A cougar age woman that works from home rents out a room to a young college student.
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My name is Jennifer and I’m in my early forties. I had gotten divorced a few years ago and I loved my home very much, luckily I’d gotten it in the divorce, but it was a bit large just for myself. I could afford to keep it, but it was a stretch and I wasn’t sure what to do to bring expenses down a bit so staying here would be more affordable. I worked from home and had a small aesthetics business with an office in the finished basement. I had a few clients come daily for appointments for waxings and massages and manicures and pedicures. I didn’t like the idea of getting a roommate, but the more I thought about it, it seemed like the thing to do to have some extra money at the end of the month.
I wasn’t sure what sort of roommate I’d advertise for, I didn’t really want another woman staying with me, they can be so nosy and petty and all up in your business, yet it wasn’t really safe to have a man stay I knew nothing about. It didn’t have its own entryway or way to keep them off in a separate area. There was a college several blocks away from my home and I thought maybe I should write up a little sign and go post it on the bulletin board inside the school entry way. I’d taken a few self interest classes in the evenings there a few years ago, so knew the layout. I’d taken a couple of stained glass classes and a couple of photography ones.
The next day I wrote up a little sign and walked down with it and put it up. I had no idea what kind of response I’d get, if any. I thought I could offer two choices, one just the room and the other room and board. I liked to cook and bake and could ask for more money if they chose that option. I had my number and email listed on the little sign and went back home and wondered if I’d get any interest.
Several hours later I got a call from a young man named Joe, that asked if he could come by and take a look at the room I had for rent. I said yes, I’d be here all day, the address was on the sign, just come by when it was convenient. He said he’d be over in a couple of hours. A few hours later there was a soft knock at the door and I opened it and there was a very cute, young looking boy there carrying a back pack. I was surprised he looked so young, he didn’t even look old enough to be in college yet. I asked him his age and he said he’d just turned eighteen a few weeks before. I asked him if he was in a dorm currently, or where exactly had he been staying?
He said he’d been driving back and forth daily to his parents home, around forty five minutes each way and he was looking for a better arrangement so he didn’t have to commute. I welcomed him in and he looked the place over, including what would be his room he’d have with his own ensuite bathroom, he said it looked really nice, and I mentioned I was also a good cook and baker and I’d be able to provide his meals if he wanted that option rather than just a room. He said yes, he’d want that as well. We discussed the price and came to an agreement and he asked if he could move in this weekend. I said yes, that was fine.
So he packed up his belongings at home and drove back to my house with them, he gave me first and last and a security deposit and he settled in over the weekend. He tutored on the side for money and asked if he’d be able to bring ones up to his room for that a few times a week and I said yes, that wouldn’t be an issue. No overnight guests, but he could certainly have other students in to earn money.
He was a quiet young man and didn’t cause any trouble, he was neat, didn’t leave a mess for me to clean up and really seemed to appreciate my cooking. I asked him at the start what some of his favorite meals were so I could be sure to have them so he could feel right at home and he gave me a list of his favorite foods and meals and most of them were things I made anyway, so he was a delight to have around the house. Sometimes he’d sit and visit with me in the living room or even watched a movie a few times with me. It was really nice to have someone around the house, and someone so respectful and quiet especially.
My room was down the hall from his. I was used to walking around naked a lot of the time before Joe came to live with me, but I made sure to keep a robe near the door so in case I went out to get a drink or something I’d be covered up. My room also had an ensuite bathroom, so I didn’t need to worry about wandering around in the night, but I did get thirsty at times and would go down and get a drink and bring it back on occasion.
One night I woke up a bit parched and decided to go down and get some of the iced tea I’d made and as I was coming back up to my room I could hear something coming from Joe’s room. I wasn’t sure what it was, but I went a bit closer to see and his door was open just a crack and I looked in. The room was dark other than the glow from the computer screen that was on the desk he was sitting in front of and he was sitting naked in the chair with his young cock in his hand, masturbating as he watched porn on the screen. I was shocked, my jaw dropped. I hadn’t expected to see that. He was so engrossed in what he was doing he didn’t hear me or know I was there watching him. The noise I’d heard was him softly moaning as he stroked himself. He actually had his headphones on, obviously so I wouldn’t hear the moans and groans of the porn actors. His cock was a good size, at least seven inches, larger than I thought he’d have since he was a slightly built boy, maybe five seven or eight.
