I don’t really think of myself as a whore. I don’t think that I seem like one. So it was a little surprising when someone offered me money to have sex with him. The offer seemed to come out of nowhere. It took me off guard and because it was so sudden, I really didn’t take it seriously. The funny thing about it was that the offer came from someone I used to babysit while I was in high school.
I ran into Michael at the library where I was studying for class. He had just started college and saw me sitting alone with a pile of books, so he came and sat with me. I was 6 years older than him, but I had taken some time off from college, so he had a chance to start college before I finished. So now we were going to college together. I was happy for him because I know that financially, he had to be having a difficult time paying for college. It was nice to see him, and I was happy that he came over to sit with me.
I started babysitting Michael and his younger sister, Jill, when I was 16. His mother, Laura, was working as a nurse and after she got divorced, she needed someone to come over to their house and take care of Michael and Jill for a few hours in the evening. I would generally cook their dinner, do some house cleaning and help Michael and Jill with their homework. If they got their homework done early we would play video games until Laura got home from work. It wasn’t a very hard job and I didn’t make much money doing it. It was just nice having something to do after school and Michael and Jill were easy to look after.
In my mind, Michael, though he was now an adult and in his first year of college, was still the kid that I was hired to take care of. I wasn’t too surprised when Michael told me that he had the biggest crush on me back when I used to babysit him. I’m sure he had a crush on a lot of older girls that he knew back then. I was a little bit stunned, though, when Michael told me that he wished that he could have had sex with me. I was a bit surprised that he was so straightforward with me about something like that. I was embarrassed.
I blushed pretty deeply when he told me that, but I assured him that I couldn’t have had sex with him back then because he was just a kid. He just smiled looking at me and asked, “What about now?”
I was a little shocked by how forward Michael was being. I can’t imagine that he learned to talk to women like that from his mother. Fighting back my total embarrassment, I responded back by asking him, “Do you want to get slapped?”
Michael apologized. I wasn’t sure if he was really sorry. I don’t know if Michael even knew what he should be sorry for. I kind of felt bad for him. He had somehow managed some misplaced confidence, but I had a sense that behind it he was still worried about how I would respond. I didn’t want to destroy his ego, but his advance just didn’t seem appropriate given that I used to be his babysitter. Then he asked the question I really wasn’t expecting. He asked, “What if I paid you?”
At first I didn’t know what to say. I thought if I just rejected his offer completely, he would just keep trying to talk me into it. I decided that I would counter his offer with something that he couldn’t possibly afford. I would make it so ridiculous that he would just give up the whole idea. If he tried to say that I was asking for too much, I would just pretend to be offended that he didn’t think I was worth it and accuse him of not being honest when he said he had a crush on me. It seemed like a good plan. So I told him that if he put a thousand dollars on my Cash App, I would go to his house and have sex with him.
I thought for sure that would put an end to the whole thing. I don’t think that Michael had anything more than a part-time job. There was no way that he was going to come up with a thousand dollars. Even if he had that much money, I had doubted he would waste that much money just to have sex with me. That wouldn’t even make sense. I was right though. He didn’t have that much money. He wasn’t insulting about it. He didn’t tell me I wasn’t worth that much. All he said was that it would take him some time to get that much money.
I felt pretty awkward giving him the cash tab for my Cash App account, but I felt pretty confident that he wasn’t going to be able to come up with a thousand dollars. Even if he did, I just felt that he would realize that was a lot of money to just throw away on something like this. I felt like I just found a way to gracefully decline Michael’s offer, but Michael looked like I just agreed to the whole thing. At any rate, I felt like the matter was resolved without me needing to hurt Michael’s feelings. I was relieved about that.
A few days went by after my conversation with Michael. I didn’t forget about our conversation, but I wasn’t thinking about it either. I was nearly finished with my last class of the day. I felt my phone vibrate so I took a quick look at it. I had a notification on the screen and couldn’t believe what I was seeing. I just received a thousand dollars on my Cash App. Suddenly, there I was, sitting in class, my heart racing and dreading the message that I knew I was going to get. I was afraid of what the message was going to say, but I was also suddenly afraid of what my answer was going to be. And then I saw it. Suddenly on my screen was the text message from Michael. All it said was, “Can you come over at 4 PM?”
