After Derrick left that Sunday morning I did take a nice warm bubble bath to soak my sore body. It helped a little, but I was sore almost all over the rest of the day.
I did not see Derrick for the next two weeks and as I mentioned we did not have sex again for a little over three weeks. He started back to school after his Spring Break ended and started baseball practice the same week. I had family things to do and he had his friends he spent time with. Then the week after my granddaughters had their Spring Break and I took them and their mother and my son-in-law on a Disney Cruise.
I didn’t pine or sit and mope thinking of Derrick. My relationship with him was not like that and my family always came first for me. Yes, I sometimes thought about the sex we had, but I also knew that we would have more sex in the future and I could wait. As for Derrick, I was sure he was not waiting for me and was most likely going out with girls his age. I didn’t have a problem with that. I thought he should be dating girls his age. The thought of him having sex with them did not make me jealous. He always came back to me.
The week after I got back from the cruise I came down with a case of pancreatitis and spent four nights in the hospital while they treated it and he did come and see me once. I told him not to come to see me anymore because I was also being visited by my oldest daughter every day and didn’t want her to see him there. My youngest was at college but she called every day to see how I was. I was drugged up on strong painkillers for most of my stay, so I didn’t remember much of when people came to visit.
After I got out of the hospital, I was still not at my best and not in the mood for sex until I felt better. When I did feel better I decided to take Derrick on a weekend trip. Our first of many we had. I took him with me to my beach house on Folly Island in Charleston, SC.
My husband and I had purchased the beach house seventeen years ago and we got a lot of use out of it and so did my kids. We never rented it out and we had a man who lived in the area who was a caretaker for the house when it was vacant. Now that it was getting close to summertime, I wanted to go check on it and spend a few days at the beach. Also, my youngest daughter had just gone there for her Spring Break from college and took some friends so I wanted to make sure it was still standing.
I won’t go into a lot of detail about the trip or the sex we had. That would be rather redundant to write and read about. We did have a lot of sex though and I often initiated it by seductively enticing him to simply just “jumping” the boy and telling him to fuck me. The sex varied from intimate and passionate and love-making type sex to either me getting on top of him and riding his cock hard to Derrick fucking my brains out like he did that first night we spent together.
My desire to have the boy surprised me in the early days of our affair. I will try and explain what I mean by that. I had gone many years without sex and as I mentioned before I was okay with not having a sex life. After Derrick and I started our affair and we were not together, I didn’t sit around thinking about him all the time or desperately feel a need to have him. However, when we were together I would get immensely horny and did have a strong lust and need for Derrick sexually.
I had and still have a strong desire to kiss him, touch him, have him touch me, to have his cock in my mouth, and for him to fuck me. I have a hard time keeping my hands off of his young body. Luckily he feels the same. One example of how much I desired the boy was on our first trip to my beach house.
We left on a Friday after Derrick got out of school and he had a baseball game right after so we didn’t leave until a little after seven in the evening. We had not had sex since that first night he spent with me so while I didn’t know about Derrick, I knew I had not had sex in one day shy of three weeks. I was looking forward to our time away at the beach house with the boy.
I thought how nice it would be that we would not have to sneak around and how we could go out in public together as lovers and since the weather was going to be nice, we would be able to go to the beach. While I knew we were going to have sex that was not the first thing on my mind. That was until Derick showed up at my house for us to leave.
He parked his truck in my garage and was still wearing his baseball uniform. I wanted him right then! I wanted to get on my knees and suck his cock and smell his body after he had been sweating from the humidity. That surprised me. It surprised me because I had not been thinking of having sex with him until he arrived. When I did see him that was all I could think about!
I did have self-control, however, and refrained even after a passionate kiss hello. We had to get on the road since we were leaving late. Derrick wanted to take a shower but I told him we didn’t have time so he just changed his clothes. That was only part of why I told him not to shower. I wanted to smell his scent when we got to the beach house and have him fuck me before he showered.
I could have initiated sex with Derrick before we left, a nice hard quickie would have been great. I didn’t, however, because we were new to our affair and I didn’t want to appear desperate. I thought if I appeared desperate it would give Derrick the upper hand and I didn’t want him to have that. After that weekend, though, the boy knew he had the upper hand when it came to sex in our relationship.
We took my car. Derrick has an older model pickup and I drive a late model Lincoln Navigator so yes we took my car. I did want him to drive through. I am old-fashioned I guess because I think men should always drive.
The drive to Charleston is about four and a half hours. The route is taking Interstate 16 to Savannah and then getting on Interstate 95 for about another hour and then you get off the interstate and travel a state highway into Charleston. That would be the normal route most people take. However, I don’t go that way. Once we got off Interstate 95 I like driving the back county roads. I like taking them because they go through the marshlands of the Low Country and it’s a more scenic route. That route only took about forty-five minutes longer, so not bad at all.
On the drive, we talked about his game, how I was feeling after my pancreatitis, how his school was going, what plans he had after he graduated, and me telling him how much he will love Charleston. I was surprised Derrick didn’t mention anything about sex; some type of crude comment to make me blush and embarrass me.
Me? I was thinking about sex constantly and wanted Derrick so badly. All I could think about was what we were going to do when we got to the beach house. Kissing him, him touching my breasts, sucking his large cock, and Derrick fucking me consumed my thoughts. By the time we pulled off Interstate 95, I was extremely horny and I could feel the dampness in my panties between my legs.