He had nice washboard abs and was shaved clean. I could see the tip of his cock glistening in the light from the monitor and I watched as he stroked his young shaft up and down and increase the speed of his pumping as he got more and more aroused. Fuck, I was getting turned on just watching him and I didn’t want to leave, but I didn’t want him to know I’d seen him or invaded his privacy. He groaned one more time and then cum shot out of the tip of his cock and down onto his fingers. He grabbed a few Kleenex’s to clean up with and I hightailed it back to my room so he wouldn’t know I’d been there.
I went back to my room and felt so turned on having watched him masturbate like that. I hadn’t cum in over a week myself. I usually made do with a quickie in the shower with the shower massager, or with my fingers, but had just been preoccupied with things and hadn’t made the time to. All I had to do was close my eyes and I could see that young shaft being pumped up and down in his hand. I knew I was wet, and I closed my door and slipped off my robe. I was naked underneath and I laid down on the bed in the darkness and slid my hand between my thighs. I was right, I was indeed wet. I had my feet on the bed, knees up, legs spread and I started to slowly rub my pussy, letting my fingertips get wet from the moisture that was seeping out of my horny cunt. I momentarily wondered if he thought his cougar landlady was masturbating down the hall as he had a few moments ago, turned on by thoughts of his young cock.
My cunt lips opened from their own wetness and I could feel the stiff little bud beneath my fingertips respond as I caressed and teased her out from under her hood. I began to buck my hips up to meet my hand and it felt fantastic as I ground my clit against my fingers. I was breathing heavily as I thought about what it would be like to have that young cock sliding in and out of me, filling me up and going off inside of me. At that age they are horny all the time and he’d be able to fuck a lot. I had to bite my lip to keep from crying out as I came. I came hard and explosively and I know it was because I’d seen that young, hard cock as he masturbated. I fell asleep and woke up a few hours later, still sticky.
I got up and showered and went down in my robe and made Joe an extra nice pancake breakfast. He had no clue how much he’d added to my evening last night by seeing him. He went off to school and I went into his room to collect his laundry and straighten up and clean a bit and I saw his computer was on, so I decided to have a look at his browsing history. I knew I shouldn’t really do that but I was curious. Nearly all the porn links in the history were MILF and cougar porn. I snickered to myself about how much he desired older women, and here he had one right in the house he was staying in, yet he’d not made any sort of a move. Obviously since he thought I’d not be receptive and might kick him out over such an action.
I finished straightening up and left. When Joe came home later he sat down at the kitchen table and I got him a snack, as dinner was a few hours away still. He looked stressed and was telling me about some issues at school and a class he was having problems with. I hated to see him so stressed and asked if he’d like a massage to help him relax, on the house. He looked so shocked, and I said I was a licensed massage therapist, and had my office downstairs, he knew that, I’d shown it to him when he moved in and said I had clients coming a few times a day usually, but I didn’t have any more appointments today. I asked if he’d ever had a massage before and he said no, but he’d always wondered what it might be like.
He finished his sandwich and after I again offered, he followed me downstairs and I said to go behind the screen and remove all your clothes and come out with a towel wrapped around himself and then hop up on the table and we could begin. I dimmed the lights and put on the ocean waves background music I put on to further relax the clients and he looked a bit awkward and as if he wondered what he was getting himself into, I almost laughed at his shy and timid demeanor. He was slim, but taut, with great abs and nice upper arms, I could tell he worked out a bit, but was not overly muscled.
He laid on his stomach and I rubbed some heated oils between my palms and smoothed it over his back and shoulders and rubbed him firmly and rhythmically, spreading the fragrant oils over his smooth, clear skin. I wanted to kiss him between the shoulder blades, but I somehow restrained myself. I could tell from his breathing he was relaxing and giving into my touch. There was no small talk, just deep breathing and I loved to listen to the way he sounded as he fell deeper and deeper into relaxation and my hands moving all over him. I worked on his legs, kneading my hands all over his calves and thighs and wondered if I dare remove the towel draped over him and massage his buttocks. I didn’t want to scare him off by being too forward. Perhaps I should keep this professional, but this little massage would absolutely get me in his mind as someone that could make him feel good.