I took a few minutes to think about my answer. After a couple of awkward minutes, all I said was, “Yes.”
I was shocked and my heart was suddenly racing. I couldn’t believe this was happening. I couldn’t believe that Michael was able to come up with a thousand dollars and that he would just send it to me on my Cash App. There was nothing to stop me from keeping the money and just not show up. There was nothing to stop me from giving the money back. I could have at least done that. Somehow, Michael knew that I wouldn’t do either one. And then the realization sank in. Michael had just bought me. I had just sold myself to him.
I left class a few minutes early and rushed home. I wanted to freshen up. I wasn’t sweaty or dirty or anything but I wanted to look nice and be fresh and ready for when I got to Michael’s house. I took a quick shower when I got home and put on some makeup. I didn’t get too fancy. Just something to bring out my eyes and some lipstick. Then it occurred to me. I didn’t know how Michael wanted me to look. I was strangely worried that I wasn’t going to appear the way that he wanted me to look. I was suddenly amazed at myself. I was wanting to dress up for Michael and I was worried that he might want me to dress all slutty for him and I didn’t even ask.
I decided not to get too fancy or slutty. He paid for me, so he would get the slightly more dressed-up version of me that he would normally see. I put on a sundress, with only a bra and panties underneath. No sexy stockings or lingerie or anything like that. I didn’t even have anything like that. Most of the guys I date have pretty simple expectations and I have pretty simple expectations of them. This was really the first date I would ever go on where I was going to worry about expectations. It’s funny that I was even considering this a date. As far as I knew, this was just going to be sex, and yet I was worried about how I looked. More worried than I would have been if this was prom night.
After looking at myself one last time in the mirror, I left for Michael’s house. I decided to walk since he lived only a few blocks away. His mom somehow managed to keep the house after the divorce, which must have been difficult to do in our neighborhood on one income. Michael was still living at home. His sister was still in high school, and his mom was still working as a nurse at one of the hospitals in town.
It didn’t take long before I was standing on the front porch of their house. I knocked on the door and was soon slightly horrified. I tried not to show it. Jill answered the door. She smiled and rushed towards me and gave me a big hug. She told me how awesome it was that I came over to help Michael with his homework. I was completely embarrassed. I hugged her back and told her how great it was to see her again, as if I wasn’t there to have sex with her brother, for money.
Jill invited me in and explained that Michael just got out of the shower and was getting dressed. I kind of laughed at our sudden mutual obsession with our personal hygiene. I was also kind of happy about that. I doubt Michael with have been filthy or unpleasant smelling, but the fact that he wanted to shower before having sex with me kind of indicated that he cared how I felt. I hadn’t really thought about that before I got there, but his consideration of my feelings actually meant a lot to me. Considering why I was there, it shouldn’t have mattered, but it did.
When Michael finally appeared, I was sitting on the couch in their living room talking to Jill. As Michael entered the room, I stood up and gave Michael a hug. He gave me a tight hug in return and told me how happy he was that I was there. I kind of felt bad. I would have gladly come over to his house to help him with his homework if he had asked me to. I would have even done that for Jill. But that wasn’t why I was there, and I almost felt like I didn’t deserve to be greeted with kindness. I was there to have sex with him because he paid me. Michael’s kindness suddenly caused me to feel an odd sense of shame.
Michael asked me if I wanted to talk to Jill before we got started. I wasn’t really sure what to say. I didn’t want to be rude to Jill. We really hadn’t had much of an opportunity to talk since I stopped babysitting her and her brother. I was nervous about the prospect of having sex with Michael, which I knew would be happening soon, but I wasn’t trying to put it off either. I was relieved when Jill said that was okay, we could talk later. I knew deep down that the longer it took before we got to Michael’s room, the more nervous I would get about it.
With Jill excusing us from further conversation until later, Michael escorted me to his bedroom. A thousand scenarios of what was going to happen raced through my brain as we entered the bedroom. Everything ranging from running away embarrassed and ashamed to being consensually raped passed through my imagination. As Michael closed the door, he smiled nervously at me and asked me how we should get started. I was a little surprised by the question. I assumed that he would tell me how we were getting started and what he wanted me to do.
