This is a true story of how I started my secret affair with my nineteen-year-old lover, who was eighteen at the time and I was fifty-three, a story of how our affair escalated to helping each other fulfill our fantasies that ranged from normal to taboo. Our relationship is based on about ninety percent sex and ten percent emotion. It is not that we don’t care about one another, not at all; we are very fond of each other. We talk, communicate, have non-sexual fun together, laugh together, go on trips together, and do other things people do in a relationship. We just both know that our relationship is not going anywhere besides spending time with one another and having sex. There is a lot of sex that can exhaust my now fifty-four-year-old body but well worth it.
I like to think the eighteen-year-old boy seduced me and tell myself that often. If our affair was not secret I would tell others that as well. But that would not have been the truth. The truth was there was very little seduction from either of us. It started as a harmless flirtation that led to something more.
As a warning to the readers of this story, some of the sexual play we explore with one another may seem perverse to some and I understand that, it seems perverse to me as well but I enjoy it and have no guilt over it. I just ask that instead of posting nasty comments just don’t read it.
My name is Lori and I am a fifty-four-year-old widow, a mother of two daughters, and a grandmother. My husband died when I was forty-nine. It was not a sudden or quick unexpected death. It was a terrible drawn out painful death from cancer. A couple of years of treatments such as chemo and radiation and several surgeries did little. In the end, hospice came into our home to make him as comfortable as possible for the last months he would live.
I was four years a widow when I had sex for the first time since my husband died. Before that, it had been years since I had sex with him. We used to have an active sex life until he got sick and then it died down and then it became non-existent when his illness took over his body. Sex was not even a priority for me anymore, taking care of my husband who I loved dearly was. I didn’t even think about sex during the worse years of his illness or even after when I was in mourning.
I retired early from my job, having been with the company for twenty-two years I got a full pension. After my husband died I could have gone back to work but didn’t, even though the company I used to work for wanted me to come back. I was very financially secure with my pension and my husband’s life insurance policies and the money we saved and invested during our marriage.
When I was working I made a good salary and my husband had worked his way up in the company he worked for to the higher levels of management and made much better than a nice salary. I decided to spend time with my grandkids and travel.
When my husband got sick and could not upkeep our yard, I always wanted to hire landscapers anyway because we had a large yard but my husband wanted to do it himself. He hired a young boy from the neighborhood to do it. Derrick was a young teenager when he first started helping my husband with the yard work and then as my husband’s illness got worse, took over all the work. It was a lot of work due to the size of the yard and I would help sometimes as well. While it was a lot of work, my husband had the lawn equipment to make it easier including a riding lawn mower.
Over the years I got to know Derrick very well and he grew into a very good-looking boy. Derrick was always so polite and kind and as my husband got sicker he even helped around the house. It took me months to get him to refer to me by my first name instead of Mrs.
We would talk and he would tell me about his school, what girl he was dating, and his friends. I soon thought of myself as a mother figure for him. He lived with his father after his mother left them when Derrick was ten and never wanted much to do with him. I had two daughters, so it was nice to have a surrogate son. My husband enjoyed having another male around the house for a change also.
After my husband died, Derrick could sense I wanted to be left alone and only be with family and while he still did my yard work and a few chores around the house, he left me to my mourning. A few years after my husband died, my daughters thought I should get back into the dating pool. They told me that while I was over fifty, I was still an attractive woman and should meet someone, but I didn’t feel I was ready.
Finally, after four years after my husband’s death, I gave in to their peer pressure and they introduced me to a man at a party. He was nice-looking, a year older than me, and very gentlemanly. I agreed to go on a date with him the following Saturday night.
It was a Thursday afternoon in April when Derrick and I first had sex, three days before my date. Derrick was on spring break from high school. He was in his senior year and eighteen years old. I was fifty-three. He had cut my grass the previous day and that day he was laying out pine straw around my rose bushes and azalea bushes. I opened my front door and told him to take a break and come in for some lemonade I had made. He grinned and said he would rather have a beer and I laughed and told him it was either the lemonade or nothing.
