I was extremely aroused and desperate to cum.
As much as I wanted Derrick to just fuck me right then and there on my desk, I couldn’t let him know that. It was part of the game we were playing. I still had to playact that I was reluctant and not wanting the boy sexually. So far our first successful roleplay was going well and I didn’t want to ruin it by begging my young lover to just take me. It was very difficult for me, however, and I was surprised it seemed easier for him.
This was not how our sex life was supposed to be, but ever since our trip to my beach house in Charleston, South Carolina on Folly Island it became this way. I was fifty-three and he was eighteen; he was the one that was supposed to be begging me for sex and the one who was supposed to not be able to keep his hands off of me. He was the one that should not be able to have such self-control over his sexual desires and needs, not me.
Every time I was alone with Derrick I wanted him. I wanted to kiss him, touch him, suck his cock, and have him fuck me. When I was not with him, I did not think about sex that often at all, but when I was with him it consumed my thoughts and desires.
That was not something new for me. I had always been a very sexual and sensual person and enjoyed sex a great deal, but now I was too old to have such lust for a man, well, young boy. Derrick had reawakened something in me that I thought was gone when my husband’s illness had gotten worse and my only desire then was to take care of him and prepare myself and my family for the eventuality of his death.
I didn’t give the boy my love, not true love; he would never have that. That was already given to my husband and no one would ever have that again. Yes, I cared for the boy. I had cared for him in one way or another since he first started helping my husband around the house. I then cared for him more when I saw close he and my husband became. Then even more as I watched how Derrick seemed to care for my husband when he was at his worst before cancer finally took the love of my life.
But caring for the young boy was not the same as the love I had for my husband. Derrick would never have that and he knew it; he didn’t even want that from me either. The boy cared about me the same way I cared about him.
What I did give Derrick was something he wanted and fantasized about. I gave him my body, my kisses, my touch, my mouth, and pussy to please him sexually. I gave him those things often and as much as he desired to have them.
At first, I told myself I was letting him fuck me so much because I knew he was an eighteen-year-old boy and eighteen-year-old boys are always horny. Let? I was not letting Derrick fuck me; I was giving it to him freely and often because I also desired him to fuck my brains out every chance we had. I wanted him just as much as he wanted me and I often was the one who initiated it. Not that he took much convincing. It was during our trip to my beach house in the early stages of our affair that I finally truly admitted that to myself.
Once I did admit my sexual desires for the boy to myself, he knew it and he took full advantage of it. Derrick knew I would not say no to him when he wanted to fuck me or wanted a blowjob or a quickie when we had time. I did not say no because I felt it was what he wanted; I did not say no because it was also what I wanted. Derrick figured out that I was not going to deny him sexual pleasure because I wanted it as desperately as he did, sometimes more than he did.
When this chapter of our story took place, Derrick was still in high school. He had friends he socialized with and went to parties with and that was great. I was glad he was doing that. He needed to do that. I was not going to begrudge him his youth. Plus, I had my family as well and regardless of how much I desired Derrick, my family came first and I would never place my sexual desires over them.
There were nights when Derrick would call me at one or two in the morning and be at a party and ask if he could come over. He did not need to tell me why; I knew why. I would be asleep and he would wake me up but I never told him no. Instead, I would get excited about him coming over, get out of bed, brush my teeth, and wait for him.
Sometimes I would put on makeup, even though it was not needed. Derrick had seen me without makeup many times by then. Sometimes I would put on heavier makeup if I had time and slip on one of the sexy lingerie outfits I purchased to wear for him.
He would come over and we would have some foreplay and fuck, or sometimes if he could not stay the night and wanted just a quickie I would give it to him. A few times all he wanted was a blowjob before he went home and I would be more than willing to give him just that.
Derrick sometimes did the same after an away baseball game; call me up and ask to come over and again I would never deny him.
When I had my granddaughters and when they spent the night, Derrick never came over and never asked to come over. I was not going to expose my granddaughters to him coming over even when they were asleep and Derrick respected that. Plus, I would have told him no. Again, they and the rest of my family are more important to me than he is and than anyone is and he also knows that.
Then we started discussing sexual fantasies, which I was more open to discussing and Derrick was more embarrassed to tell me his at first.
Even though I am on the submissive side when I am having sex, I am not a submissive. Enjoying for a man to be in charge sexually does not mean a woman is submissive in a relationship. While most of my fantasies seemed to be of me being submissive to Derrick and his eventually were him being dominant, he didn’t own me and I didn’t own him. Our roleplay was just that: roleplay and fun games and not the dynamics of our relationship.
Yes, I discovered some fetishes I thought I may have or at least explore, but that does not mean my young lover owns me in any way and I don’t own him. Derrick is free to do what he wants and yes, even date other girls his age if he desires, which I am sure he does. Just as I would be free to date other men if I wanted to, which I don’t. Jealousy is not an issue in our relationship.
It comes down to that while I care for the boy and his well-being and he cares for me and my well-being. While we talk and communicate and enjoy each other’s company a great deal, what he wants most from me is what is between my legs, and what I want most from him is what is between his legs.
When I first joined Lush I did so to read stories, just as I read some on other sites. I then decided to try and write one of my own and thought that writing about Derrick and me was a good way to start. I was very hesitant at first and had to ask Derrick if it was okay with him to make our sex life public on Lush in written words. He approved.