“Pull over at the next off-road,” I suddenly blurted out.
It was dark and we were about an hour from Charleston on a back road that was deserted. We had not seen another car for about the past thirty minutes.
“Why?” he asked with concern in his voice. “Are you feeling sick?” He may have assumed since I just recovered from pancreatitis I was feeling ill.
“No,” I assured the boy and smiled at him seductively. “I’m horny and I want you to fuck me right now.”
Derrick didn’t ask any further questions and pulled off onto a dirt road that looked like a hunter’s road or fishing trail-type road. He drove down the road about a hundred yards until it became blocked by a chain across the road. As he was driving down the road I was already pulling down my shorts. Derrick stopped the car as I was untangling my shorts from my sneakers.
“Let down the back seats and there is a blanket in the back you can lay down,” I told him.
Derrick didn’t ask any questions but just smiled and got out of the car. He laid down the back seats and placed a blanket down as I pulled down my panties and then crawled into the back of my car; me still wearing my tee shirt, bra, and sneakers. Derrick got in and shut the door and got on top of me as I spread my legs for him. We started kissing as I reached under the boy and started unbuttoning his shorts and pulling them down. Derrick helped me with his underwear and both his shorts and underwear until they were down to just above his knees.
We didn’t waste time with foreplay, it was not needed. I was very wet already and his cock was hard. I cried out when Derrick entered me in one, hard thrust and gripped his shoulders tight as he started fucking me in the car. I had not had sex in a car since I was nineteen and I found it exciting. The Navigator was much larger than the last car I had sex in and did make it much more comfortable.
“Harder, baby, fuck me harder!” I cried out.
“I want to enjoy your pussy,” Derrick told me as he fucked me slowly. “It’s been a while since I had it and I want to enjoy it.”
I thrust hard up into the boy, “You can enjoy my pussy as much as you want later and all weekend, just fuck me hard right now,” I told him in a commanding voice.
Derrick did. He fucked me hard and I orgasmed rather quickly and he did soon after. I felt satisfied for the moment. After our quickie, we got dressed and continued our drive to Folly Island.
When we go the beach house, Derrick carried our luggage into the home and I showed him what bedroom to put them in. As soon as he put the last suitcase on the floor I got on my knees and started to give him a blow job. He didn’t protest at all.
After he sprayed his cum in my mouth, Derrick had me take off my clothes, get on the bed, and masturbate for him and I did so eagerly. My lover wanted me to finger my butthole, but I refused to do that. I did pull my fingers out of my pussy and licked my fluids and his cum off of them several times before I brought myself to orgasm. After, he fucked me again and then we unpacked and I gave him a tour of the house.
I enjoyed the trip and so did Derrick and from more than just sex. We got to go out in public and be lovers and not have to hide our affair. We got to show public displays of affection, but not obscenely so; just held hands, light kisses on the cheek or lips, and walked with my arm looped through his as I showed him the beauty of Charleston. We did get some odd looks due to the age difference, but we didn’t care.
The weather turned out to be nicer than the predicted forecast so we got to go to the beach in our swimsuits. Derrick liked me in my two-piece bathing suit and liked putting the sun lotion on me. A few times I had to slap his hands away when they got too close to my private areas. We were in public. He also immensely enjoyed fucking me when we got back to the house when I smelled of the coconut-scented lotion.
After we got back home, Derrick and I had sex one more time and I sent him home. I decided to unpack and wash my clothes. I noticed that the boy had left the practice baseball uniform he was wearing before the trip. I decided to be nice and wash it for him.
Before I put his shirt in the wash I smelled it and then also smelled his jock strap. I suddenly wished I had not sent him home so early.
When we got back home our relationship status had been firmly sealed into a full-blown affair and I started being much more relaxed and open with Derrick. I also wanted to make things sexier in our affair. I did that by purchasing sexy lingerie outfits for me to wear for him and more sexy panties and bras for me to wear for him. He especially liked the garter belt and thigh-high stocking lingerie outfits I bought. I even wore my drill team uniform for him again on occasion. He liked that a great deal.
I also felt comfortable discussing fantasies with Derrick, fantasies I never acted out on but have had for a long time, and even fantasies I never discussed with my husband. I think I need to explain how I got these fantasies and why I never acted them out with a man I was married to for twenty-plus years and was completely in love with.
I mentioned before that I am a fan of erotic fiction and have been since I was a teenager. I started reading trashy romance novels like the Harlequin romance books. After reading those books I had it in my head that when I lost my virginity it would be like in one of those books. I would lose my virginity romantically and it would be wonderful. It would be in a barn after being caught in a rainstorm and I and my lover would be all soaking wet or in a large canopy bed in a romantic setting. Well, that didn’t happen. I lost my virginity at age seventeen in the back seat of a Ford Bronco that my boyfriend drove.
Was it wonderful? It was over quickly but I did enjoy it a great deal and did have an orgasm. I enjoyed it so much that right after I asked when we could do it again. We did it again and I had another orgasm. I discovered that night I was going to really like sex.
One day when I was sixteen, I picked up a copy of the first book in the Sleeping Beauty series at a bookstore in the mall. It was written by Anne Rice under the pseudonym of A. N. Roquelaure. I had read her vampire books and enjoyed them and thought her erotic book would be good. It was a lot different than I thought it would be but I enjoyed it so much that I read the other books in the series. The first book made me masturbate for the first time while reading some of the passages.