We were in my kitchen, Derrick sitting in a chair at my dinette table and after I gave him a glass of lemonade, I hopped up on the counter. We just started talking about normal things we always talked about. He told me he had broken up with his latest girlfriend. Derrick was not what my generation would have referred to as a player, but ever since he was sixteen he had dated several girls.
I could not blame girls for being attracted to him. He was a very nice-looking young man, charming, polite, intelligent, confident, and respectful. He did have a slight touch of arrogance in him, but just a hint that a lot of girls would find attractive. There were thousands of reasons I was attracted to my husband and his slight arrogance was one of them. Derrick was the type of boy mothers hoped their daughters would date.
He was easy to talk to and had a great sense of humor. After my husband died and after the period of wanting to be left alone and just be with my family, Derrick and I started talking again, and I discovered I could confide in him things I could not with other people. We didn’t share deep dark secrets by any means, just things I used to talk to my husband about. It was nice. I missed that. We formed a good friendship with one another.
I know it’s strange for a fifty-three-year-old woman to be friends with an eighteen-year-old man, but after my husband died I felt out of place with our married friends. I was also getting sick and tired of having to hear them whisper behind my back; “poor Lori, it is just so tragic”, “Poor Lori, how will she ever get on with her life”, and other similar comments. I soon started not spending time with them. Derrick was not like that, yes he was sorry my husband had died, sorry for me and himself since they had become close, but he never showed pity for me. I enjoyed that.
“I have a date this Saturday night,” I told him.
“That’s great, Lori,” Derrick replied. “I know it’s none of my business, but it’s about time you start dating again.”
I laughed. “Have you been talking to my daughters?” I teased.
Derrick chuckled, “No, but if they are the ones who set you up then I agree with them. You are a very pretty woman, Lori, and if I am not stepping out of line, sexy as well.”
I blushed. That was the first time since I had known Derrick that he ever made a comment about my looks and never referred to me as sexy.
“Yeah for an old hag you mean,” I continued to tease him.
Honestly, it felt nice for him to say I was pretty and sexy even though I knew he was just saying that to make me feel good about myself.
Derrick took a long drink of the lemonade, until his glass was empty, and shook his head.
“No, you are not an old hag. I thought you were pretty and sexy when I first met you,” he told me.
“Yes and I was years younger then and also you were a kid who just started puberty so you thought all women were pretty and sexy,” I grinned at him. “Want some more?”
“Yes, please,” he said and held up the empty glass. “More ice also, please.”
I got off the counter, took his glass, filled it with ice and lemonade, and handed it back to him. I sat down in the chair next to his at the dinette table.
“How do you feel about the date?” he asked me.
I shrugged. “He is nice and good-looking, but I don’t know,” I told the boy. “I loved my husband, Derrick, and I miss him a great deal. It’s just a date and nothing serious. I am not ready for serious yet if I ever will be. I am not some young thirty-something divorcee looking to marry again. I was happily married, raised two lovely daughters, and have grandchildren. I am happy with that.”
“I liked him also, your husband. He was a good man, a very good man. My dad thought a lot of him as well.”
“My husband liked your father also,” I told the boy.
I had only met Derrick’s dad twice and never really talked to him, but my husband did and thought highly of the boy’s father. He did d a fine job at raising his son alone.
“Yeah, he’s a good guy,” Derrick said of his dad. “Did the best he could after mom left us.”
I reached over and patted the boy’s hand, “He did a fine job and I am sure he is proud of you.”
Derrick surprised me when he took my hand in his and held it. I didn’t pull away. I felt it would have been rude to pull away. I was raised to be a southern lady with manners and etiquette to go with it.
“Let’s talk about your date,” Derrick smiled at me. “There are other things besides getting serious, Lori. Just have fun. Don’t think of it as a potentially serious relationship.”
I laughed and got up from the chair and poured myself a glass of lemonade and sat back down. I didn’t want the lemonade but used it as an excuse to stop holding hands with Derrick.
“Yeah like you and your girlfriends. How many have you gone out just this year alone?” I asked.