I thought, what harm could come out of the first two chapters at least, the first time we had sex? It was hurried and rushed and did not go into our sexual fantasies. As I wrote it and posted it and as people read it, I found myself enjoying writing it and people reading it and the feedback. I decided to continue.
However, what I write belongs to me and Derrick and not anyone else. I chose to share the things we did and I choose to omit other things we have done. Yes, I do plan on omitting certain things we have done I would prefer not to write about even though Derrick is trying to convince me to include them in a later chapter.
Outsiders looking in based on the things I have written message me and comment on my story and try to tell me what my feelings are and try and tell me the dynamics of my relationship with Derrick. Most are wrong but they keep trying anyway even though I have explained it several times in my story.
I was tempted to stop writing it and even take a break from Lush, but I am enjoying writing it. So I will continue and I will just ignore those outsiders who think they know more about a relationship they have no part in.
Before I continue I need to make one correction to the previous chapter. Derrick had untied my hands before he told me to stand up. I omitted that by mistake.
During our first successful roleplay session, where I was Derrick’s principal and he was blackmailing me for sex, my young lover told me to sit on the desk and masturbate for him.
I was sitting on the edge of my desk with my white blouse unbuttoned and my bra pulled up over my breasts. Derrick had already taken off my panties before he had spanked me with my sorority paddle. My tight, pencil skirt was pulled up above my waist to expose the thigh-high stockings, garters, and garter belt as well as my pussy. On my feet, I still wore my high heels. My hair was down and on my face were my reading glasses that the boy would not let me remove.
I had taken a break for a few seconds in our roleplay to make Derrick use the hand sanitizer on my desk. He had his finger up my butt and I wanted his hands sanitized. Yes, even after months into our affair I made him do that.
Derrick was sitting in the chair in front of the desk wearing his practice baseball uniform. He was grinning and waiting for me to start to play with my pussy.
Derrick had paddled me on two different occasions that day, each time giving me ten smacks on my naked butt. Five on one butt cheek and five on the other each time. He then finger fucked me with three fingers as I was bent over the desk, stimulating my G-spot, finger fucked my butt with one finger and had been pulling my hair. The boy had not made me orgasm yet and I wanted to – no, needed to – desperately.
“Spread your legs, Ms. Monroe,” Derrick ordered me. I did. “Wider, Ms. Monroe, I want to be able to get a good look at your pussy that Anthony tells me is so nice and fat.”
I blushed but did as he told me. Derrick laughed at me again.
“What?” the boy asked when he saw me blush. “You thought Anthony was not going to tell me, his best friend, how fat your pussy is? He tells me everything about you and what you have done for him and what he does to you.”
I blushed again and had a brief moment of panic. I know we were just acting out a game, but what if Derrick did tell his best friend, Anthony about us? The thought only lasted about a second and I calmed down. I trusted Derrick and when he said he would keep our relationship a secret I knew he would.
“But he promised,” I whined. “He promised not to tell anyone.” I was getting back into our roleplay. “And you promised you would not tell anyone.”
Derrick smiled at me. “Well, I guess Anthony lied, didn’t he?”
“Please don’t tell anyone, Derrick,” I begged. “Don’t show anyone the pictures.”
“That depends on you, Ms. Monroe,” he told me. “You do what I tell you to do and maybe I won’t. But then again, maybe I will. Honestly, it’s going to be hard to resist not bragging about having my hot old principal doing anything I tell her to do.”
“I will do what you tell me to do; I promise I will,” I begged. “Please don’t tell anyone or show them the pictures. I will make you feel good, I promise. I will make you feel really good. I’ll suck your cock and you can fuck me, and…and you can have me anytime you want. Just don’t tell people.”
“And what else, Ms. Monroe?” Derrick asked, not satisfied with my answer.
“I will…I will let you own me,” I promised my lover. “I will be your who… sex slave.”
I almost said whore but corrected myself. Derrick and I explored that verbal humiliation once. It was at the same time we explored him “forcing” me to suck his penis and him fucking my mouth. He called me a whore, slut, and bitch as he rammed his cock in my mouth, causing me to choke and gag. While I let him finish and he shot his cum all over my face, I didn’t enjoy either. I didn’t enjoy being called such names or the mouth fucking.
Derrick didn’t enjoy the verbal humiliation either. He felt very bad about it after and kept telling me he was sorry. I told the boy it was okay and that I wanted to try it. I told him I didn’t enjoy the “forced” blow job and he agreed, but I don’t think he was being honest with me. We never did those two things again, but him cumming all over my face we both liked and did that on occasion.
Derrick laughed. “See, that was not so hard, was it? Now let me see that fat, old pussy and start playing with it for me. Go slow, I want to enjoy this.”
I blushed again and nodded. I moved back more on the desk, placed my feet flat on the desk, and spread my legs for Derrick. Over the last few months since our affair began, I did start going to yoga classes again at a local gym. I did it for one reason only. I started again because I was tired of my muscles being sore and cramping up from the way Derrick would bend my body when he fucked me. Oh, I still got sore and achy but was beginning to also become more limber and flexible and able to position my body in ways I had not been able to do in a while.
“Damn, Ms. Monroe, you do have a sexy fat pussy and it’s so fucking wet,” Derrick commented after I exposed myself to him. “Your pussy is just glistening. I knew you were enjoying what I was doing to you. I know the type of woman you are.”
Derrick leaned forward to get a closer look at my pussy. “I like your tan lines,” he told me.
