she picked up her glasses off the dresser and put them on. She was so damn sexy in glasses. Totally worth it.

“But because you’re also so naughty, I have to put this on too.” I thought what she meant, when from the small black bag she withdrew a strapon dildo. It wasn’t any bigger than the dildo she made me lick clean earlier, but it was still bigger than anything I’ve had in me before. She beamed as she stepped into it and tightened the straps, then locked her eyes on mine as she covered it with lube, stroking it as if it were her own real cock.

She lifted my legs and spread more lube into my anus, letting her fingers linger. Then she wordlessly slid into me, slowly, teasingly withdrawing and slipping back in, over and over. My cock stiffened again, and she grasped it in her free hand and stroked it as she fucked me. Her speed built as did her force, gradually. Soon we were both passionately grunting with each thrust, and I felt another orgasm coming on, much more intense than the last. The strapon must have been rubbing her just right, because she was clearly about to cum again too.

She gave me permission to speak again. “Tell me when… I want you to cover my face…” That was all I needed to hear. I let out a gasp and shouted “Now… fuck…now…”. She gave one more deep thrust and without withdrawing leaned forward toward my cock. She gave it a few more strokes and I exploded up onto her face, covering her chin and lips and those sexy glasses.

“Yes… yes… cum on my face” she shouted with each spurt striking her dead center. Then she withdrew the strapon and completely lowered herself, taking me into her mouth.

She slid up my body, giving the nipple clamps a few more tugs, before giving me a deep, passionate kiss. She untied my hands and let me wrap my arms around her. I held her for a while and we kissed more and touched each others’ soft, sweaty, sticky bodies. Soon we dragged each other to the shower where we took our time sensually, almost ritualistically washing the other’s body.

The bed was completely ruined. We cleaned up the best we could, but there was no way it could be slept on. We got dressed and packed up the naughty toys, then left a twenty on the dresser. We stopped in the lobby to request a housekeeping visit, then left the hotel and walked hand in hand down the street for a late meal.