I won’t go into detail about the books, but anyone who reads them will understand when I say they are full of sexual things I would never do at all. They are full of hardcore bondage and sadism and masochism, multiple partner sex, gang bangs, humiliation, lots of anal stuff, and other things. While I would never do those things and even though some of the passages were disgusting, I could not deny a lot of it what I read aroused me. I discovered you can be aroused by something you would never do sexually, but thinking about it was ok.
There were some things in the books that I did think would be fun to try just for sexual pleasure; bondage, surrendering that much control to a man sexually, and even the spankings; yes spankings! But I never did any of that. I then progressed to much dirtier erotica like Penthouse Forums and other erotic books.
With my first boyfriend, I was too young, too scared, and too innocent to bring it up. When I started dating my husband I was again too young, too scared, and too innocent to bring it up. After my husband and I were married I didn’t want to do those things with him and of course, never thought about or was even tempted to cheat on my husband.
I didn’t want to bring up my fantasies with my husband because I loved him too much, not that I did not trust him. He was the love of my life and then the father of my children so the mere idea of him and I doing those things did not sit well with me at all. Then I started my affair with Derrick.
With Derrick, I saw my chance to at least talk about those fantasies with him even if I was too afraid to act out on them. So I eventually did and eventually got out of him the sexual fantasies he had about me. The thought of him masturbating about me even before we had sex for the first time aroused me.
Derrick’s were rather simple. He fantasized about me being in some type of position of authority over him and him seducing me or blackmailing me to have sex or me seducing him. Me being his teacher or me being his school’s principal was his “go-to” masturbation fantasy he told me.
Mine were more kinky and taboo. Now what I considered taboo many people won’t think that there are too kinky at all, but to me they are. It was not some type of Master/slave BDSM stuff. I am not into that nor am I into the verbal humiliation of being called a whore or slut or bitch and won’t tolerate anyone who calls me such. Calling a man Master did not sit well with me either and did not turn me on.
What I did fantasize about was giving up complete control of myself sexually to someone I knew I could trust, bondage, and maybe even try a spanking. Derrick was someone I could trust 100% and I knew he would not take advantage of the situation. A sex slave for the night for just fooling around but without all the Master/slave stuff that I was not into.
It would be easy for me to surrender myself sexually to Derrick, I about did that anyway and rarely turned him down when he wanted sex. Some of the other things may be more difficult for me because I am not a submissive person non-sexually.
So how it all started was we talked about such things. As I mentioned I am a planner type person and have a need to plan things out; so even with this, I wanted to plan things out. We decided, well I decided mostly and Derrick just went along with it, was to roleplay our fantasies into some type of roleplay scenario. I thought that might be fun and I read erotic stories people did that and enjoyed it so decided to try.
We sucked at it! Derrick and I are not academy award-winning actors; I doubt we could even land a role in a local theater play. We tried it several times, could not help but laugh at ourselves and our lack of improvisation skills, and just ended up having sex.
Derrick even tried spanking me, with my consent. He placed me over his knee, I pretended to struggle, and he pulled down my panties, and smacked me a few times with his hand. He did not do it hard and while it stung slightly it was not painful at all and I giggled the entire time. He told me he could do it harder because he did not want to hurt me. I lied and told him I didn’t want him to hurt me either. Truth was, I enjoyed the playful spanking and wished he would have done it harder.
I think I discovered I had another fetish; a being spanked fetish. I was not sure, however, since he never spanked me again and I never asked or implied for him too. I was not going to do something he was uncomfortable with and he was not going to do something I was uncomfortable with.
We tried bondage, him tying me up to the bed using some pantyhose I had or some of my scarves. We both liked that.
We just could not get our roleplay right. We stuck with it, however, and finally got it right one evening. We decided to combine both our fantasies together. We acted out this particular scenario one hot and humid Friday early evening after one of his baseball practices.
Before I go into the details of that roleplay scene I want to stress that everything was consensual. When I begged and pleaded for Derrick not to do things to me or told him no, it was all part of the roleplay. I cannot stress that enough and will remind readers of that as I tell that part of our story.
A couple of other things before I write about our roleplay scenario that one Saturday evening; this in no way is a reflection of our normal relationship. Also, we don’t roleplay our fantasies often. As I write this chapter, Derrick and I have been involved sexually for just about a week over a year. If you average out the times we roleplayed our taboo fantasies with each other it would not even equal once a month.
While we both enjoyed and considered the roleplay fun and exciting, we both just preferred “normal” sex.
I was sitting behind the desk in what used to be the home office but it does not get much use anymore since my husband passed away and I am retired. I was dressed in one of the older business suits I used to wear. I was wearing a navy blue jacket over a white blouse and under my white blouse I was wearing a lacy black bra. The bra was sheer and between the lace patterns, you could see my breasts and brown nipples. I purposely wore the black bra with the white blouse so it could be seen under my top.
I was wearing a tight navy blue pencil skirt that came just below my knees and was wearing black thigh highs held up by garters that were attached to a garter belt around my waist. The garters and garter belt were part of a lingerie set I had purchased. I was wearing black lacey panties that matched the bra and wore them over the garters. When I wore my thigh highs and garters and garter belt, Derrick liked for me to keep them on when he fucked me. I, therefore, put my panties over them so he could take them off and I would still be wearing the rest.