I almost said thank you but remembered I was playing a game and not supposed to be enjoying his compliments. The boy reached out and ran a finger up my pussy slit and I whimpered from pleasure.
“Your pussy is so sexy, Ms. Monroe. I do like a fat pussy and I like how darker it is than the rest of your body. Just slightly darker,” he told me and ran his finger up higher, “but right here, just where your clit is, it’s even darker. A dark little mound to protect your clit; that’s so sexy.” He then chuckled. “But won’t protect it from what I am going to do to it.”
Again I truly blushed. Even to this day, I had not gotten used to how Derrick would describe my pussy and the other private areas of my body to me or his vulgar comments about them. It still embarrassed me, but damned if it didn’t turn me on when he did. Even the times he would make his improper comments about my butthole aroused me. I also got sexually excited when I was giving him a blowjob and how he would tell me how good I was at it, even the times his words about it were crude.
The boy leaned back. “Now run your fingers over your pussy but don’t fuck yourself yet,” he ordered me.
I took my right hand and brought it to my pussy and started to run my fingers over my puffy vulva. Derrick was right; it was wet. Not just the inside of my pussy but my vulva was also slick with my sex fluid.
“Spread your pussy lips apart. I want to see the pink inside of your pussy,” the boy commanded me.
I used my thumb and fingers to spread myself open for my young lover. Yes, I was feeling humiliated and even degraded again even though I had done this for the boy many times. It did turn me on as it always did, however. Having Derrick tell me what to do excited me even more.
“Keep it spread for me and run your fingers up your slit, Ms. Monroe,” he told me.
I brought my other hand to my pussy and ran the fingers up and down the long slit of my pussy. I moaned from the pleasant feeling and then moaned louder when my finger brushed my swollen clit. I started to use my finger on my clit.
“No,” Derrick said. “Leave your clit alone for now, Ms. Monroe. You don’t get to cum until I allow it.”
I made a whimper of frustration but did as the boy told me. We had played around with orgasm denial before, normally when he tied me up. I loved and hated it. I loved how he would edge me and stop and edge me and stop repeatedly. I also hated it because I would be so desperate to orgasm that I would beg him to let me cum. Even though it turned me on, I didn’t like begging Derrick like that. It gave him all the control.
One night Derrick had me in tears, yes, actual tears, and begging him to let me cum. He had tied me up and was edging me constantly. When the boy would get to the point he needed sexual release, he would kneel next to my head and have me suck his cock until he orgasmed. He did that for a long time and I used my mouth to give him an orgasm three times. The third time, he pulled out of my mouth and ejaculated over my face, edged me once more, and then he did a cruel thing.
After he edged me and I was begging him to let me cum, Derrick laughed, got off the bed, put on his underwear and his shirt, and left the room. He left me tied up and went into the living room and watched the last few innings of an Atlanta Braves baseball game. I was pissed and frustrated.
After the game ended, the boy came back into the room, edged me again, and I started crying and begging him to fuck me and give me an orgasm. He had me suck his hard cock one more time, but didn’t cum. Instead, he untied me and told me I could fuck him now. I was so angry at him for what he did but I did get on top of him and fucked him anyway. My arousal and need to orgasm were stronger than my anger.
After, I was still mad, rolled over to my side and told him to go sleep on the couch or leave. Derrick snuggled up against me and spooned me and chuckled at my anger and frustration. Later I gave in to him again and we fucked one more time before we went to sleep even though I was still angry.
I was angry about it the entire next day. I was not angry at Derrick anymore but angry and even humiliated at myself for letting it happen and being turned on by it. I got my revenge a week later, however.
Derrick came over to spend the night again as we planned. When he came over I was wearing just my drill team uniform and nothing underneath. Of all the sexy lingerie I had purchased to wear for my lover, he liked seeing me in that uniform more. I even added a pair of fishnet thigh-high stockings to make it sexier.
When Derrick arrived I didn’t kiss him hello when he tried to kiss me and led him into the house. We sat on the sofa and when he tried to get me to sit next to him I told him I was not in the mood to fool around that night. I sat at one end of the sofa and Derrick at the other. I sat with my back on the armrest and my legs crossed under my butt, facing the boy.
I would spread my legs “innocently” and move my lower body to purposely wedge the crotch area of my uniform in my pussy so you could see the outline of it against the material. I would nonchalantly use my fingers to pull the wedge out and flash him my pussy. I did that several times as we watched the TV and other things to tease him.
Derrick kept glancing between my legs, adjusting his body because his cock was hard, and finally asked me to at least suck his cock if we were not going to have sex. I told him I was not in the mood.
He asked me a few more times as we watched the show and I kept teasing him and to his credit, he didn’t beg or get angry about being denied, but I could tell he was getting frustrated. I smiled at that. It was fun teasing him and I could understand why he got aroused when he denied me an orgasm.
After asking me for a blowjob several times, I finally made an exaggerated sigh as if I didn’t want to but agreed. I sucked his cock until he was about to cum and stopped and told him I didn’t want to do it anymore. About ten minutes later I did the same thing, then again, and then again.
Derrick knew what I was doing, but he also still got extremely frustrated and threatened to leave a few times and I would giggle and tell him to go ahead. I knew he was not going to leave and he didn’t and I was getting satisfaction from his tantrums from sexual frustration. I finally gave him a blowjob until he orgasmed in my mouth. When he did, the boy’s orgasm lasted longer than normal and he ejaculated so much cum that I could not keep all of it in my mouth when I swallowed it. His cum ran out of the corners of my mouth.