I was a little surprised, shocked actually when I asked him what he wanted me to do. His earlier confidence completely dissolved and turned into a look of complete humiliation when he told me, “I don’t know, I’ve never done this before.”
I wanted to be sensitive to his feelings when I responded. The situation I was in was extremely awkward and there was an element of shame that I was still feeling even then, but I still felt a certain sense of concern for Michael as though I was still caring for him. I suppose it may have been some leftover sense of responsibility for Michael from when I was his babysitter, but I didn’t want to see him in distress. I asked as gently as I could, “Do you mean with me, like this? Or with a girl?”
When Michael told me that he had never had sex and this would be his first time, I immediately flashed back to my first time. My boyfriend was not very gentle. Not out of cruelty or anything like that. He just didn’t know how to be gentle or how to take his time. My first time had been rushed, awkward, and very painful. The only good thing about my first time was that it was over quickly. As I thought to myself about my first time, it occurred to me that perhaps this was an opportunity to show Michael what I wish my boyfriend would have known when we first had sex.
I asked Michael if he had ever kissed a girl. Suddenly shy, he told me that he had. I asked him if he wanted to kiss me. He looked anxious and hesitant at the same time and told me that he wanted to kiss me more than anything in the whole world. It was touching in a strange way. He had paid to have sex with me but was somehow still waiting for me to consent to it. It also seemed as if he needed me to guide him through it. And I found myself wanting to teach him. I wanted to teach him how to have sex with me.
I was a little surprised by the feeling that I was having. I was conflicted and confused by my own thoughts as they were racing through my brain, processing what was happening. I was reconciling the idea that I was going to be having sex with someone that I ordinarily wouldn’t have considered having sex with. Not only was I going to have sex with him, now I was going to have to be his guide. And as I realized this, I also understood that I wanted to be careful not to embarrass him. Even though I was going to be teaching him something incredibly intimate and potentially awkward for him, I wanted him to still feel respected.
I heard my voice tremble just a little bit, not necessarily because I was nervous, but also because I couldn’t believe what I was saying, and also because I wanted to say it right. I looked up at Michael as he grinned nervously at me, and I asked, “Michael, will you please kiss me?” Michael looked visibly nervous when he leaned towards me. I closed my eyes and raised my lips up towards his. As I felt his lips touch mine, I felt his arms wrap around me pulling me towards him. I wrapped my arms up under his and up behind his shoulders, pulling him closer as I parted my lips. Michael was gentle and somewhat tentative as I felt our lips come together. Our first kiss was somewhat brief, but surprisingly nice.
As our lips parted from each other’s, I looked up at Michael and saw that he had this incredibly sweet grin on his face. I told Michael that I wanted to show him something. Our kiss was incredibly nice, but I wanted to show him more. I asked him to kiss me again but told him that this time I wanted him to let me slide my tongue against his. He smiled with a surprised look on his face and said, “Really?”
I smiled back and said, “Yes.”
He leaned towards me again and kissed me like before. I felt his lips part as I parted mine. I slid my tongue under his as I felt his tongue slide slightly into my mouth. As I slid my tongue against his, I gently massaged the underside of his tongue with my own as we kissed. I sensed that Michael was growing more comfortable as we were kissing. His tongue began to mimic the movements of my own, moving underneath my own tongue and reciprocating the sensations I hoped that I was giving him.
This kiss lasted a bit longer than our first kiss. As I loosened my hold on Michael’s body, he seemed to understand and broke off from kissing me and loosened his embrace somewhat. Things were progressing nicely and I felt my mood shifting. I wasn’t embarrassed anymore by the thought of having sex with Michael. I was strangely proud of myself. I was proud that somehow, he wanted this to happen with me.
Somehow, he knew that I wouldn’t try to embarrass him when he asked me. As awkward as it was when he initially mentioned what he wanted to do with me, I now realized that he trusted me to be sensitive about it. As my mood began to shift, I felt a sense of responsibility growing within myself. I wanted to please him, not because he paid me. I wanted to please him because I truly cared for him. Maybe not as a boyfriend or someone that I was romantically involved with, but because of something on a deeper level that I didn’t quite comprehend fully.