I had my hair styled professionally and piled up on top of my head but with locks coming down to frame my face. On my feet were high heels I have not worn in years. I was wearing my reading glasses. They are hipster-type, black-framed glasses.
I was pretending to read some papers on my desk when there was a knock on the door to the office.
“Come in,” I said.
Derrick walked in and he was wearing his baseball practice uniform but did not have his cleats on and was wearing just sneakers. He was carrying his sports bag.
“You wanted to see me, Ms. Monroe,” he asked. Just some information, Monroe is not my real last name and Stephens is not Derrick’s.
I looked up and frowned, “Please remove your cap, Mr. Stephens,” I told him in a curt tone. “It’s just common courtesy for a man to remove your hat indoors.”
Derrick rolled his eyes but took off his ball cap. “Have a seat please,” I told him. Derrick sat down in the chair I had placed on the other side of the desk. “I suspect you know why you are here?”
“If this is about my grades you can save me the lecture,” he told me in an arrogant and disrespectful tone to his voice. “Coach already told me I need to work on them.”
“That is just one of the reasons I called you into my office,” I said and looked at the boy. “Your grades are an easy fix. You are off the team until you improve them.”
“That’s bullshit!” the boy said loudly. “How the fuck can I pull my grades up to play baseball with only one semester left in the school year. I graduate this year and if you kick me off the team I will lose my scholarship.”
“Don’t you dare use that language with me, young man.,” I told him sharply. “You just bought yourself a week of detention to go along with the other week I was going to give you for your recent behavior and disrespect you are showing your teachers.” I gave Derrick a cruel smile as if I was enjoying punishing him.
I then smirked at him and gave him my “bitch look”. Yes, I did have that type of look. When I worked I was in upper management at a regional office for one of the largest property and casualty insurance companies in the U.S. I was very good at my job and well respected and I had a reputation for being strict but fair. My strictness did cause some people to call me a bitch behind my back.
“If I could, I would have Mr. Adams come in here and paddle you as they did back in my day,” I told Derrick. “As much as you need a good paddling, sadly we can’t do that anymore. But I have other ways to punish you.”
Derrick looked at me with a look of arrogance. “Like what?” he asked as if he didn’t care.
“Your scholarship,” I told him with a cruel grin on my face, “I have already called the college and told them I was suspending you from the team along with my recommendation that they pull their offer.”
“That not fucking fair!” Derrick yelled.
He then took a deep breath, paused, and grinned at me; a mischievous grin. “You know, Ms. Monroe, I don’t think I am kicked off the team and I don’t think I will take that detention and I think you will call the college and tell them you were mistaken.”
I laughed at him. “And why should I do that? I have waited four years since you started my school to put you in your place and I finally have you. You are the most arrogant, disrespectful student I have ever seen come through my school. You strut around here like you own the place. You think you can get away with anything based on your looks and charm and ability to play baseball,” I told him and stood up. “Well let me tell you something, young man, you are not all that special. Your charm and looks don’t work on me.”
“I think you need to sit down, Ms. Monroe,” he replied still smiling, “you are going to need it and if you got a bottle hidden somewhere in this room you may want to get it out. You may need a drink after I show you something.”
I didn’t sit down but just stared at Derrick. I honestly did not know what he meant. We were improvising. The only thing we had pre-panned was the scene we set. So far things were going well and I was having fun. In high school, I would have liked to have been a member of the Drama Club but my acting was not good enough so I was always assigned to work on the props.
Derrick smirked at me and reached into his sports bag and pulled out his cell phone. He unlocked the screen, opened up an app on the phone, and handed it to me.
“I suggest you look at these photos I took,” he told me.
I looked at the phone and it was the photo of me wearing my drill team uniform that he took that night many weeks ago. I stared at it not knowing what the boy meant to imply. Derrick answered that mental question I had.
“Those are photos of you and Anthony I took the other day,” he told me. “You think my best friend was not going to tell me that our school’s principal was sucking his cock and he was fucking her?”
I looked up at Derrick with genuine shock. Anthony was his real best friend. I did not expect Derrick to go this route in our game. I played along, however.
“Keep looking at them, Ms. Monroe,” he told me and chuckled. “I got some great shots of you sucking his dick and then him fucking you in the equipment room. He told me you get all horny when you smell the nasty boy’s equipment room and said it’s your favorite place for him to fuck you because of the smell.”
By then Derrick was well aware of my scent fetish. Derrick knew I had it, but never mentioned it and let me enjoy it without teasing me about it. So, when he did that night I blushed, truly blushed, and was embarrassed by it. That added excitement and slight realism to our game.
“I always wondered why you were never married and didn’t seem to date anyone from what I heard,” Derrick continued. “You are attractive for your age. I thought it was because you are just so mean and don’t like people and no man could put up with you regardless of how much pussy you gave him, but I was wrong. It’s because you like teenage cock.” He chuckled.
“These are fake!” I told him and placed the phone on the desk. “Anyone can see that.”
Derrick laughed. “Anyone can see they are not fake and that they are you. I wonder how the school board would react when I email them the photos.” Derrick picked up his phone and looked at the screen. “Nice tits, by the way. I thought they would be all saggy and gross, but they are rather nice, and I love your nipples.”