Derrick wanted to fuck me and I told him no. As we watched the series I kept teasing him and denying him sex. Even when we went to bed, I denied him sex and told him I was not in the mood. I would smile when he would try and I enjoyed his frustration and how the boy tossed and turned and could not sleep.
I wanted to have sex with him badly, but I can be a stubborn woman, and when I set my mind on something I don’t give in and I didn’t that night. If I don’t want to do something I don’t do it and if I want to do something I do it. I laughed when Derrick told me that he should just take what he wanted. I laughed because he was frustrated and also I knew he would never just “take it” if I did not allow him to.
The next morning I did allow Derrick to fuck me and it was great sex. After he orgasmed the first time he kept fucking me until he orgasmed again. Later he fucked me one more time before he went home. All three times my young lover fucked my brains out. It was well worth the denial I gave him and gave myself.
I never teased him like that again but that is another chapter. It sure was fun doing it that night and I wanted to do it again another night. I showed him two could play that game. Derrick still teases me and edges me at times though because he enjoys how I beg to cum and knows my love/hate relationship with it. When he finally does allow me to cum my orgasms are incredible.
So, since I am so stubborn at times and a strong-willed person you may ask why I was allowing Derrick to control me so much in our roleplay. It is because when we talked about how we would act out our games I promised him that I would do whatever he wanted of me. It was part of the game we both wanted to explore. The thought of stepping outside of the box of my normal personality and temporally surrendering to him in our roleplay excited me. I trusted the boy enough to make that promise and to surrender myself to him during our games.
Another thing about our roleplay when I surrender my control to Derrick is that I can only take it for the day or the night. After that, I have my need to reclaim my control and take back my life.
Now back to the roleplay, and I promise no more interruptions.
I ran my fingers up and down the slit of my pussy slowly and avoided touching my clit, just as Derrick told me to do. I kept looking at the boy’s face as he stared at my pussy. God, I wanted him inside me badly.
“Spread that fat old pussy apart for me, Ms. Monroe,” he told me. “Use both hands,”
I whimpered in embarrassment and frustration and even hesitated for a couple of seconds, but per our agreement when we discussed our roleplay, I did as he told me to do. I used both my hands and spread my pussy open for the boy.
“Fuck it’s so wet, Ms. Monroe, I can see it glistening from your pussy juice,” Derrick commented and I cringed at his use of words. I didn’t care for the vulgar term pussy juice. “Nice and pink on the inside,” Derrick continued as he stared at my open pussy. “Does it get this wet for Anthony?”
I didn’t know what to say. Should I say yes for the game or should I say no to stroke the boy’s ego?
“No,” I went with the latter.
Derrick laughed at me again. “Liar, I bet your pussy gets all wet and sticky when you sit around this office thinking about teenage cock,” he taunted me. “I bet Anthony is not the only student you are fucking. I bet boys line up outside your office and you make them fuck your old pussy one after the other to get out of detention.”
“No, I don’t!” I whined in protest.
Derrick grinned, still staring at my pussy. “Well, we should change that. Since you belong to me now, maybe I should spread the word around and show people the pictures of you and Anthony and pimp your old pussy out. I could earn enough money from your pussy and mouth that I would not have to get a summer job,” he taunted me. “You would have boys lining up outside your office then.” He then looked at my shocked face and laughed. “But I need to break you in first.”
“You…no, please, Derrick! Please, I don’t want that,” I begged. I was honestly confused again. Derrick never once said anything like that before, but I went along with it for the game. “I’ll do anything you want; please, just only you, okay, please.”
“Let’s just test that, shall we? Let’s just see if you are willing to do anything,” the boy said. “Start with fingering your pussy. One finger and fuck yourself slow.”
I nodded and moaned when I inserted my middle finger into my wet pussy. It slid in easily. I slid my finger in and out of my wet pussy slowly as Derrick gave me instructions on how to fuck myself. One finger became two and two fingers soon became three as I obeyed his orders. Occasionally he would tell me to lick my fingers clean and then fuck myself again.
As I fingered myself slowly, Derrick stood up and I watched as he pushed his baseball pants down to his knees and then his jock strap. The tan jock strap was still damp in the crotch area from his sweat from his baseball practice. Seeing my young lover’s erect eight-inch penis jutting out between his legs and his black pubic hair and seeing the glistening of his pre-cum on the tip caused me to start to finger myself slightly harder and faster.
My action didn’t go unnoticed by Derrick and he laughed. “Well, seems someone likes what they see. You like seeing my cock, Ms. Monroe?” the boy teased me and took his cock in his hand, and pointed it at me.
“Yes,” I replied honestly.
“It’s bigger than Anthony’s, isn’t it, Ms. Monroe?” he taunted.
“Oh, God, yes; so much bigger.”
“You want to suck it, don’t you, Ms. Monroe,” the boy continued his taunts.
“Yes,” I again answered honestly.
“I bet you want to suck two cocks, don’t you, Ms. Monroe. Maybe we should call Anthony to have him join us,” Derrick told me with a grin.
‘No, just yours, baby, please, just yours,” I pleaded.