As we broke off our kiss, I asked Michael if he wanted to lay down in bed. He gave me a worried look. I asked him what was wrong. Michael suddenly had a fearful expression on his face and told me that he forgot to get condoms. I raised my wrist so that he could see it and pointed to the tiny little tube implanted under the skin. Michael didn’t understand at first, but I told him that my Nexplanon implant would keep me from getting pregnant. He was relieved when I told him that it was alright. Normally, if I was going to have sex with someone that I didn’t know very well, I’d insist they wear a condom to avoid STD’s but I was pretty sure he would say something if he had an STD.
As I sat down on his bed, I laid backward, still holding Michael’s hand. I carefully guided Michael on top of me and asked him to kiss me like before. Once again, our lips came together and parted. As his tongue began to explore mine as I guided his hand to my breast. As his hand began to feel and explore my breasts, he began to pull at my dress. I whispered in his ear, “Please unzip me.” He immediately reached behind me and unzipped my dress. He anxiously pulled my dress downward, exposing my bra. With some newfound confidence, Michael pulled my bra straps downward without me needing to tell him to. His lips abandoned my lips and suddenly I felt them in one of my breasts, pulling my nipple into his mouth. I was already aroused at this point but the feeling of my nipple being sucked into his mouth sent a shudder through my body.
As I felt my own arousal growing within me, I also became aware of Michael’s arousal. His fully erect penis was straining against his pants and was pressing against me. I wanted him inside of me but I also knew that was going to be disappointing for me and more importantly, it might be embarrassing for Michael. If I had simply let Michael put his penis inside of me there was a chance that he would cum all over me before he got a chance to actually be inside of me. I knew he would probably cum immediately after putting his penis inside of me and I knew if he came inside me, he would be finished. I didn’t want this to end like that.
As he was sucking on my breasts, I took his head in my hands and drew him back towards my lips. As he glanced up at me I asked him, “Would it be alright if I sucked your cock?”
His smile was so sweet as he told me, “Yes,” but warned me that he was afraid that he would cum in my mouth.
I just smiled back at him and told him, “I know, it’s alright.”
I felt a sense of urgency, and I rolled off the bed. Michael raised his hips up off the bed as I unfastened his pants and yanked them down. I told Michael to just relax, and he laid back on the bed, with his legs hanging over the side, with me kneeling between them. As I gazed down at Michael’s penis, I could see that the head was already glistening with pre-cum. I was thankful for the generous amount that was already coating the head of his penis. While I was generally not very fond of the taste of semen, I actually love the taste of pre-cum and the way it feels slick in the back of my mouth.
I looked at Michael and saw that he was looking up at the ceiling. And then I lowered my head and took his penis in my mouth. I would normally play with it first, but I didn’t think that would be a good thing to do this time. Instead, I immediately wrapped my lips around it and began to suck on his penis as if I were starving for it. Michael’s response was almost immediate. His breathing began to get erratic and his body began to spasm. I don’t know if he was even aware of it when his hand suddenly grasped my hair. Suddenly, my mouth was full of hot, slimy semen. I backed his penis partially out of my mouth so that only the the head was still in to allow more room for his cum. I struggled to swallow his semen as his penis continued to pulse and fill my mouth. Finally, the pulsing faded and his penis slowly began to grow slightly flaccid.
As Michael’s penis left my mouth, I looked up at him. He had a somewhat bewildered look on his face as he reached his hands towards me as I knelt between his legs beckoning me to lie next to him. As I settled into bed next to him, Michael told me that he felt bad. I asked him why and he told me that he really wanted to have sex with me. He seemed to be relieved when I told him that we weren’t finished yet. We were still going to have sex.
As Michael and I shifted positions so that our heads were resting together on his pillows, Michael resumed holding me in his arms. I was touched by his concern when he told me that he wanted me to enjoy this too. It was surprising in a way. He had paid for me. My feelings were irrelevant. At least they could have been. Maybe they should have been. But they weren’t. Not to Michael and in a way, I loved him for that.