Derrick chuckled. “Only four, but two were just a couple of dates and that was it. Nothing serious, just having fun like I said you should do.”
“I don’t think the type of fun you had with those girls would be the type of fun I would have on my date,” I teased the boy.
Derick chuckled. “It was not like that,” he admitted. “It was just going out and hanging out with friends and having fun. Now the other two,” the boy grinned and did not need to finish the sentence.
“I don’t think I want to hear about the other two,” I told him and laughed.
I was not being indignant or offended in any way. My tone was flirtier to match his. Derrick and I never flirted before and never had a conversation where sexual innuendos were brought up. I used to flirt; I used to be very good at it. I am a southern girl after all and we learn the fine art of flirtation at a young age. I just had not practiced that art in many years and it was harmless fun.
“I would not tell you anyway,” Derrick gave me his charming boyish smile that I have sure melted the hearts of many girls. “Now showing you would be different.”
I blushed again and cleared my throat. “Derrick, I think this has gone too far,” I told him in a calm voice.
“I didn’t mean to offend you,” he assured me. “I am sorry and you are right. I got out of line. I just, well, I have had this crush on you for a while and we were flirting and, well, I am sorry, Lori.” Derrick stood up. “I guess I should get back to work anyway.”
Now I felt bad. Maybe I also let it go too far. I was not totally innocent and could not put the blame solely on him.
“No, sit down and take a break. You have been working all day. It can be finished tomorrow if you have the time,” I told him. “I can fix you something to eat.”
He smiled and sat back down. “That would be great, just a sandwich would be fine.”
I fixed Derick a turkey sandwich per how he liked it, heavy mayonnaise and lite on mustard. He wanted roast beef but I didn’t have any.
I watched him eat and could sense there was still tension between us. I knew he could sense it also because Derrick was normally a talkative person.
“So tell me about this crush,” I asked suddenly to ease the tension and to let him know I was not upset. Derrick choked on the bite of the sandwich he took. I giggled at him.
Derrick stopped coughing and took a drink from his glass. “Are you sure you want to hear it? I don’t want to upset you again.”
I smiled at him. “I was not upset,” I assured the boy, “just didn’t think we should have that conversation and yes I want to hear it. How many times does an old woman get to hear that an eighteen-year-old boy has a crush on her?”
“I wish you would stop that, calling yourself an old woman,” he told me in a serious tone. “I don’t see you as that. Yes, I have a crush on you and have for some time. Not ever since I first met you but as I got to know you and we talked it developed.”
“So what was it, my dazzling personality?” I teased again.
“That, yes, and your looks. I meant it, Lori, I think you are pretty and sexy and you do have a nice body,” he told me.
“Well, I would be lying if I said I was not flattered by that or your crush on me, but I don’t have a nice body,” I told him.
“Yes you do,” Derrick countered, “I have seen you in those shorter shorts you wear when you work in the yard and the tee shirts. I have been over here swimming when you are laying out by the pool and have seen you in your bikini. You have a great body, Lori. You have great legs and I know this may offend you and I am sorry, but you have great boobs.”
I smiled and was flattered I admit, but if he was being honest with me I could be honest with him.
“Yes, but those shorts and the bra under my tee shirt help support things that age and gravity have affected,” I assured him. “I would not call my swimsuits bikinis, but two pieces.” I smiled at Derrick. “You know I can still fit in my drill team outfit from high school,” I teased. I was rather proud of that.
I knew I had nice legs. Tan like most of my body. I liked lying out by the pool and sunbathing by the pool or on the beach. I loved the beach. I was tan but made sure my skin did not become all leathery. I had recently just gotten back from a trip to the Caribbean I took my eldest daughter, her husband, and my two grandchildren on and I had started on my summer tan.
As for my breasts, yes I have always had nice breasts when I started to develop them. They were 36 C cups and tipped with brown nipples. However, my once nice and firm breasts were no longer as firm as they used to be and did drop a little. I meant what I told Derrick – clothes, bras, and swimsuits could give the appearance of things still being in place like when I was younger. I tried to keep my butt firm as well and while still decent looking without clothes; I was fighting a losing battle there also.