I was still unsure if I liked that part of our game, Derrick teasing me about other men. While some of the erotic stories and books I have read included multiple-partner sex, I never fantasized about myself doing anything like that. I know I never would. It was just something I was not into at all. One sexual partner was plenty for me and I wasn’t the type of woman who did those things. I knew Derrick was not the type of boy who wanted that either. It was just part of our roleplay game.
“I think you are lying, Ms. Monroe,” he told me.
Derrick sat back down in the chair and started to slowly stroke his erection. I was hoping he would not cum that way because I did want it in my mouth and for him to cum in my mouth. As slow as he was stroking his cock, I doubted he would cum.
“Now lay down on your back and fuck your pussy, Ms. Monroe, and make yourself cum,” the boy ordered me. “Then I may let you suck my cock and taste my cum if you continue to behave.”
I nodded and had to push some objects around on my desk to clear a spot to lie down on. I then lay on my back on the hard desk, lifted my legs and spread them, and started to masturbate for the boy. I didn’t start slow; I had enough of going slow, being teased by Derrick, and teasing myself as I followed the boy’s instructions. I desperately wanted to orgasm and I knew just what to do to make myself cum quickly.
I inserted three fingers back into my pussy and brought my other hand up to between my legs and started fingering my clit. I adjusted the fingers inside me and found my G-spot and started to stimulate both areas of my pussy fast and furiously. As aroused as I was, I knew it would not take me long to orgasm.
“Finger your asshole, Ms. Monroe,” I heard Derrick tell me over my loud moans of pleasure and the wet, squishy sounds coming from between my legs.
By stimulating my G-spot, my pussy fluids became more abundant and also became thicker and a clear mucus-like fluid as it always did when I had my G-spot stimulated. I was very close to orgasm when Derrick told me to finger my butthole.
Due to being that close and without even thinking, I placed my feet flat on the desk and used the leverage to raise my butt. I then slid the fingers that were on my clit down and inserted a finger in my butthole. It slid in easily since my finger was lubricated by my slick, mucus-like sex fluid. I made a loud grunting moan of pleasure as my finger entered my tight hole. I did something I told Derrick I would never do when he asked me to do it in the past: finger fucked my ass.
Why did I do it then if I always refused to do it in the past? I can’t explain it. Maybe because I was so close to orgasm I didn’t want the boy to stop me from cumming. Maybe because I was so caught up in our roleplay game and had been obeying Derrick since we started and it was just out of how turned on I was by him “making me” do things to myself. Maybe it was a combination of everything. I don’t know why I did it, but I did.
“Deeper,” I heard my lover tell me, “and fuck your asshole.”
I grunted out again as I pushed my finger deeper into myself. Still stimulating my G-spot, I started to thrust my finger in and out of my butthole. I felt the very pleasant feeling of it, the same feeling I felt when Derrick did it to me. I even started to go faster.
“Uhhh…God…Uhhh, fuck…I’m going to cum,” I moaned out soon after I started fucking my butt with my finger. “Uhh, God, I’m cumming…uhhh God, I’m…!” I managed to call out one more time before I started making the high-pitched squealing noise I made when I had an orgasm.
As I orgasmed, I heard Derrick telling me to cum for him but his voice sounded like the TV or radio sounds when you are doing something else and not paying attention to it. It was like an ambient sound over the higher-pitched moans and whimpers I was making.
My body tightened and my toes curled under my feet like they were trying to grip the desktop. My face was contorted in a grimaced look of pleasure and I could feel my pussy and butthole constricting and releasing repeatedly around my fingers. I had an intense orgasm and the pleasure of it was increased by the finger in my butt.
After my orgasm ended, I pulled my finger out of my butthole but still kept the three fingers of my other hand in my pussy; they felt too good inside me to remove them. I lay on the desk panting and whimpering with my legs still spread, enjoying the afterglow of my orgasm.
I suddenly cried out again when I had an unexpected second orgasm and my pussy clenched around my fingers and my butt involuntarily thrust up off the desk. I was not expecting that! It was short but very intense. I heard Derrick chuckling after the orgasm ended. It amused him.
“Lick your fingers clean, Ms. Monroe,” I heard the boy tell me after the surprise orgasm ended.
Still in a euphoric state, I removed the fingers from my sex and looked down as I brought them to my mouth. My orgasm fluid and body’s natural lubricant were thick and clear as I raised my hand. My fingers and part of my hand were slick and glistening. As I raised my hand to my mouth, I saw a long strand of my sex fluid stretch from my pussy to my hand and it finally broke when my hand got to just above my stomach.
I touched my fingers to my lips, opened my mouth, and licked and sucked my fingers clean. I did so in a theatrical manner for Derrick’s benefit. I made exaggerated moaning sounds exaggerated sounds as I licked my fingers. It tasted good.
“Why, Ms. Monroe, you like the taste of pussy, don’t you?” the boy teased me. “Maybe tomorrow when I come to your office for our play time I will bring a girl with me or maybe Ms. Stewart and let her sit on your face while I fuck you. You can taste her pussy and lick her asshole.”
Ms. Stewart was a teacher at Derrick’s school that he has mentioned before and told me she was very attractive and all the boys fantasize about her.
I blushed at his comment and sat up on the desk. “Time out,” I told him.
Calling a time-out was a way to take a break from our roleplay. A way to stop it if something started to get out of hand or one of us was doing something the other did not like or want to do.
I called a time-out because I was embarrassed he mentioned about me and another woman having sex. Something I embarrassingly confided in him that I recently started to fantasize about. Not all the time and very rarely but it crossed my mind a few times. Derrick never teased me about it until that day and it embarrassed me.
