It happened more than two weeks ago now, but still I can’t get it out of my head. It’s almost like it’s consumed me. The questions and self-doubt, the denial, the arousal, the insecurity, the confusion, it’s all still there like it just happened five minutes ago. So here I am baring my soul and my thoughts and feelings because I have nowhere else to turn. I guess getting fucked by a woman with a strap-on can do to do that to you.
Still, I’m not really sure what I hope to accomplish by sharing thoughts in my head, let alone sharing them on the internet. I guess I’m looking for some kind of understanding or a kind of reconciliation with myself. Or perhaps I’m hoping to find a kindred spirit or the insight of others. But writing it all down and sharing my experiences seems like a good a place as any to getting all those voices out of my head. So I don’t know if this is an essay or a diary or what. It’s probably more like a confessional than anything.
So where do I start? I guess the beginning is always a good place, and the beginning probably starts with me.
I’m thirty years old, college educated, and single. I’ve never been married, and I don’t have any kids, and I have really had only one serious relationship in my life. And that relationship ended about seven or eight years ago. In the time since I’ve dated occasionally, but nothing ever really took off. I’m not sure why, but I like to blame it on the fact that I’ve been focused on my career, and haven’t had time for a real relationship. Whether that’s true or not, I don’t know.
I like to consider myself a pretty normal guy. I’m goal oriented and driven. I grew up in a stable household and now live a comfortable, if relatively boring, life. I don’t consider myself overtly good looking, but I don’t consider myself unattractive either. I’m tall with a slender frame, closely cropped brown hair, fair skin, and greenish-blue eyes.
I’m not sure why I’m describing myself. Perhaps I’m being a bit defensive, and want to make sure and characterize myself as an average, ordinary guy. I can’t think of another reason, and either way, I’m not sure knowing much about me even matters.
I guess this whole saga started a few months ago. I’d known Rachel for probably about a year. I guess saying I knew of her is probably more accurate. I didn’t really know her per se, as I’d never formally met her, but from the first time I saw her from afar, she always caught my attention. Rachel worked for the same company as me, but as the company I work for occupies multiple floors of the same building, we rarely crossed paths. Still I found her attractive and was intrigued to know more. A few months ago, I finally got my chance when she switched departments. We still weren’t working directly together, but now our paths seemed to cross more often, and over time and through mutual acquaintances I got to know her a little.
Our relationship was nothing much really, just idle chit-chat about nothing, and a lunch outing or two along with other people from our office. I found out she was thirty-five and had been married before, but had been divorced for about five years now. She had an interesting personality. She was cordial and friendly, and polite, but at the same time she was up front and not afraid to speak her mind. As I got to know her over the course of a month or so, I found myself growing more and more attracted to her, both physically and otherwise. She just had this way about her. It’s hard to describe, but suffice it to say I was just drawn to her.
At that point, I really had no idea what she thought about me. I liked to think she felt some attraction toward me, but I couldn’t really tell. Part of me felt very uneasy around her. For some reason I was scared to let my attraction to her show. Still, I got the feeling that she knew, and seemed to be subtly flirting with me. In the back of my head though, I didn’t think the flirtation was real. Part of me thought it was just a game to her, and she liked the attention, the idea of me being enamored with her.
Over time though, the flirting definitely effected me. It was strange, my lack of self-confidence wouldn’t let me think her flirtation was real, but at the same time her backhanded attention just kind of sucked me in. It was weird, because the more she flirted, the more uneasy I felt. It was kind of like I was out of control. I felt so attracted to her, yet I barely knew her. It made me feel like I had no control over my own feelings, which was a very awkward position for me to be in.
Then about a month ago, we ended up together at a happy hour on a Friday night with a number of other coworkers. I was having a good time, and as usually happens after a couple of drinks, my inhibitions were a bit lowered. By happenstance, I happily found myself sitting at the bar next to Rachel, and before I knew it we were actually having a conversation. I was oblivious to everything else. I couldn’t believe I was actually talking to her. The conversation went well and in my mind we seemed to hit it off. It seemed to go so well, that before we even realized it, almost everyone else from our group had already left.