“I would like to see that,” Derrick told me and grinned.
I laughed again. “I don’t think so.”
I was enjoying flirting with Derrick and I was flattered he had a crush on me. It was harmless and as I mentioned it had been a long time since I flirted with someone. His being a good-looking, eighteen-year-old made it more fun.
“You know I we are just kidding around don’t you?” I asked to make sure he did not get the wrong idea.
“Yeah, I know,” he agreed. “I know I would never have a chance with someone like you.”
I laughed at that. I had met one of his girlfriends before when she came to pick him up from my house after he did some work on the inside of my house the previous summer. She was extremely pretty and very sweet. I was disappointed in him when he told me he broke up with her, but he told me that her being sweet was a put-on and she was very materialistic, vain, and a bitch.
Derrick was finished eating and I got up and put his plate and glass in the sink.
“The Braves are going to start in a few. Want to watch some of the game with me?” I asked.
I was not a big baseball fan and only watched the Braves play when I went to the games to see them play. I rarely watched them on TV, but I knew Derrick was a big Braves fan. He and my husband used to watch the games together sometimes. When my husband got too sick to even get out of bed, Derrick would sit in the room and watch the games with him. Even though by that time my husband was so drugged up on pain medicine he had no idea what he was watching, Derrick stayed with him to watch the game.
I thought that was sweet of Derrick. Before my husband got too sick, my husband took Derrick and his father to several Braves games along with the rest of our family.
“Sure. I like watching the games on your TV,” he said. I had a sixty-five-inch TV so I could understand why he liked it.
I waited for him to get up but he didn’t. Derrick then blushed.
“Umm, Lori, I think maybe you should go ahead to the den and give me a moment. I don’t think I should get up right now,” he told me.
“Why?” I asked and then it suddenly hit me and I was the one to blush. “Oh!” I looked at the boy. “Seriously?” I asked.
Derrick nodded and I turned my head. “Ok,” was all I could think of to say, and walked into the den.
My intention was not to watch the game nor was it to seduce Derrick. I just did not feel like being alone. Plus, I did want to hear more about his crush on me. I thought it was sweet and harmless and made me feel good. The thought that he had an erection from flirting with me embarrassed the both of us but did flatter me.
“Maybe I should put a towel down or something,” Derrick said once we walked into the den. “I am still sweaty and don’t want to ruin your furniture.”
“Just use the throw on the sofa. I can wash it,” I told him. My eyes did quickly look at his crotch to check and there was no bulge.
I didn’t want to dwell on the boy’s erection, but I did think it was odd how an eighteen-year-old boy could get rid of it that fast and easily. Maybe he just adjusted himself so it would not show. Derrick was wearing a pair of old, worn, baggy cargo shorts so it would have been easy to hide.
I was sitting on the sofa at one end and Derrick sat at the other after he put the blanket on the seat of the sofa. I sat with my legs curled up under me with my back halfway between the armrest and the back of the sofa, just my normal sitting position for comfort, and so I could talk to Derrick without having to keep turning my head from the TV to the boy. I saw Derricks’s eyes glance between my legs. My white, jean shorts had ridden up a little. I blushed again and adjusted myself and pulled the hem of each leg of my shorts down to a more decent length.
We sat in silence for a while and did not say anything. I could tell Derrick was embarrassed by the erection he had gotten in the kitchen and that I knew about it. I did not like the tension.
“Derrick, it’s ok. It happens, especially to a boy your age,” I told him.
He laughed at me. “Oh, God, you are going to give me the talk? I had that with my dad and then the woman’s point of view with my aunt. That was not fun.”
I laughed with him. “Yes, I guess I did sound preachy didn’t I? I just didn’t want you to be embarrassed by it.”
“You were,” he told me.
“Yes, I was,” I admitted. “I am sorry. We should not be. I didn’t see anything.”