I also called a time-out because I was ashamed of myself for using a finger in my butthole. Much more so than the other woman comment. The self-shame I felt made me a little angry at Derrick for telling me to do it and angrier at myself for doing it even though it gave me pleasure. The third reason I called a time-out was I needed to clean the finger that I had put in my butt.
I looked over the desk and saw a heavy paperweight and had a brief thought of throwing it at Derrick for making me use a finger in my butt. Yes, in my mind, I blamed him for it, not myself for doing it.
I reached over the desk and picked up the bottle of hand sanitizer instead. I pumped a lot of the sanitizing liquid on my hand, cleaned it and paid closer attention to my finger, and wiped it with a tissue. I did that three times before I felt my finger was clean enough.
Once I felt I was sanitized, I told the boy to continue. The break did nothing to diminish our desire to finish our game nor did my anger at him.
“Stand up, Ms. Monroe,” he told me.
“Why?” I whined. “I have done everything you asked of me. Can’t you just leave me alone now?”
Derrick chuckled. “Oh, so you cum and you think we are done? Ms. Monroe, we just started to play. Let’s call this your detention. No stand-up and turn around. Detention is not over.”
I did as he told me to. Derrick stood up and placed his hand on the back of my head and bent me over the desk again. He slid the hem of my dress up over my butt. I thought he was going to fuck me. I was hoping he was going to fuck me.
Derrick leaned his body over mine and I felt his hard penis press into my butt crack. I flinched involuntarily when it touched my butthole. I knew it was an accident and he was not going to put it inside me there. He adjusted his body when I flinched and chuckled at me and his penis slid up the crease of my butt again. The boy then ran his fingers up and down my pussy slit once more and I moaned out in pleasure.
“You are so wet, Ms. Monroe,” he told me and roughly shoved three fingers into me at once. They went in easily and I made a loud gasping moan of pleasure. “I bet I could put my entire fist inside your pussy right now.”
My head jerked up. “Don’t…don’t you dare!” I cried out and he laughed at me.
“Oh, don’t worry, I won’t. The next thing that goes in your old pussy is my cock,” he assured me. “You want to fuck you now, don’t you, Ms. Monroe?”
“Yes,” I replied, my voice husky sounding from desire.
“I have to admit I want to fuck you just as bad,” he told me and then pushed his fingers into me deeper, and again I gasped out. “But I am having too much fun with you right now.”
I was getting angry again. Angry and frustrated because, damn it, I wanted to get fucked! The orgasms I had helped my sexual frustration only a little. I wanted to feel my young lover’s teenage cock in my pussy.
Derrick pulled my arms behind my back, picked up the soft cord, and tied my hands behind my back again. I struggled and whined and this time was not play-acting, but he was too strong. The boy then picked up the paddle once more.
“What…no…please, baby, I…what did I do wrong?” my voice was loud and whiney and pleading.
I didn’t want to be paddled again! I could have stopped it by calling time out, but I didn’t. Even though I didn’t want to be paddled and I knew it would hurt, my newly discovered spanking fetish won out and I didn’t stop the boy.
“You started to get belligerent with me. Isn’t that what you told me I was, a belligerent young man?” Derrick told me. “You said I should be paddled for it so I guess you should be as well.”
“When did I do that? I am sorry…I didn’t mean it,” I begged. My begging was partly game and partly real.
“When you asked me to leave,” my lover answered. “You wanted me to leave after you got off and had no concern for my needs. That is not what a woman does to a person who owns her pussy as I own yours. You should be on your knees begging me to allow you to please me.”
“Yeah, like that is going to happen,” I replied in a snarky tone. That was not play-acting. I was not going to get on my knees and beg for his cock.
I cried out when the first smack of the paddle suddenly hit my butt cheek and again at the second and third. Derrick switched to my other butt cheek and paddled it three times. He gave me another smack with the paddle on the other butt cheek again.
“Okay, okay…please stop!” I cried out as tears ran down my face. I was not sobbing or crying, but I had tears. “I’ll do it. I’ll beg for it, please don’t paddle me anymore.” My ass felt like it was on fire.
Derrick did stop and put the paddle back on the desk. “I didn’t paddle you to make you beg for my cock, Ms. Monroe. I paddled you to punish you. You will beg for my cock because you want it, not because I made you.”
Derrick started removing his clothes. He kicked off his shoes and then pulled his jock strap and baseball pants off that he had pulled down to his knees. He then sat back in the chair.
“Stand up, turn around, and get on your knees,” he told me. I did as he told me and kneeled between his legs with my hands tied behind my back. “Closer,” he ordered me.
I moved closer until his erect penis was about an inch from my face. I could smell his crotch from being the short distance to it. It was spring and had been hot and humid that day and apparently, Derrick had worked up quite a sweat during baseball practice.
Derrick placed a hand on the back of my head and his other hand gripped his cock at the bottom of his shaft. He pushed my head down and I opened my mouth to take his cock inside it. When I tried to move my head down more so his penis would go in my mouth, Derrick stopped me by pulling my hair.
“Wow, so eager, Ms. Monroe, but not yet; you need to beg me to let you suck my cock,” he taunted me.
I looked up at Derrick and closed my mouth and shook my head. Derrick grinned and pointed his penis at my face, pushed my head lower, and then ran the tip of his cock over my closed lips. His precum spread on my lips like lip gloss. I opened my mouth to give him a blowjob but he pulled my head away.
