Night With Mommy

by Sofia Connor

  Class days were always very special and I took extra care to look my best. I did not care if I was over dressed compared to the other students, but I knew that they would always comment on what I was wearing and how could I afford such elegant clothes. I always wore my kid leather gloves and would wear my leather skirts and knee high boots as often as possible.

  I think that many of the ladies accepted me as one of them and would invite me to join them at a local bar after classes. They all thought it was a lot of fun when some guy would hit on me and on how I would play along. I had confessed that I truly loved females and was not gay but I was not sure if they believed me.

  One day I received a phone call from one of the ladies from the class. She wanted some advice on a dress she was sewing for a project and wondered if I could help her because she thought that I was doing so much better than she was. I realized that her curiosity had gotten the best of her and she wanted to see where and how I lived. I was very pleased to invite her over to my apartment that very evening after 8PM which she readily accepted.

  Her name was Annie. She was an attractive brunette in her mid forties with a nice figure and a pleasing smile. I cleaned up my apartment to make it presentable but I did leave enough magazines and pictures and other items that were clearly feminine. I double shaved, got into my makeup and wig. I put on my black satin waist cincher with a black satin garter belt and black stockings and of course my black satin bra. I put on my black soft leather knee length skirt and a blue satin blouse. I put on a pair of kidskin pumps ( I would have preferred to wear my boots) and I thought that I looked sexy.

  I left my bedroom closet doors ajar so you could see the clothes hanging there and had draped a purple satin nightgown over the mauve satin bedspread. I had just received a pair of up to the shoulder black kid gloves from E Bay and I left them on the dining room with the packaging for her to notice when she came in.

  At exactly 8PM, there was a knock on the door and there was Annie. To my amusement and surprise she was also wearing a leather skirt and she was also wearing black leather over the knee boots and a satin camisole. I must have mentioned during one of our classes that I had a particular attraction for leather and that I thought that women were always sexy in leather. I gushed at how sexy and lovely she looked and she returned the compliment.

  She came in with a dress in a garment bag draped over her arm. I told her she could put her coat and dress and things on my bed while I opened up a bottle of wine for the both of us. When she came in the kitchen, she had to mention the beautiful satin nightgown that was on my bed and asked if I wore nightgowns all the time which of course I told her I did. We both took sips of our wine and she touched the black kid gloves that I had left on the table. She put the gloves up to her cheek and said she had never felt anything so soft and how great the leather gloves smelled. She had never seen gloves that long except in the movies.

  I told her that I had bought them on E Bay to wear with my new satin ball gown that I was making for myself. I could tell that she really wanted to try them on and offered to help her put these wonderful long leather gloves on. I could see that the soft leather was having an effect on her as she slid her arms down the leather shaft. I helped smooth the leather up her arm and squeezed the tight leather down her fingers and smoothed out all the wrinkles. She held her arm straight out and took in the aroma of the leather. I said if she put the other glove on that I could take pictures of her wearing them which she readily agreed to.

  I asked her what kind of help she wanted from me and she took a sip of her wine and smiled and made me promise not to tell anyone but she had bought a satin corset online and was having difficulty putting it on. She said that I had mentioned in class that I wore corsets and that I loved them. I told her that I would be happy to show how to lace up a corset.

  We went into the bedroom and she put her gloved hands around my neck and gave me a long wet kiss and thanked me for letting her try the kid gloves on. I helped her unbutton her blouse and draped it on a chair and unzipped her leather skirt and let it fall to the floor. I was pleased to see that she too was wearing a black satin bra and a camisole, a garter belt with thigh high stockings and black satin tap panties.

  I told her that she looked beautiful and we kissed again, this time longer. I could sense that she was enjoying touching me with her kid gloves and she could tell that I was getting aroused. I opened my bureau drawer and took out my own leather corset and would show her how the laces worked. I also took out another pair of kid gloves that were over the elbow but not as long as the pair she was wearing. In the meantime she was checking herself out in the mirror and began rubbing her pussy through her satin panties and moaning. I put my kid gloves on and came up behind her and cupped her breasts with my gloved fingers kissing her in the neck. I knew it would be an exciting evening as she was already trembling in my arms.

  I explained to her how the different sets of laces worked and how to pull each set separately until the desired tightness was reached and how you wrapped the laces around you She had purchased a below the bust corset which was perfect. I loosened the lace and put it around her and hooked all the clasps in the front. I proceeded to tighten the laces as much as I could the first time and wrapped the laces around her waist.

  I asked if she would like it if I took pictures of her in that outfit and she agreed readily. First I had to remove the garters from the corset as she was already wearing a garter belt. As I did so I brushed my hand on her pussy and she grasped it in both hands and started rubbing it vigorously. I took her in my arms and started kissing her passionately holding her face in my gloved hands. Her gloved hands were holding mine and she was all over my body.