“Wow, thanks a lot for that.” We both laughed. “I was not embarrassed by it; I just didn’t want you to see. I am more embarrassed that I admitted I have a crush on you and the things I said about your body,” Derrick told me as he looked at me.
“Don’t be,” I told him sincerely. “I had crushes on older men when I was a teenager. It’s nothing to be ashamed of and I am flattered by it.”
Derrick smiled. “Can I ask you a personal question?”
“Depends on how personal.”
“It’s not dirty or anything. I was just wondering if your hair is naturally blonde,” he asked before I permitted him.
“I swear, Derrick, if you ask me to prove it, I will be mad,” I said sternly.
“Oh, God no, Lori, I would never say that. I respect you too much to say that,” he said defensively.
“Ok, yes it is, but I do have it colored now. Have for years. It’s not naturally this blonde. More brownish blonde.” I stood up. “I’ll show you. Be right back.”
I walked into the home office we had downstairs of our house and got an old photo album and walked back into the den. I sat down next to Derrick. I put both legs on the sofa and crossed them under my butt and sat facing him. He was right, he was sweaty and I could smell his masculine odor. It was not unpleasant at all. I started flipping through the album and found a picture of me when I was in college.
“There, that’s the natural color,” I told him.
My hair was shorter than it is now, a lot shorter, and came down to my shoulders and was styled in the style we had back in the late nineteen eighties when I was a sophomore in college. I had been coloring my hair for years to make it more blonde and it currently came down to the middle of my back and was naturally straight.
“Damn, Lori, you were beautiful,” Derrick told me. “I bet you drove all the boys crazy.”
“Was beautiful?” I teased him.
“I didn’t mean it like that, I mean you are still beautiful and hot and I mean…well you are not even wearing makeup and you look so pretty,” Derrick started to defend himself and talked rapidly.
I laughed. “I was teasing,” I interrupted him before he could say something that would embarrass me and maybe him. “I don’t know about driving boys crazy. That was just after I broke up with a boy I had been dating since I was sixteen and about eight months before I met Steven.” Steven was my husband. “I didn’t date anyone seriously in between.”
The hot comment did not go unnoticed by me nor did the comment about me being pretty even without makeup. Maybe I was still attractive to men at my age. I thought I could be when I wore makeup to hide what age has done to my face. I had two wrinkles across my forehead, crow’s feet around my eyes and a series of laugh line wrinkles on my cheeks when I smiled or laughed. But I was not an ugly wrinkled old hag like I teased about being early. I thought for being fifty-three I was reasonably attractive at least.
“Do you miss it?” Derrick asked. I looked up from the photo album and he was staring at me.
“Miss what?”
“Being umm…well…intimate with someone?” He asked in a nervous voice.
I cleared my throat. “Let me show this picture of me and some friends at a UGA football game,” I avoided the question and started turning pages of the album.
Derrick suddenly showed the confidence and slight arrogance he had. He placed his hand on mine to stop me from turning the pages. My hand felt like it had been shocked by a bolt of lightning but I didn’t move it. Ever since Derrick and I had been flirting all I felt was flattery and some embarrassment, but now I felt something else. I felt something stir between my legs and it felt nice. Okay, maybe I started to get wet between my legs also, but just a little.
“Don’t you miss it, Lori?” Derrick repeated the question but this time with confidence and a slight tone of authority.
“What…how…what do you want me to say, Derrick?” I asked but not in an angry voice but a voice that sounded unsure of myself. “Yes, I miss it. It’s been God knows how long since I was intimate with someone.” I blurted out unexpectedly. “I was faithful to my husband, Derrick, and you know how sick he got. I am pretty sure you know what he could not do…what we could not do.”
“I am sorry, Lori, I didn’t mean to upset you. I thought we were still fooling around and having fun,” he told me. I didn’t believe him.
I snapped the photo album closed and tossed it behind my back on the sofa.
“What do you want from me, Derrick?” I asked in a pleading voice. “I am sorry you have a crush on me, am I flattered, of course, I am. Does it make me feel good and wanted, of course, it does. Then what’s next? What if I told you that I wanted you to kiss me? What then? I am old enough to be your mother. I have two daughters older than you and two grandchildren. You are eighteen. What do you expect? We could date? There was a future for us? You know that would be impossible. What would people say? What would your dad say? What would my family say?”