“What…what do you want,” I said in a defeated tone. “If you think I am going to have sex with you, then you are mistaken.”
Derrick laughed at me. “Oh, we will get to that, Ms. Monroe…” Derrick calling me Ms. Monroe throughout our roleplay excited me.
“This is what you are going to do for me, Ms. Monroe,” Derrick emphasized my name, “I am not kicked off the team, you are going to call the college and tell them you made a mistake and ask them to reinstate my scholarship, and then you are going to change my grades. Nothing drastic, just some C’s into B’s and the two D’s into C’s. That should be good enough.”
“I could get fired if people know I changed your grades,” I blurted out.
Derrick laughed at me again. “You will certainly get fired when they find out you are fucking one of your students.”
I sighed and nodded. “Ok. I’ll do it,” I told Derrick. “I think you should leave now.”
Derrick grinned at me and shook his head. “I don’t think so. There is one more thing you are going to do for me?”
“What…what’s that?” I asked but knew what it was.
“You are going to give me what you give Anthony,” the boy told me.
“I will not!”
“You will or the photos get sent out,” he reminded me. “Now get up and lock your office door.”
I sighed again, defeated, and started to remove my glasses.
“Keep them on,” Derrick told me. “They are sexy and I want you to wear them when you suck my cock.”
I started to take off my glasses as I stood up. I blushed at his words, and put my glasses back on. I then stood up and walked to the door and locked it.
“Now come stand in front of me,” Derrick told me.
I walked and stood in front of Derrick and placed myself between him and the desk.
“Let your hair down,” he ordered me.
I removed the bobby pins from my hair, placed them on the desk, and then ran my fingers through my hair and shook my head to allow it to fall over my shoulders and face. I then stared at the boy.
“Please, Derrick, don’t do this. Don’t make me do this. Surely there is…We…I…there has to be something else we can work out.” I pretended to be reluctant and scared. In truth, I was enjoying our game and extremely turned on.
“Turn around, Ms. Monroe,” he ignored my pleas. “And bend over the desk a little.”
I did as he told me. I looked over my shoulder at him. “You…you will delete the photos after this?” I asked.
“No, I will after I graduate. I still need them to make sure you don’t change your mind,” he told me.
“But…but you won’t show them to anyone?”
“They will be our little secret,” Derick told me and chuckled. “Well mine, yours, and Anthony’s. He was the one who told me to take them.”
“Does…does he know what you are about to make me do?” I asked.
Again, the boy laughed at me. “Oh yes, he knows. He is getting bored with you and thinks you’re somewhat of a prude and won’t do some of the things he wants to do with you,” I flinched when Derricks’s hand touched my butt. “Such a nice ass for an older woman,” he commented. “So since you like teenage cock so much I thought I could help you out since he is going to break things off with you.”
“I am not that kind of woman!” I told him in an indignant tone, “to be passed around like this!”
Derrick chuckled. “You know I do believe that. But don’t worry; I am going to make you that kind of woman. We are going to have so much fun together and we are going to do things you and Anthony have never done.” Derrick chuckled again. “I may even get Anthony to fuck you again with me in a threesome.”
I was shocked by that, generally shocked! I quickly settled down though. I knew it was just part of the game.
Derrick lifted my skirt over my butt to my waist. He had to pull hard because it was a tight skirt. He could have just unzipped it, but he didn’t.
“Nice, sexy panties and stockings and garters for someone who is not that type of woman,” he commented when my skirt was lifted. “Or maybe you were excepting to give Anthony a nice fuck this afternoon and wanted to look sexy for him.”
I blushed, yes for real, as Derrick ran his hands caressingly up my inner thighs. He started at my knees and ran them up slowly over the stockings and I moaned out when his fingers touched my bare flesh above the thigh highs. I bent over a little more and stuck my butt out for him, hoping he was going to caress it. He didn’t.
Derrick sat back in the chair and chuckled again. “So eager, Ms. Monroe,” he taunted me. “There is no need to rush things. Your secretary is gone for the day and no one else is in the offices. We have plenty of time and I am going to enjoy this and you. Now, pull your panties down nice and slow.”
I reached behind myself and slowly pulled my panties down. I gave a yelp, more of a surprise than pain, when my panties were just above my knees, and felt Derrick’s hand slap my butt cheek. The smack stung only slightly and sounded louder than it was. It excited me.
“I said slowly,” Derrick told me. “Pull them back up and do it again.”
I pulled my panties back up and then pulled them down slowly. I assumed I pulled them down slowly enough the first time because I pulled them just past my knees and didn’t get another smack on my butt. In a way, I was a little disappointed.
“Put your hands on the desk,” my younger lover told me.
I paced my hands on the flat of the desk and looked over my shoulder to see Derrick standing up. He got closer to me and started running his hands up my thighs and then my butt cheeks. I turned my head in front of me and closed my eyes tight. I was anticipating another smack on my butt. It never came. Derrick ran his hand down my butt to where the curve of my butt met the back of my thighs.
“You have a nice ass for a woman your age, Ms. Monroe,” he told me.
I then felt the boy spread my cheeks apart to expose both my butthole and my sex for him to look at. I blushed again and yes again it was a real blush. One would think by then and after all the things we have done sexually I would not be embarrassed by being exposed in such a vulgar way, but I was. I still get embarrassed by it even though it arouses me for Derrick to look at me like that.