“I’m not begging to suck it,” I told him defiantly. “You want to cum worse than I want to suck it,” I said with confidence.
“Yeah, but I don’t need you to suck my cock to cum,” Derrick replied.
Derrick then proceeded to masturbate. He held my head in place by my hair with one hand and jerked his penis with his other. I watched, turned on by seeing him masturbate and by everything else we had done up until that point, and yes, I wanted him in my mouth but I was not going to beg!
My young lover must have been as aroused as I was or even more because it didn’t take him long to orgasm.
“Ugh, fuck, I’m going cum,” the boy grunted out. “I’m going to paint your face with cum, Ms. Monroe.”
I was glad I was wearing my glasses. I was going to be able to see him ejaculate. I liked watching him cum. I had learned the hard way to close my eyes when the boy ejaculated on my face. One night he did it to me and when his cock exploded a huge shot of it landed right in my eye and it burned. The glasses would prevent that.
Derrick was just as aroused as I had thought. His cum was thick, warm, and gooey and I watched as it splattered all over my face, my glasses, my lips, and my hair. There was a great deal of it. The boy kept grunting and ejaculating and I thought he would never stop. Yes, that was an exaggeration but that was how much he came and how long his orgasm lasted. As his fluid landed on my face, I had instant regret I did not beg him to let me suck his cock. As much as the boy ejaculated I wished it had been in my mouth. I was able to lick around my mouth to taste the cum that landed close enough.
After Derrick’s orgasm ended, he pushed my head down to his penis. Without being told, I parted my lips and took his cock into my mouth. I sucked and ran my tongue over the head and swallowed what fluid I could coax from his cock until he pulled my head off of him.
“Stay right there,” the boy told me and stood up. I closed my eyes because cum was running down my forehead to my eyes.
I heard the boy doing something on the desk and then felt him remove my glasses and he wiped around my eyes with a tissue. It took four tissues for him to clean around my eyes before I could open them. Derrick didn’t clean the rest of my face, just around my eyes. I opened my eyes and looked up and saw my lover standing over me and pointing his phone at my face.
“No, don’t, please…please, Derrick, no photos, please,” I begged.
This was part of the game. I knew he would not take any pictures of me like that or any risqué or nude pictures of me or videos of us having sex. We never even talked about it because we both knew we didn’t need to and we both knew neither one of us would allow it.
Derrick laughed at me. “But you look so sexy with my cum all over your face,” he told me. “Plus I need some type of proof that I am fucking you for the blackmail.” Derrick pretended to take a photo.
The boy put his phone in his duffel bag and started to get dressed. He started to get dressed! I was stunned and just watched him.
“What….where…you are leaving?” I asked when the shock of him putting his clothes on wore off.
“Yes, I got what I needed, Ms. Monroe,” he told me with a chuckle. “You don’t think I came in here just to fuck you? Don’t flatter yourself. Why would I want an old worn out pussy like yours when I have young girls my age with tight pussies I can fuck? All I needed was for you to change my grades, put me back on the team, and get my scholarship back. Everything else was just a bonus and since you don’t want me to fuck you, I won’t.”
I was still dumbfounded and very sexually frustrated as I knelt on the floor, my hands tied behind my back, and my lover’s cum running down my face. There was no way he was really going to leave me! I knew he still wanted to fuck me because his penis was still erect. He was not going to leave, right?
I watched as Derrick finished dressing, picked up his sports bag, and walked to the door. Without even looking back at me, the boy unlocked the door and opened it.
“Wait!” I cried out. “I will! Please don’t leave…I…I want you to fuck me, please, Derrick, please don’t leave and please fuck me!” I begged the boy.
Yes, I begged him and gave him what he wanted and my pleading was not part of the game. I needed him inside me so badly that I begged.
Derrick turned his head and had a huge grin on his face, a grin of triumph. He had defeated me and he knew it.
“You will do whatever I tell you?” he asked.
“Yes, I promise I will,” I whined my reply without hesitation.
“Stand up and bend back over the desk,” he ordered me.
As Derrick put down his bag and started to get undressed again, I struggled to get off my knees. It was hard with my hands tied behind my back. I was still trying to stand by the time my lover was undressed and he had to help me up. Once on my feet I turned and bent over the desk.
Derrick came behind me, nudged my legs for me to spread them further apart, and then ran his hard cock up my pussy slit.
“This is what you want?” the boy teased me.
“Yes, please. Please, baby, fuck me now,” I begged.
Without another word, Derrick pushed his cock into my pussy in a single hard thrust and I gave a single, loud, drawn-out cry of pleasure. My pussy was so wet, Derrick entered me easily. Derrick reached around and grabbed my breasts and squeezed them hard as he pinched my nipples. It hurt but I didn’t care.
My young lover thrust hard into my pussy three or four times or maybe five; I can’t remember. He then pulled out of me as he kept mashing my breasts and pinching my nipples painfully hard.
“No, please, baby, please put it back in,” I begged.
“Tell me what you want, Ms. Monroe,” the boy said.
“I want you to fuck me, please. Please, baby, I want to feel you cum in my pussy. Please fuck me hard, Derrick. Wear my old pussy out, please,” I replied. “It’s your pussy, baby, you own it.”