Michael probably wasn’t aware of it, but I believed it to be true, and that was that Michael would probably be ready to have sex again soon, but in the meantime, I felt like he needed something to keep his mind on enjoying the moment. Knowing that he wanted me to enjoy this I asked him, “Do you want to do something for me?”\
He smiled and asked me, “Do you want me to go down on you?”
Michael looked surprised when I told him, “No, this is better.”
As I slid my dress completely off, followed by my panties, Michael looked at me, mystified, as if he was going to learn some ancient secret. After laying back down next to him, I asked Michael if he remembered how as a kid, he would make a gun with his hands? He seemed confused, and I reminded him as I made a fist for him, and then pointed my thumb upwards and then the two fingers pointing outwards, and told him, “See? A gun.”
He smirked and said, “Oh, ok?” Then he made a finger gun like the one that I just demonstrated for him.
As Michael held out his hand, now made into the finger gun like I showed him, I took his hand in mine, and directed it between my legs. Michaels seemed to understand what I was wanting as I pointed his fingers towards the entrance to my vagina and laid back, opening my legs up wider for him. The sensation was amazing as I felt his fingers enter me. Michael smiled and told me he couldn’t believe how warm I was inside. I asked him if he noticed that he could feel my pelvic bone inside me and he told me he thought he could. I told him it would feel amazing for me if he would use his fingers to push just a little past that and massage me there with his fingers. He did as I asked. As his fingers moved in and out, massaging that spot, I reached down with my hands, searching for his thumb. As I found his thumb, I directed it to my clit and asked him to gently stroke there with his thumb.
Michael seemed eager to follow my instructions as I guided him through how to touch me. The rhythm of his fingers and thumb were increasingly only half from him. As the sensations began to build within me, I found myself pushing back against his hand uncontrollably. Michael was literally taking my breath away as I began to take deeper and deeper breaths, trying and finally failing to keep silent so as not to alert Jill as to what was happening. As I heard myself sigh, I reached out and pulled Michael towards me. I began kissing him. Not like before. I was kissing him more urgently. My body desperately wanted his, needed his, and I began to spasm inside. I held Michael in a tight embrace, desperately kissing him as my body continued to convulse.
My mind was lost in the sensation. Michael had just brought me to orgasm, and it was as if I was taken over by an intensely powerful dream that was causing unbelievable sensations inside of me. I continued to hold onto Michael tightly as the feelings built, shattering me in an intense overwhelming force and then slowly faded. My mind became once again capable of forming a thought and I found myself recovering in Michael’s arms as he held me, I felt happy for Michael and an inexplicable sense of pride in myself.
I found myself reflecting back on the first time I had sex. Neither my boyfriend nor I had ever had sex before, and our first time wasn’t pleasant, at least not for me. Michael's first time was different. When we kissed, it wasn’t clumsy or awkward. It was sweet and he let me guide him. We both now have had orgasms, and we haven’t even had sex yet. When I had sex for the first time, my boyfriend’s orgasm was almost immediate, and the only thing I felt was a mess between my legs. After this, no woman would ever experience that with Michael.
A thought had been forming in my mind as I laid there next to Michael, in his arms, both of us strangely silent as we simply held each other. I cared about Michael, but that didn’t change the fact that he paid me for this. I knew that this literally made me a whore, but at the same time I couldn’t help feeling like I did something good. I had helped Michael in a way that wouldn’t have occurred to most people. Michael’s first time would never lead to feelings of regret or embarrassment. Not for either of us. This made me happy.
After our moment of shared quiet bliss, Michael looked at the clock and told me that his mom was going to be home in an hour. I asked him, “Are you feeling ready to have sex with me?”
Michael smiled anxiously and said, “Yes, definitely.”
As I began to kiss Michael again, I reached down towards Michael’s penis and felt that he was already fully erect again. I whispered to Michael, “Get on top of me.” As I rolled onto my back. I guided Michael so that he was positioned over me as I raised my legs up on either side of his body. I embraced him with my legs. I could already feel his penis pushing gently at my opening. I told Michael, “I want to feel you inside of me.”