I heard the boy laugh again. “Well, what do we have here?” he asked mockingly. “Anthony didn’t tell me you had a hairless pussy.” I moaned when he ran his fingers gently up my pussy. “Why, Ms. Monroe, you are such a naughty woman.”
“I…I am not!” I told him.
Derrick just laughed at me and ignored my protest. “Put your hands behind your back, Ms. Monroe.”
I did as he asked and with my hands behind my back I could not support myself so I laid my chest down on the top of the desk. I tried to look over my shoulder when I heard Derrick doing something behind me, but in that position, I could see what the boy was doing. I then felt him grab my wrists and he tied them together with some type of soft cord. It felt like silk or maybe velvet.
“What are doing?” I asked and started to struggle, but Derrick held me in place with his hand on the small of my back until I stopped struggling. He finished tying my hands behind my back. I twisted and turned my hands to try and get free, but the boy had tight them tight.
“I think someone mentioned that I needed to be paddled,” he told me after he had my hands tied securely. “But I think it’s you that needs to be paddled for being such a naughty woman. Fucking one of your eighteen-year-old students, trying to use your power to ruin my future just because you don’t like me, dressing like a prostitute under your clothes, and for having a shaved pussy.” Derrick made a series of “tsk, tsk, tsk” sounds. “Yes, such a naughty woman, Ms. Monroe, and your behavior deserves punishment.”
Derrick stepped away from me and I started to straighten up, but he told me to stay where I was; bent over the desk. I did look over my shoulder before I placed myself over the desk again and saw the boy walk across the room. I saw Derrick take the sorority paddle off the wall, yes I was a sorority girl. It was a novelty paddle I had from my days in college from the sorority that I was a member of. I swallowed and made a whimpering sound when he walked back to me.
The paddle was a thick, wooden, item with Greek sorority letters on one side. It had never been used for the purpose Derrick was going it use it for; it was just a novelty paddle
“Bend over more, Ms. Monroe,” my young lover told me.
I placed my body back over the desk and stuck my butt out and looked in front of me. I again closed my eyes tight and waited for the paddle to strike my butt cheek. I knew he was not going to paddle me hard with it, so I was not afraid at all. I was excited about the prospect of Derrick lightly paddling my butt.
I flinched when Derrick started to caress my butt with the paddle. He ran it gently and caressingly over my right cheek first and then my left cheek. I whimpered again and wiggled my butt slightly in anticipation. I felt the wooden paddle being removed from my butt cheeks and smiled. I was looking forward to the playful punishment.
There was a loud smack and then intense burning pain on my left ass cheek. It was not playful at all! My head and body jerked up and twisted myself to look over my shoulder. I wanted to rub my butt cheek but couldn’t because my hands were tied behind my back.
“Christ on a bicycle! That hurt!” I whined out in a high-pitched voice.
“Bend back over, Ms. Monroe,” Derrick told me. I did!
Derrick had certainly gotten over his squeamishness about spanking me hard. He paddled my butt ten times; gave five on my left butt cheek and five on my right butt cheek. I let him do it! Oh, it hurt, damn did it hurt! Along with the pain I experienced, I also experienced a mess of confusing emotions.
The pain I don’t need to discuss except to say that it was an intense burning pain. The more he paddled me the more my butt became tender and each smack on my butt hurt worse than the one before. What was confusing was the way I felt emotionally.
I felt humiliated that I allowed Derrick to do that to me and did not tell him to stop. I felt ashamed of myself for it turning me on as much as it did. The paddling aroused me immensely. While I am no masochist and Derrick certainly is no sadist, there was just something about him paddling me that had aroused the both of us. It was not something I would want to do often, it hurt too much for that, but I did discover I certainly had a spanking fetish.
It was certainly not the pain that aroused me and I can’t explain why the spanking aroused me when it hurt so much or why I didn’t want it to stop even though it hurt. There are quite a few things I can’t explain that Derrick and I do sexually that I know I should not get aroused from but I do. Spanking is one of those things.
Derrick later told me he had no intention of spanking me that day until he saw the paddle hanging on the wall. I was glad he did. As our relationship continued, I enjoyed exploring our fantasies and fetishes or our fantasies that we thought we would like to act out. Some we enjoyed and others we didn’t.
By the time the boy was done, I had tears in my eyes, a few ran down my cheeks, and my ass felt like it was on fire. While I was not sobbing or crying; I had cried out and made loud whimpers when he was paddling me but did not tell him to stop. I was still whimpering softly and sniffling after Derrick was done “punishing me”.
The boy laid the paddle on the desk and got on his knees behind me. He chuckled and told me my ass was red. I flinched when I felt his hands on my waist and then moaned out when he started kissing and licking my burning butt cheeks. His gentle kisses and licking did not ease the pain, but emotionally it felt pleasant.
Derrick ran his hands down my legs and lifted one and then the other to remove my panties from around my high heels and ankles. He then spread my legs further apart. The boy started licking and kissing my butt cheeks again. I winced when he placed his hands on my butt cheeks, still tender from the paddling, and spread them apart.
Derrick ran his tongue down my butt crack and then I felt the warm, wet tongue touch my butthole.