Derrick chucked at my ranting. It was not an angry rant at all. It was more as if I was trying to convince myself not him. I don’t think he picked up on that, but I was not sure.
“I never thought if anything happened between us we would get serious and get married and live happily ever after,” he told me. “I never thought anything would happen between us at all. Yes, I have a crush on you, and yes I think you are hot and sexy, and don’t give me that shit about being an old woman. You know you are not unattractive, Lori, so stop acting like it.”
“So what then?” I asked, much calmer than I was before and no longer ranting. “Hypothetical, you just have sex with me and wham bam it’s over and everything goes back to being normal?”
“I didn’t say that,” he gave me that damn charming smile of his, “Ok hypothetical then, we have fun as long as it lasts; as long as you want it to last, and then things go back to normal.”
“Derick, we can’t,” I sounded as if I was trying to convince myself again. “You are just too young and I am not that type of woman. Hell, I have only had sex with two men in my life; my first boyfriend and then my husband. It just would not be right and if anyone found out I would be labeled a sexual predator of young men.”
“It’s called a cougar,” Derrick told me and grinned. I could not help but laugh. “Well since it is all hypothetical, I am eighteen so there is nothing illegal about it.”
I just stared at the boy for a moment. I could not deny he was not a good-looking young man, he was. I could not deny that during my entire rant and objections and playing the hypothetical game, I was not getting aroused and the smell of his masculine scent from his sweaty body was pleasing to me.
“So what now? Hypothetically, what do we do now? I just kiss you and then we go at it? I have not done this in so long and I don’t know how it works these days with you young kids,” I tell him in almost a whisper.
Derrick again chuckled at me, “I am sure it works the same way as it did when you were my age,” I smiled at that. “Do you want to kiss me? I am not asking hypothetically.”
I bit my lower lip and nodded my head. Derrick smiled, moved his body to face me more, and lifted his hand. I flinched out of nervousness when he touched my cheek and gently and brushed my hair behind my ear. When he leaned in to kiss me I moved my head forward to meet him. When our lips met it was timid at first but soon I parted my lips and he did the same and our tongues entered each others’ mouths. I wrapped my arms around his body as we started kissing with more passion and intensity.
God, it felt so wonderful to be kissed like that again. I loved kissing and it had been so long since a man kissed me like that. I made a series of moans into Derrick’s mouth as we kissed and he put his arms around me. I started to lean back, uncrossed my legs, and pulled Derrick down as I spread my legs apart to allow his body to lay on top of me. I moaned louder when he started kissing my neck.
“Stop, wait, baby, stop for a second,” I told him.
Derick lifted his head and looked down at me. “We don’t have to do this, Lori,” he reassured me. “If you don’t want to we can stop.”
I smiled at him. “No, it’s not that,” I told him.
I raised my body slightly and reached behind my back. I pulled the photo album form behind me and tossed it on the floor.
I giggled. “It was digging into my back,” I said and pulled his face to mine and started kissing him again as I laid back down.
We kissed for a while and Derrick once more started kissing my neck. I moaned out and ran my hands under his tee shirt. When his lips touched my ear lobe he started to suck it and I squealed in pleasure. My ears were one of my erogenous zones and I loved them kissed and sucked. Derrick drove his tongue into my ear canal. I squealed out in pleasure again and thrust my hips up into the boy.
“Ohh, God, yes…oh, yes, baby,” I moaned out.
Derrick gently bit my ear lobe, causing me to once again make the squealing moan, and he gently pulled it with his teeth and then let go. God, it felt wonderful!
“We can stop anytime you want,” he whispered in my ear and then lifted his head to look at me.
I was beyond the point of stopping in just that short period. I didn’t want to stop! I let him know I wanted to keep going; I placed my hand on his face and pulled his face to mine to kiss him once again. I then took his hand and placed it under my tee shirt and pushed my bra above my breasts.