As I felt Michael’s penis slide pleasantly into me the thought suddenly entered my mind. This is the moment that Michael is losing his virginity. This moment has been wonderful with everything that has happened between us so far, but it is right now that it is happening. And then my mind became once again lost in the moment. I wasn’t thinking about anything other than the way Michael’s penis felt as he pushed deep inside me. His rhythm felt wonderful. Because he came once already, I knew he would last longer this time. We were both caught up in the moment. So much so that I was oblivious to my own sighing. I was oblivious to the sound the bed was making. My only thought was how Michael’s body was making me feel, and how I was hoping mine was making him feel.
I was becoming unaware of the passing of time as Michael continued driving his penis into me. I knew we were running out of time, but I wasn’t thinking about it anymore. Suddenly, Michael’s body began to tense up. His rhythm changed and I felt his muscles tighten and his penis began to throb inside of me, and I knew. I pulled his body tight against my own as I felt his hot semen fill me in strong, warm pulses. Michael’s rhythm became a series of spasming thrusts as he finished cumming inside of me.
Michael rolled off of me with his sweet little grin as he looked at me. I don’t think either of us at this point want this to end but Michael reminded me that his mom would be home soon. I was hot and incredibly sweaty and so was Michael. My hair was a mess and worst of all, Michael’s semen was now oozing between my legs. I got dressed and discreetly fixed myself up the best I could, trying not to be too obvious as I wiped Michael’s semen up with my panties before putting them on. The unpleasant and cold feeling of wetness wasn’t nearly enough to cause me to regret anything that just happened.
Finally, both of us dressed. Michael escorted me back to the living room and towards the front door. I was about to leave when Jill suddenly walked into the room. I was concerned about her. She looked like she had been crying, and I was worried that she had heard everything. I was worried that she now disapproved of me, knowing that I was now a whore who had just fucked her brother and taken his money. But then she smiled as she rushed towards me. She wrapped her arms around me and told me she loved me. I hugged her back and told her I loved her and her brother and always would. And then she thanked me for helping Michael and then I knew. I knew that she knew what had happened. She knew, and yet she approved, and her tears were from joy, not sorrow.
As we said our final goodbyes and I began my awkward walk home, I began to have thoughts that had never occurred to me before. If I was a whore now, it isn’t anything like what I imaged it to be. I wasn’t damaged by it. I wasn’t suddenly feeling like I was evil or vile in any way. My feelings were actually contrary to that. I was satisfied with myself. I was actually proud that I did something with Michael that helped him. I helped him not just feel good physically for a moment, but also emotionally. I felt happy about it, I felt happy about every bit of it.
It wasn’t very late when I got home, and everyone was pretty much doing their own thing. No one was paying any particular attention to me as I got home. That’s not unusual but this time I was happy about my family’s general indifference towards me. I took a nice hot shower before getting ready for bed. It had been a long day and I was now exhausted and ready for sleep.
As I lay down in my bed, slowly drifting off to sleep, a debate started to take place in my mind. My whole life I had been taught that prostitution was evil and that whores were the worst people in the world. But now I was a whore, and I had just been paid for being a prostitute. I didn’t feel evil. I actually felt good about it. Then as I drifted off to sleep, I wondered. Would I ever do that again? I knew I would never take money from Michael again for sex. In fact, I was already considering giving him his money back, but would I take money from other people? I didn’t know.
The next day I went to school as normal. Nothing seemed different about me. I was the same person I was, though I began to think of Michael an entirely different way now. As I debated with myself about whether or not I was a whore now and how I felt about that I felt my phone vibrate. I glanced at the screen and saw that I got a message.
As I opened up the message, I saw that it said, “I heard you did great yesterday, good job.” Whoever sent the message wasn’t in my contacts so it didn’t say who it was from. I was nervous. Has Michael been talking about what happened and been giving out my contact information? Would he betray me like that? Nervously, I answered the text message, asking who this was. A moment later came the answer.
Suddenly I knew where Michael got a thousand dollars when I saw the message. I looked at the screen and read, “Oh hey, sorry, this is Bob, Michael’s dad. I was thinking of spending the weekend up at the lake. Are you available for the weekend? I could put money on your Cash App, just let me know.”
All of my questions were suddenly answered. I knew where Michael had gotten the money, and suddenly, I even knew more about myself.
I typed back, “Sure, 5K, bring condoms.” And now I knew. I am a whore. And I am not ashamed.