“No, please. Not there, Derrick, please,” I whined. “That’s disgusting. Please don’t.”
The truth was I wanted him to do it. Yes, I still thought I was disgusting and humiliating, I always would, but it did feel good and turned me on. My pleas for him not to do it were just part of the roleplay we were acting out.
“Now, Ms. Monroe, do you think you have a choice?” Derrick asked me. It was a rhetorical question.
As I mentioned, Derrick and I discussed our fantasies and roleplay scenarios in great detail before we started acting out on them. When I told my young lover some of mine, which always resulted in Derrick being dominant over me, I told him I would be willing to do whatever he wanted, and if I protested it was just part of the “game”. I had complete trust in Derrick that he would not do anything I didn’t want to at least explore. After we did sexual things we had never done before we discussed what we enjoyed and didn’t enjoy. What we didn’t enjoy we never did again.
I discovered I had this fetish about being “forced” or reluctant to have sex with him as part of our roleplay games. Not a fantasy about being taken against my will. I found that very unsettling, but more a fantasy about being blackmailed to have sex and giving in; just as we did that afternoon we finally had a successful roleplay.
The only thing I never was willing to do and explore, even the one time Derrick tried it, was anal sex. I was not going to let the boy penetrate my butthole with his penis. That was a big “no, no” for me. He did try it once and even bought some lubricant for it but I told him no. Derrick picked up the serious tone in my voice and never tried it again.
Derrick ran his tongue around the entrance of my butt and I moaned out when he pushed it inside of me. I moaned out louder when he started fingering my pussy as well.
“Why, Ms. Monroe, your old pussy is so wet,” he said after he took his tongue out of my butthole. “Never expected you to enjoy it so much.”
“I…I don’t,” I protested. “I am only doing this because you are making me.”
I yelped out in pain when Derrick’s hand struck my butt cheek. He was still fingering me with two fingers from his other hand and the sensation of being spanked and having my pussy penetrated by his fingers excited me.
“It’s impolite to tell lies, Ms. Monroe,” he told me and then went back to rimming and tonguing my butthole.
Derrick fingered my pussy with two fingers and kept his tongue in my butt for several minutes. I had my head on the desk and was moaning and whimpering from the pleasure of it.
“Don’t stop, please, Derrick, more,” I pleaded when the boy suddenly withdrew his tongue from my butthole.
The boy chuckled and stood up. “I knew you would like that,” he told me. “I knew you would like your asshole licked.”
Derrick still had his fingers in my pussy but was not moving them. He leaned over my body and grabbed a hand full of hair and pulled my head off the desk. I whimpered from the pain of it.
That was not the first time we explored hair pulling and as with some of the other things we did I discovered I enjoyed it.
Still holding my head up by my hair, Derrick leaned over and put his lips to my ear. “You liked my tongue in your asshole, didn’t you?”
“No, it’s gross and vulgar,” I whined.
Derrick laughed and gave my hair a hard tug and I whimpered again. “Such a lying, dirty woman you are. I wonder how you would like my finger up your ass.”
“No, please don’t do that, please. I’ll…I’ll suck your cock…please just don’t do that,” I begged.
Derrick laughed once again at me, let go of my hair, straightened my glasses that had half fallen off my face, grabbed my hair again, and pulled my head off the desk once more.
“You think you are not already going to suck my cock, Ms. Monroe?” he asked. “I told you I was going to get everything you give Anthony and then more. Do you think today is a one-time-only thing? It’s not. You don’t belong to him anymore. You belong to me and I am going to get what I want from you as often as I want.”
“I…I don’t belong to Anthony,” I told Derrick. “I don’t belong to any man and certainly not someone like you.”
Derrick put another finger inside my wet pussy and thrust all three of them hard into me. I cried out in pleasure.
“No you don’t belong to a man,” he told me. “You will belong to an eighteen-year-old boy after today. After I get you to beg for me to make you cum and have you asking me to put a finger up your ass, you’ll willingly want to give yourself to me.”
“Never,” I told the boy. “I’ll never want you and you’ll never make me orgasm. I find you repulsive and disgusting and vulgar. ”
As he kept pulling my hair, my younger lover started to fuck my pussy with his three fingers. He would pull them almost entirely out of my pussy and thrust them deep inside me at a hard and fast tempo. Over my whimpers and moans of pleasure, I could hear the wet sucking sound of Derrick’s fingers thrusting in and out of my pussy.
“You like that don’t you, Ms. Monroe?” he asked me.
“Uhh…uhh…no…no…uhh, God,” I lied for the roleplay.
“You shouldn’t lie, Ms. Monroe,” he told me. “Liars get punished. Do you want me to stop and paddle your ass again or keep finger fucking you?”
“I…I want you to stop…I want you to leave my office,” I told Derick between my moans of pleasure.
Derrick pulled his fingers out of my pussy. I moaned and came close to begging him to keep fucking me with his fingers but didn’t for our game. Derrick wiped his slick, sticky fingers using my hair to do so.
The boy picked up the paddle and I whimpered again. “No, please not that, please,” I begged.
I was half begging for real and not for the game. I did not think the boy would paddle me again. He did, however.
“I told you liars get punished.” Derrick then paddled my butt again.
Just as before it was five strikes on each butt cheek, but not as hard as the first time. Oh yes, it stung my ass a great deal, however, and did bring tears to my eyes. I begged him to stop; I begged him and was not play-acting. He didn’t however.