The next thing I knew, I was walking out to the parking lot with Rachel. We when got to her car, she kind of turned and smiled and in one fell swoop she was kissing me. It felt so good I was literally overwhelmed. It was exactly what I had dreamed about. I just closed my eyes and let the sensation wash over me not knowing where it would lead. I don’t know how long we stood there and kissed. Maybe a couple of minutes. Maybe five or ten. But slowly it got more heated. I know my brain was spinning a million different directions as she moved her hands over my chest and down across my stomach. I let out a gasp as her hand slid further down and across my cock. I’d been aroused all night, but now I was doubly so. As she let her fingers linger gently, I found myself opening my eyes to see her looking right back at me, a mischievous grin pursed on her lips.
Then almost as soon as it began, she pulled away, the smile never leaving her face. She said she had to get going as she slipped inside her car and drove off. I didn’t know what to think. I was left standing there dumbfounded. Had I done something wrong. Did she not like the way things were going. Was she taken back by my arousal? Was I not what she expected? Was she worried about the fact that we worked together?
Looking back on it now, I’m still confused by her actions. I don’t know what she was doing. As I said, in some ways it seemed like a game to her. She liked the power she knew she had over me. She liked pushing my buttons I guess. I didn’t realize it at the time, but now I know that I was playing right into her hands. She controlled everything. She had me wrapped around her little finger and I didn’t even know it. I was completely enamored with her. She had sucked me into her little world and there was nothing I could do about it.
Still, at the time I was dumbfounded. I spent the weekend agonizing over what happened. I was flooded with self-doubt. All kinds of thoughts invaded my head. Did she not like the way I responded to her? Was I too easy? Did she dislike the way I kissed? Did she just enjoy teasing me? Was I not well-enough endowed? I felt an amazing lack of self-confidence and I assumed the worst. A million different scenarios popped into my head, and none of them were good.
When Monday came, things were even stranger. She didn’t say a word about Friday night and neither did I. I was still too shaken and too worried. I couldn’t get her out of my head. She literally occupied every facet of my mind. And yet, she seemed to go about her business as if nothing unusual had happened. Her interaction with me was completely normal.
As for me, I was too scared to approach her or ask her what happened. I was so scared that would set her off, and that she would be done with me. I was so desperate not to let that happen. I wanted more than anything for what we started to continue. I didn’t want to do anything that might jeopardize that, and somehow I managed to convince myself that bringing it up would do just that.
So I agonized in silence for a week. For the entire week we went on as if nothing had happened. Our work relationship didn’t change a bit. It was like we were no closer than we were a month before. Cordial but distant friends. Still the dark thoughts kept creeping up on me. I wondered what she might be thinking. Whenever I saw her, I found myself almost staring, wondering what could be going in her mind. For the entire week, not five minutes passed where she wasn’t at the forefront of my mind.
The next weekend came and it was more of the same. I wallowed in self-doubt. Petrified to do anything but wait in agony. Wait for what, I had no idea. But there was nothing else I felt I could do.
Monday at work was the same thing. At least at first. But somehow I found myself alone with her in the break area. It was the first time we had really been alone since that night. I felt my stomach sink and my skin tingle. I was so nervous just being in her presence, I was scared I might do something to chase her away. She asked me how my weekend was and at least I managed to mumble an incoherent answer. I saw a hint of a smile from her. It made my mind race trying to decipher it, trying to catch some glimpse of what she really thought. But almost as quick as her smile came it disappeared. She offered information about how her weekend was, but I was too dumbstruck to really listen. But when she was done, she smiled again, and asked me what I was doing this weekend.
I think my jaw must have dropped to the floor as she kind of chuckled at my reaction. But before I knew it I had accepted her offer for dinner on Friday night. I don’t think I’d ever had quite such a mixture of relief and anxiety as I had in the moment she walked away. I still wasn’t quite sure what to think, and it wasn’t clear to me if she meant dinner as friends, or dinner as something else.
Friday seemed so far away and it loomed large on my mind all week. A million thoughts raced through my head as to where the evening might lead. It was so difficult for me to overcome my fear and self-doubt. I felt so intimidated and so in awe of her. I couldn’t remember a time when I felt such an attraction to a woman. But by Friday, I had at least managed to convince myself that our evening was a date and I wanted to treat it that way.