Derrick took the hint and started playing with my nipples. I moaned out even louder in ecstasy at his touch. I started kissing his neck, licking it to taste his sweat and the dirt on his body. I moved my right hand between our bodies and started feeling around below his waist and quickly found what I was feeling for. I started rubbing his penis through his shorts and underwear. It felt big and was so hard. God, he was so hard and I loved the feel of it!
Derrick made a masculine moan of pleasure. A sound I had not heard in so long and it excited me and I gripped his penis harder and started massaging it faster.
Darren moved his head down lower, lifted my tee shirt, and stared at my breasts. I was still rubbing his penis, not ever wanting to let it go. I bit my bottom lip in nervousness as the young man stared at my breasts. I hoped he was not disappointed with them due to my age.
“Fuck, I knew you had fantastic tits, Lori,” he told me. “The tan lines are so sexy.”
I smiled and grabbed his head and pulled him down to my breasts. I let out yet another loud moan of pleasure when his mouth attached to my right nipple and he started to suck it. I gripped his head with one hand and his penis with the other as he sucked one nipple and then the next. I gasped put in bliss when he gently bit each one in turn.
“Your brown nipples are so perfect, Lori,” he told me as he looked up at me. “They are so hard and so big and puffy when they get hard.”
“More, please, Derrick, more,” I begged him. I wanted him to suck and lick and kiss and gently bit my nipples more.
As Derrick used his mouth on my nipples, I let go of his penis and wrapped my arms around his back and my legs around his lower butt. I started trusting my hips up into him and he started grinding him into me. My sex which had been just slightly wet earlier was now extremely wet. Derrick took his mouth off my breasts and started kissing me again. After several moments so us making out and grinding into one another, Derrick sat up to kneel between my legs and placed my legs over his thighs. He then started to unbutton my shorts.
“Stop, no, stop, Derrick,” I asked him.
Derrick stopped and looked at me for a second or two. “Are you ok?” he asked. “We don’t have to if you don’t want to.”
That was sweet of him. I grinned and nodded my head.
“I am fine and I want to, I want too badly, but I want to do something first,” I told him.
“What?” he asked me curiously.
I blushed but answered him. “I want to use my mouth on you. I want to put it in my mouth.”
“You want to suck my dick?” he asked and smiled.
“Yes,” I answered.
“Well, I am not going to say no to that,” he grinned and I giggled.
Derrick sat up on the sofa and put his legs on the floor and started to take off his shorts.
“No, I want to take them off,” I told him and he stopped.
I got up and got on the floor between his legs and looked at his face while I unbuttoned his shorts. I was smiling at him.
“Are you sure you want to do this?” he asked.
I rolled my eyes, “It may have been a long time since I did this and I may be out of practice but yes I want to,” I assured him.
“I’ll tell you when I am about to cum so I won’t cum in your mouth,” he told me.
“Derrick, baby, I want you to do it in my mouth.”
The boy grinned and leaned back on the sofa as I pulled his shorts down and then his underwear. His penis jumped out of his underwear and almost hit me on my nose. I made a gasp. He was bigger than I expected. Bigger than both of the men I had had sex with.
He was not huge or too overly large that I was afraid I could not fit him in my mouth or inside me when we had sex, but larger than I thought he would be. It was a nice big not an intimidating big. He was about seven and a half inches, maybe eight. Later in our affair, I found out he was just a tad bit over eight inches when I playfully measured him one night. The girth was nice but again not overly large. It was smooth and not veiny and the head of his penis was just perfect and not a big mushroom-type head as my first boyfriend had. I did not care for that look of a penis. I thought it was a very nice penis.
I gathered my hair behind my head and quickly looped it in a knot to keep it out of my face.
“Can I just touch it for a moment before I put it in my mouth?” I asked Derrick.
“Lori, you can do whatever you want. Tale all the time you need.”