He didn’t stop because he didn’t know I was not playing acting. When we discussed our roleplay fantasies we had agreed that I would do whatever he asked and allow him to do whatever he wanted to me even if I told him to stop. We agreed to that because we trusted each other so much and I knew he wouldn’t do anything I truly did not want to. While it hurt a great deal, it still excited me also.
Derrick placed the paddle back on the desk and once more started fucking me with three of his fingers. He didn’t pull my hair this time, however. I was glad about that because my scalp was beginning to hurt badly.
As he finger fucked me hard and fast, the boy taunted me. Telling me how surprised he was that my “old pussy” was so tight, telling me I had a nice ass, telling me he was going to make me cum, telling me how I was going to suck his cock, telling me how he was going to put a finger in my asshole, telling me how he was going to own me, telling me how he was going to paddle my ass when I lied or did not do what he wanted, etc. His humiliating taunts aroused me. I was getting close to orgasm when Derrick moved his fingers inside me.
“Ohhh, my God!” I cried out when he found my G-spot. “Don’t…don’t stop…Ohhh God, baby, please don’t stop!”
“Why, Ms. Monroe, are you begging me not to stop now?” he teased me.
“Yes…yes, please, Derrick, I’m…ohhh my God, I’m so close,” I pleaded.
Derrick had been stimulating my G-spot hard and fast but then he suddenly slowed down the tempo and his fingers left that wonderful spot inside my pussy and he just started to slowly thrust them into me. It felt pleasant but I wanted his fingers back on my G-spot and for him to make me cum.
“Why…why did your stop?” I asked as I panted. “I was going to cum. I was doing what you wanted.” By the last sentence, the words coming from my voice were a high-pitched, extremely whining sound.
“You were only doing half of what I want of you,” he told me. “And only half of what you really want. Tell me what you really want, Ms. Monroe, and you get to cum.”
I hesitated for several seconds as I bit my lower lip and turned my head to look over my shoulder at the boy. I then turned my head back to look down at the desk.
“I…I want…I want your finger in my butt,” I finally admitted shamefully. I couldn’t bring myself to look at my lover’s face as I admitted I wanted such a disgusting thing done to me.
Derrick laughed at me and I felt him dribble his warm saliva over my butthole. I winced and made a long whimpering moan of pleasure as he slowly inserted a finger in my butt. Once his digit was fully inside me, the boy started twisting and turning it. I was humiliated by the pleasure it gave me.
My young lover then started fucking both my pussy and ass with his fingers; three in my pussy and one in my butthole and I started once again moaning loudly from pleasure and calling out to God. He didn’t stimulate my G-spot again, however, but I was still close to orgasm. I wanted a G-spot orgasm though. I desperately wanted a G-spot orgasm.
“Please…uhhh, God, baby…uhhh fuck that feels so good,” I cried out. “Uhhh…please…please Derrick…touch me in the spot…uhhh fuck, please,” I begged.
Derrick suddenly pulled his fingers out of my butt and pussy.
“No…no, please, baby, no!” I pleaded. “I was so close, please make me cum!”
“Who owns you, Ms. Monroe?” he asked.
“You do,” I didn’t even hesitate in my answer.
“Who owns your old pussy?” He taunted.
“You do, baby, please make me cum,” I again begged.
“Who owns that tight asshole?” the boy continued to taunt me.
“You do, Derrick,” I told him in a desperate voice. “Please, baby, I’ll do anything, please.”
Derrick laughed at my despair. I don’t think he knew if I was play-acting or not and honestly, neither did I at that point.
“Stand up and turn around,” he ordered me.
I stood up and turned around in the hope he was going to fuck me on the desk. My skirt fell back down. Derrick sat back down in the chair.
“Lean back on the desk and fuck yourself, Ms. Monroe,” he told me with a huge grin on his face.
“But…but you promised you would make me cum,” I reminded the boy.
Derrick chuckled. “No, I promised you I would let you cum and I will let you. Only you will make yourself cum. Now unbutton your blouse and lift your bra. I want to see those big tits.”
I swallowed hard and unbuttoned my blouse to expose my bra.
“Why, Ms. Monroe, that is not a bra decent women wear,” Derrick teased me. “Or were you expecting Anthony to fuck you today?”
“No,” I answered.
“Now, now, Ms. Monroe, we know what happens when you lie to me,” Derrick said and pointed to the paddle on the desk.
I swallowed hard again. “Y…y…yes I was hoping to meet Anthony after school and hoping he was going to fuck me.”
Derrick smiled. “Well you are going to get fucked but not by him,” he told me. “You want me to fuck you don’t you?”
“Yes,” I admitted.
“In due time. We are going to have much more fun first. Now let me see those tits,” Derrick ordered me. “Anthony said they were not all saggy for a woman your age.”
I blushed at his words and then lifted my bra over my breasts to expose them.
“Fuck, he was right, they are great tits with great nipples,” Derrick commented as he admired my breasts. “Now, sit up on the desk and I want to watch you play with your tits and pussy.”
I lifted my skirt above my waist, sat on the edge of the desk, and spread my legs for the boy.
“Make sure you go nice and slow so I can enjoy watching you be a dirty old woman and get yourself off,” he commanded me.
I then started to do as he told me.