Dinner was good. Our conversation seemed to flow easily. I felt that uneasiness in the back of my mind, but for a while it seemed to dissipate. I felt so lucky to be there with her. I wanted to do everything to make sure the evening was perfect. I brought her flowers, and opened her car door, and pulled out her seat at dinner. I was the very definition of gentleman. She seemed to appreciate it, at least as far as I could tell from her smile.
After dinner as we made the way back to my car, we walked in silence. I opened the door for her and let her get inside. As I got in myself, I turned toward her and asked her if she wanted to get a cup of coffee. She didn’t respond right away. Instead, she gently slid her hand up and down my thigh, teasing me. As soon as I felt her touch, every inch of my skin was covered in goose bumps. It seemed like I became frozen solid when she asked if I wanted to go back to her place. At that point I think my mind actually exploded.
Back at her house I felt awkward. I felt unsure and out of my element, not that I was ever in my element with Rachel. But here that uneasiness seemed to flourish. Rachel on the other hand seemed confident and at ease. She seemed to ooze sexuality. Every move she made she seemed like she was floating, the way she carried herself was undeniable. I couldn’t take my eyes off of her. She fixed us each a glass of wine and then we took a seat next to each other on the couch.
She asked how I liked the wine and I mumbled an answer as I felt her hand slide down the length of my thigh. She wasted no time sliding her hand between my legs to feel my fully aroused cock. She asked how I liked it as she touched me gingerly. I couldn’t say a word. Instead I let out a low moan as my mouth dropped open and my eyes rolled back in my head. I didn’t respond or touch her. I felt like I couldn’t. It was strange but in a way I knew that she was in control and that wasn’t what she wanted. It seemed so easy and so obvious. I just had to sit there.
But then, just as gingerly as she was touching me, she got up from the couch and sauntered across the room. My eyes finally opened when she was several steps away. She simply looked back at me and I knew instinctively I was to follow.
What happened next was overwhelming to say the least. From my point of view, it was completely unexpected, and something that never even entered my mind. Part of me wonders how it happened and how she knew. Was it that obvious? Was I that weak? Was it so obvious to her that I was totally under her spell and completely under her control?
How was she so sure I wouldn’t balk? Does she do this to other men? Or was it something that was just obvious with me?
I found myself standing alone in the middle of her bedroom. Rachel sat on the edge of the bed, her eyes trained on me and a smile I’ll never forget across her lips. She told me to get undressed and that’s exactly what I did as I stood right in front of her. I felt so vulnerable, so exposed, so embarrassed. My hands seemed to tremble more and more as each article of clothing dropped to the floor. I felt so awkward and so uncomfortable standing there, completely naked, with her eyes focused on me and my aroused cock straining toward the ceiling. I wanted to cover myself, to turn away and hide, yet I couldn’t. Something was stopping me. I didn’t want to disappoint her. No matter how embarrassed I was at that moment, somehow I knew that disappointing her would be worse. So I just stood there trembling and totally naked, trying not to look at her as her smile and her eyes burned a hole in me.
I kept standing as she stood up herself, brushing by me on her way to the bathroom. For the next five minutes I stood completely alone and completely naked in the middle of the bedroom. I could hear her in the bathroom, but I didn’t dare move or say a word.
In five minutes she reappeared to find me standing exactly as she left me. Rachel however was completely different. The slinky black dress she wore to dinner was now gone. All that remained was a black push up bra and black thigh high stockings. When I saw her I felt my entire body shiver and shudder. I felt alarmed and terrified and unsure and awkward, not because of the situation, or because of her attire, but because of the strap-on fastened around her hips. It was a realistic cock, flesh colored and average sized, fastened to her in a black leather harness.
Seeing her that way was strange. It made her seem so powerful and so in control. The way she carried herself was unlike the way I had seen any woman carry herself before. Just by her walk you knew she was in charge.
She didn’t have to say a single word. I knew exactly what she wanted and exactly what to do. As she walked toward me I instinctively dropped to me knees in front of her. It felt uncomfortable and awkward to be in such a position, but at the same time, even though it’s embarrassing and hard to admit, it felt right too. As I looked up at her and took her cock into my mouth for the first time, I saw the desire and glee in her eyes, and I knew that I didn’t want to do anything to disappoint her. I felt this incredible urge to please her, to make her happy. I wanted her approval more than I wanted anything.