Derrick chuckled once again and thrust back into me hard. Derrick pushed my head to the desk and started fucking me so hard the desk started creaking and shaking and the lamp on the desk fell over. As he fucked me, the boy brought a hand to my face and started smearing the cum over my face and then placed three fingers on my lips. I opened my mouth and started sucking them. The fluid was now chilled but I didn’t care; it still tasted good. Derrick pushed his cock deep into my pussy and I made a muffled moan and he stopped thrusting into me.
“You like that, don’t you, Ms. Monroe? Sucking my fingers like a cock while I fuck your pussy?” the boy taunted me.
“Umph, es…es, aby,” I told him as he made me continue to suck his fingers.
“I bet you wished it was a cock, don’t you? I bet you wished it was your other young lover, Anthony’s cock in your mouth as I fuck your pussy, don’t you? You, taking two eighteen-year-old cocks. One cock in your old pussy and one cock in your old mouth.”
“Ooo, Ith, on’t!” I tried to tell him, no, I don’t, but he was still making me suck his fingers.
“Liar,” Derrick told me and laughed. “Yes you do, you like young cock too much not to want it. Now suck my fingers like you would suck Anthony’s cock while I fuck you.”
I didn’t reply and he didn’t expect one. After his comment, the boy started to fuck me hard again as I sucked his fingers like a cock.
As I mentioned previously, I never had even considered or thought about or even fantasized about multiple partners. Naturally when I was married, other men sexually never crossed my mind. Now, however, Derrick put that thought in my head. Damn him! I still didn’t want to do it and I was not going to do it, but as Derrick fucked me and made me suck his fingers like another teenage boy’s cock the thought came unwanted to my mind.
I thought about his friend Anthony in front of me with his cock in my mouth while Derrick fucked me from behind. I never met Anthony of course but had seen photos of him on Derrick’s phone so I knew what he looked like. I didn’t like thinking of it, but could not help it.
I do want to clarify, I did not have that fantasy about being fucked by two boys and after that day I still never had that fantasy.
As Derrick pounded my pussy with his cock and as I sucked his fingers, I had another orgasm. After I came, the boy removed his fingers from my mouth and kept fucking me. He suddenly stopped fucking me, removed his fingers from my mouth, and pulled out of me again.
“Don’t worry, I am not done with that pussy yet,” he assured me before I could beg him to keep fucking me.
I looked over my shoulder and saw him pick something off the floor and he got behind me again and grabbed my hips and entered my pussy once more. The boy then bought his hand to my face and put his jock strap to my nose.
“I know how much you like smelling stinking and skanking cock, Ms. Monroe,” he told me. “Take some good deep breaths.”
I did. I would have without being told to. The pungent, musky smell was wonderful to me and I inhaled several times before Derrick pulled the jock strap away. I even whimpered in disappointment when he did so. I wanted to smell it more.
Derrick then put the smelly jock strap over my head and adjusted it so the crotch area would be pressed to my nose and mouth.
“Open up,” he told me.
I opened my mouth and the boy stuffed the crotch portion of the jock strap in my mouth and gagged me. I could taste it, actually taste what I had smelled. I loved it! Again the boy started fucking me.
I soon felt him spread my butt apart, felt his spit dribble on my butthole, and closed my eyes knowing what he was about to do. When Derrick put his finger in my butt and pushed it in deep, I had another orgasm as soon as his finger was in my ass as far as it could go.
Derrick fucked me and finger fucked my asshole until he also had an orgasm and ejaculated into my pussy. After he was finished, he removed his finger from my butthole and collapsed on top of me.
“Fuck, Ms. Monroe, I have to admit, your old pussy is fantastic,” he told me. “I am going to have to get some more of that later.”
Derrick stood up and untied my hands, cleaned his hands with the sanitizer without being told, and started to get dressed. I stood up, removed the jockstrap from my head, brought it to my nose, and smelled it one more time before I handed it back to Derrick. I adjusted my clothes as he put the jock strap in his bag.
“I am coming over to your house tonight, Ms. Monroe,” he told me. “I am going to get some more of that pussy. I want you to wear something sexy for me.”
I leaned back on the desk and just nodded. Apparently, our roleplay was not over. We did take a break from it, however.
I cleaned up myself and changed clothes and put on fresh makeup while Derrick took a shower. While he was in the shower I fixed him something to eat. I knew he had to be hungry since he had come over right after practice. I ate a little also.
After we ate, we sat on the sofa, and cuddled as we talked about our roleplay, what we liked and didn’t like. There was nothing I didn’t enjoy, yes, even the paddling, and nothing he didn’t enjoy. After a while, we started making out for a while until Derrick told me that it was time for Ms. Monroe to get ready for her company.
I went into my bedroom and changed into some sexy lingerie and awaited my young lover who was blackmailing me for sex.
We continued our roleplay game. Derrick started by pretending to take photos of me in erotic poses and then nude vulgar poses as I protested and then we started the sex. Derrick tied Ms. Monroe up, teased her with orgasm denial, forced her to suck his cock and swallow his cum, licked and fingered her butthole, and fucked Ms. Monroe’s brains out that night. Ms. Monroe was well satisfied that night and going to be much nicer to her student Derrick in the future.
I later asked Derrick if he really would have left the office if I did not beg him to fuck me. He laughed and told me no and that he was so damn horny even after cumming that he would have begged me for pussy. I slapped him playfully on the chest twice, one time for being vulgar and another time for tricking me.