He rolled over and I then worked on his arms and hands and chest and running my hands over those washboard abs was a treat. I didn’t usually get clients this young, and giving this young lad a rubdown was a highlight of my week for sure! I finished off by rubbing his temples and giving him a scalp massage and I knew he was nearly as limp as a dishrag from my relaxing administrations. When I was finished with him I said he should go have a long, hot shower and I’d go start dinner.
I went back up to the kitchen and made us a nice dinner and I could hear the water running as he was showering. I smirked and wondered if he was jerking off in the shower as I was peeling the potatoes. He came down a while later looking very much more relaxed than when he’d come home a few hours ago and I asked how he was feeling. He said he was feeling very good and much more relaxed than he had in a long time. We had a nice dinner and then he went up to study and I had to work out my finances for the month and then was going to watch a movie.
Joe didn’t come back down that night, he stayed upstairs. I wondered if he was thinking how it felt to have my hands roaming all over his young body? When he came down for breakfast the next morning I asked him how he’d slept, and he said better than in ages, thanks to my massage. He asked me if I got many guys his age coming for massages and I said no, I mostly had middle age women as clients, he said that must be nice, and I laughed and asked why and he said because they were his favorite kind of women. I smiled and asked if he’d been with a cougar before and he blushed and said it had been his dream for several years, but he’d never had an opportunity to be with one before. He’d had a crush on his mom’s friend but kept it to himself. I didn’t want to push him, so I soon changed the subject and he left for school.
I couldn’t stop thinking about Joe, how cute he was, how I was thinking about him more and more as I masturbated, but unless he wanted me as well, I didn’t want to make him uncomfortable around me by being too aggressive. A few weeks past with nothing much happening, so I just thought he’d be a border and nothing more. Then one night there was a soft knock at my bedroom door. I was laying in bed nude under the covers reading and got up and slipped my robe on before answering. I opened the door and he was standing there in his pajama bottoms and nothing else rubbing the side of his neck. I asked him what was wrong and he said he’d slept on his neck funny the night before and it was still hurting him. Could I look and see if maybe I could help it? Of course I replied, come and sit on the edge of the bed.
I got behind him and worked my hands over his neck and could feel the knot in his muscle and started to knead it back into the normal position and he said it helped and felt really good. I laughed to myself and thought I could do other things to make you feel even better. He was so young and beautiful, such clear, taut skin, I started to run my hands over his body, not benefiting his kinked neck in any way. My touch began to turn sensual, and I thought he wouldn’t have come to my bedroom door in the middle of the night unless he was ready for something to happen between us.
Joe’s breathing was deepening as my hands roamed over his shoulders, upper arms and neck. I leaned forward and kissed his neck and as I looked over I could see he had a raging erection in his pajama bottoms. I leaned back on the bed, my loosely tied robe exposing part of one breast, my nipples already erect. He turned and looked at me laying there and I reached out my hand to touch his chest, he climbed on top of me and kissed me deeply, hungrily, like a thirsty man in the desert that was finally given the glass of water he’d been so craving. I opened my lips to him and felt his tongue graze mine. He was so young, so sexy, I wanted him so very badly. I wanted his hands all over me, his cock inside of me. I ran my fingers through his thick hair as we kissed. I could feel his hard cock pressing against my leg, straining to get out of his pajama bottoms.
As if reading my mind, he struggled out of them and kicked them to the floor, and at the same time I undid my robe and removed it and it slid to the floor. He reached down and took one of my nipples in his mouth and caressed my other breast in his hand. God, he was beautiful, looking down at his sweet, young face as he kissed me all over my breasts and down my tummy. He made his way down to my pussy and kissed it ever so gently before opening the cunt lips with his tongue and dipping the tip into my juices and tasting my sweetness. He took his fingers and spread open the lips further, exposing my clit, which he sucked and teased in a very pleasing way.