As her cock slid in and out of my mouth she started running her fingers through my hair. I closed my eyes as the situation overwhelmed me. She talked to me as I sucked her cock, teasing and taunting me. Part of me felt embarrassed and small and weak, the other part was resolved to please her even more.
The sensation of being on my knees in front of her was hard to describe. I felt feminine and unsure. But to me, there was something erotic about it as well. I’m not sure what it was exactly, maybe it was the feeling of being so out of control, or so utterly dominated. Maybe it was her, and the way she carried herself and the way she talked and the glee in her eyes. Maybe it was the sensation of her cock sliding in and out of my mouth, the feeling of my lips being stretched and the knowledge of her eyes looking down on me.
I knew there was more to come. My complete and utter submission was inevitable now. There was no turning back. If the sensation of being on my knees was embarrassing, it didn’t even compare to the utter embarrassment of being down on all fours. Vulnerable and exposed doesn’t begin to describe how I felt with her behind me, one hand on my ass, and the warm slippery sensation of the other spreading lubrication between my cheeks.
She told me how she had wanted to fuck me like this for a while now, and how she knew I wanted it too, even if I didn’t know it myself. I felt so weak and so out of control. I was totally out of sorts, almost as if someone else had inhabited my body. It’s hard for me to fathom or understand now, but in that instant I found myself begging her to fuck me.
I whimpered when she first entered me. The physical feeling was unlike anything I’d ever felt. A complex mixture of pleasure and pain. I grunted as she entered me again. I begged for more. She slapped me on the ass before thrusting again. Before long she had both hands on my hips, and she was fucking me harder and harder. I squealed, I whimpered, I grunted, and I groaned as she fucked me. I’d never made so much noise before. I’d never been reduced to making those sounds.
Again she talked as she fucked me, a bizarre blend of aggression and dominance. I wanted it so badly, I wanted her to fuck me as hard as she could. And fuck me she did. She slapped me on the ass one last time as she finally dismounted me. I was left gasping for breath and trembling and she ran her fingers gently up the length of my spine.
In the instant that she stood, it was like my whole world came crashing down. Never had I had a more emotional moment. Never had I felt such a wide range of emotions. Pick an emotion, any emotion, and I felt it. I didn’t know what to think. I was stunned. Exhausted. Overwhelmed. Weak. Confused. Never before had I had such an intense experience.
When it was over, she patted me on the head and flashed a satisfied smile as she stepped around me and made her way back to the bathroom. I spent the night in her bed, naked, lying next to her. She didn’t touch me as I fell asleep. In the morning I awoke to her mischievous and contented smile and the feeling of her hand on my growing cock. By the time I realized what was happening I was fully aroused and she stopped. Again she patted me on the head as she got up from the bed and stepped into the bathroom.
Soon afterwards, I got dressed and left, feeling more confused and overwhelmed and embarrassed than ever.
As I said, it’s been two weeks since then, and the experience still seems just as intense. I must have played it over in my head a thousand times since then, and I’m still not sure how to feel.
I’ve been filled with self-doubt. I’ve questioned my manhood and my desires. I keep imagining myself on my knees in front of her with her cock in my mouth, trying to understand the thoughts that were running through my head. I try to reconcile my masculinity with the image of me begging her to fuck me. It’s all a blur of self-doubt and insecurity. I wonder what she thinks. She hasn’t mentioned that night since, but every time I look at her now I swear I see that smile.
I feel so vulnerable and so embarrassed by what happened. I wonder if she’s told anyone else and I wonder how much they know and what they think of me. Sometimes it seems like everyone knows, as I desperately want to hide it. When people look at me at work, I inevitably think they know, and I wonder what they must be thinking as well.
At the same time when I think back and replay it in my head, I find myself aroused, and I wonder how it affected her, and what thoughts ran through her mind as she fucked me. Part of me doesn’t want to feel that arousal or to remember it as erotic. But I can’t help it, part of me knows it was.
I find that I keep coming back to the same question. What if the same situation arose again? Would I let it happen again, and more importantly, would I want it? But no matter how hard I try to convince myself otherwise, the answer is always the same. Yes.
– The End –