I smiled and took his penis in my right hand and placed my left hand on his knee. It was so warm and hard. I had forgotten how warm an erect penis could be. I stared at it as I started to slowly glide my hand up the shaft. Slid my hand up and down his shaft a few more times and then sat up on my knees, lowered my head, and took the boy’s penis in my mouth. The scent and taste of his sweaty crotch were more pungent than they normally would have been, but I liked it.
I started slow at first, keeping my hand at the bottom of his shaft, to get used to doing something I have not done in about eight years. Derrick let out a moan as soon as my mouth touched his penis. I took the top of his penis in my mouth and ran my tongue over it, tasting his pre-cum. It was not long before I started bobbing my head up and down slowly, taking about four or five inches of him in my mouth and down my throat. I had forgotten how much fun it was to give a blowjob.
“Oh, fuck, Lori, this feels amazing,” Derrick told me.
Encouraged by the young man’s words I started going faster and was surprised and glad I didn’t gag as I increased my tempo and took more of him down my throat. I guess it was like riding a bike, you never forget how to do it. When I felt saliva build up in my mouth, I let some of it drool out and coat Derrick’s shaft and started using my hand as well as my mouth to give the boy pleasure. I always liked giving a sloppy blowjob. Derrick made masculine moans as I sucked his penis.
After about five minutes, I was going to try and deep throat the boy, but before I could, Derrick placed a hand on the back of my head, not to force me to go further down but lightly rested it there to guide me.
“Uhh, fuck, I’m going to cum, uhhh, God, I’m going to cum,” Derrick groaned.
I lifted my head and had about three inches of the boy in my mouth and started stoking his penis hard and fast. Derrick made a series of grunting sounds and he exploded his cum in my mouth. I found his masculine grunts and moans sexy. I always enjoyed hearing a man cum and listening to a man moan and grunt and groan in pleasure when he had an orgasm or when he was having sex with me.
I felt his warm, thick, fluid hit the back of my throat and the roof of my mouth. I was sucking and using my hand as I kept swallowing cum the boy shot into my mouth. Derrick’s orgasm lasted a nice, long time and he shot an abundance of cum into my mouth. I swallowed all of it and highly enjoyed the taste and texture of his cum.
When Derrick’s orgasm ended I took my mouth off of his penis, swallowed two more times, and stroked his shaft to milk more cum from him. Two drops oozed from the boy’s penis and I licked them off and swallowed again.
“Damn, Lori,” Derrick said between deep breaths and I looked up at him, “that was fucking amazing. I’m sorry I came so fast but I couldn’t help.”
I smiled, “It’s fine, baby, it was very nice and I enjoyed it immensely.”
Derrick ran his hand over my cheek and caressed it. “I never would have thought a woman like you would swallow,” he told me.
“A woman like me?” I teased him as I lowered my bra and tee shirt over my exposed breasts.
“I mean…I didn’t mean to imply, I meant,” Derrick started to stammer, “I meant a woman so respectful and prim and proper and ladylike.”
I laughed and stood up and straddled the boy’s lap. His penis was still erect and for half a second that surprised me, but then I remembered he was only eighteen. I briefly wondered just how long he could sustain an erection after he had another orgasm. The thought excited me.
“You are sweet, baby,” I told him as I wrapped my hands around his neck. “I may not have been with a lot of men and honestly have not done a lot of things sexually beyond the norm, but I’m not a prude and I do know foreplay and sex can be a great deal of fun and it should be fun.”
Derrick grinned and placed his hands on my butt cheeks and pulled me closer to him. I leaned in and kissed him passionately.
I ended the kiss and leaned back. “Do you want to go upstairs to my bedroom and have more fun?” I teased.
“Only if you’re sure you want to,” he answered.
I giggled. “Baby, if I didn’t want to I would not suggest it.”
I got off of the boy’s lap and started walking out of the den. I stopped at the entranceway to the den and looked over my shoulder and saw Derrick pulling up his underwear and shorts.
“Well, are you coming?” I asked.
Derrick grinned. “Oh, I’m sure I will, more than once,” he teased and I laughed.
The young man quickly stood up, walked to me, and I took his hand in mine and led him out of the den and upstairs to the bedroom.