I could feel I was quite wet and he could see my glistening juices oozing out of me and he made the effort to lap them up and tell me how good I tasted. He came up and slid that sweet, young cock into my pussy and it felt so good, I’d been waiting for this for a few months now and I was relishing every moment of him being in me. He slid in all the way up to the balls and I had my arms wrapped around him, holding him close, and my feet under his ass cheeks pulling him inside of me deeper. Every thrust he was getting me closer and closer to orgasm as he fucked me. I was bucking up to meet his thrusts and could feel his cock grazing against my stiffened clit. As Joe was fucking me, I could feel his warm skin against mine, his breath on my neck between his kisses and the sounds of his pleasure, his moans and groans. His sounds were so pleasing to my ears. I loved the way some men sounded almost as much as they fucked.
It didn’t take too long for me to be pushed over that edge and I came hard. I could feel my pussy contracting around his cock, and that milking soon had him pumping his load of young, teenaged seed inside of me. I could feel the squirts of his cum and I didn’t ever want this to end it was so heavenly. He rolled off of me and we collapsed unto each other, catching our breath and just holding each other. We made small talk for a few moments when he spoke up and said giggling he was hard again already. I smiled and looked down and so he was.
I sat up and schooched down on the bed a bit and leaned over and put my mouth on his still wet, once again hard cock, tasting my own juices on it that were mixed with his cum. He put his hand on the back of my head as I sucked on him, taking as much as I could in my mouth. His deep breathing was turning me on so much as I sucked him, I reached down and started to finger my pussy and tease my clit as I was licking the head of his cock. I took some of my juices on my fingers and smeared them on the tip of his cock and then licked them off, which he seemed to enjoy watching. I maintained eye contact with him as I sucked him and it was so intense and hot. I had a feeling my naughty boy had lots of stamina and I was going to be in for a lengthy evening of fucking. I was right, we went at it like animals in heat until shortly before dawn, when he returned to his room.
I fell asleep and didn’t wake until late afternoon. I was very pleased with this turn of events and wanted us to have lots of sex and fun and maybe more. I wasn’t sure if Joe would ever consider a long term relationship with a woman more than double his age, but we’d have to see where things went. I got up and showered and went downstairs and he was in the kitchen having a snack and I went over to him and kissed him on the cheek and he sort of blushed and asked how his sexy cougar was doing. Still glowing from our night before I told him and he said he had something to ask me and I was afraid what it might be, I thought maybe he was going to ask if we could just pretend like last night never happened and put it behind us or something. I asked him what it was and he said he wondered if he could move into my room with me so we could sleep together every night after we fucked. Oh, I was so glad to hear that. Yes dear, you can move into my room, I told him.
The changes were wonderful for us both, I’d never been so sexually satisfied in all my life, he was fucking me upwards of three times a day, in the morning when he’d awake with morningwood, at night before bed, and sometimes after he’d get home from school, my God, I’d never had so much sex in my life and I was happy with it and with him, he was a sweet and attentive boy, eager to learn and to please, I just wondered what would happen at the end of the school year though, but was hesitant to ask.
Many mornings we’d shower together and fuck with the hot water pouring over us, it was so sensual. He was hard all the time and I was more than happy to service his young cock as often as he needed my attentions. One day he asked about after the school year and said he’d gotten a job to earn money to save for tuition right here in town, a steady tutoring gig and could he stay on? To say I was thrilled is an understatement. I told him of course he could, he could stay as long as he wanted to.
Joe didn’t tell his friends about us, and certainly not his parents, it was our own little world inside the house and a happy one. I loved having someone to love again and cook for and please, it was a delight to have him in my life. I told him I was concerned he was forgoing friendships with ones his own age, but he assured me he much preferred my company and he was very content with how things were. I’m not sure how long things will remain as they are between us, but I guess for right now all I can do is enjoy it and hope it lasts as long as possible. I won’t pressure him or make him feel uncomfortable and risk driving him away. I want to be his oasis when he walks through that door each day. He hasn’t said I love you to me yet and I don’t know if he ever will, I won’t say it either until he does first. I hope that day will come.
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