  I reached behind her back and undid her bra and let it fall to the floor. My gloved fingers went immediately to her breasts and I took turns massaging them and kissing them. I knelt down before her and slowly took down her black satin panties. Her pussy was already moist as I inserted my two fingers and began a slow rotating motion. I removed my fingers as she licked her pussy juice from my gloved fingers.

  I rose and lay back on the bed and had her kneel astride my chest and guided her pussy to my waiting tongue. I made her love to her throbbing pussy and massaged her stiff little tits at the same time. I could feel each one of her orgasms. Finally she slid off and reached for my cock which had softened up some in the meantime. She put it in her mouth and gently sucked on it until it stiffened again. Then she climbed back on top and slowly descended on my rock hard cock for a nice slow rotating motion. Only a few moments went by when she climaxed again. This time she slid off my cock and put it in her mouth until I blew my whole load in her mouth.

  We spent the night together and did see each other occasionally. I don't know how the other ladies in the class ever found out about it, but from that time on , I had a wonderful clientele of ladies needing help with their "sewing".

  The End.

  Saying Goodbye

  I did some dating in high school but never dated any girl very long. I don't know if it was me or them, but for whatever reason, the relationships just never went beyond casual dating.

  I had plenty of friends who were going steady, hooked-up tight, and just about all of them were having lots of sex but me, well, again casual dating did provide a few hand jobs now and then along with some nice boob action from several girls, even some memorable blow jobs.

  But, well, I wasn't a virgin when I went off to college, I'd gotten rid of my cherry when I was eighteen and a senior in high school to a girl, Melissa Robinson, who was easy to get into bed. Our relationship wasn't serious in the least, I wanted to have sex for the first time and Melissa loved sex. Pretty much all you had to do was ask.

  Well, it was pretty good, she had a pretty nice body and all and she really knew how to use it. So, I did go off to college with some experience at least.

  As many have found out as well, college life and college girls can be much more open and free than what we all had in high school.
I really think a lot of the change that takes place is due to the girls. Once they leave high school and go away to college, they, many of them, let go and begin to have a good time. A really good time.

  That was certainly what I saw and I took advantage of it just like most of my buddies.

  There was one girl, however, that I met when I was in my junior year, she was a sophomore, and we really seemed to hit it off really well. Diana Dolan, like me, was also an English major with an Education minor, we both planned to teach after graduation.

  Diana was really pretty and I soon found out that she had a lovely body that she enjoyed using well and often. I teased her about being "DD with the B's and C's" as a take on her name's initials, her general grades, followed by her bra size.

  It was after a few months of dating that we began discussing more permanent plans and soon after that we became engaged. My parents thought the world of her and when I met her mom, we really connected so it was looking like it would be a marriage made in heaven, as they say.

  Everything was wonderful all the way through my graduation and into my getting a teaching job nearby as Diana began her final year. Then, we both began to see that we really weren't meant to be together and decided to end our engagement and go our separate ways.

  It had been about a month after we'd made our decision, on a Sunday morning as I was sitting at my kitchen table reviewing lesson plans for the weeks to come, when my doorbell rang.

  I hopped up and looked through the little security peephole and there was Diana's mother, Judy, standing in the hallway outside my door.

  Now, I had always gotten along with Diana's mom really well, she was nice and fun and we always seemed to hit it off.

  I knew her mom had been disappointed when we called off our engagement because I overheard her on the phone with her mom telling her after we had come to the decision. Her mom was more upset than we were, it had seemed.

  So, I swung the door open and welcomed her in.

  "Oh, Kenny, I hope I'm not bothering you this morning but I was in town and had some of your things that were still at my house," she said, handing me a grocery bag full of clothes.

  "Oh, sure, gee, thanks, come in, I've got coffee," I said and she stepped inside and we went to my kitchen where I got a mug down. As I turned back to her, she was standing there crying, "Oh, Kenny, I'm so sorry you two have parted ways, I'd so wanted you for my son-in-law."

  I stepped over to her and hugged her to me as I felt her trembling as she sobbed a bit. I held her for a minute or two until she'd calmed down when she said, "Oh, I really should be going, Kenny, I've disrupted your morning enough, I'm afraid. I really just wanted to say goodbye."

  I'm not sure exactly why but I pulled her back to me and kissed her, perhaps a little harder than I'd meant, though maybe not. It was then that I felt her tongue slip between my lips.

  I might have been a little surprised but I was also rather pleased and opened my lips so we could tongue-kiss which it seemed we were both enjoying as we held each other that Sunday morning.

  Without thinking much about it, my hands had roamed downward and were on her butt squeezing and pulling her middle into my middle which, in the long, male tradition, was expanding outward.

  She felt soft and warm and nice, Diana's mother was a pretty woman, trim and shapely, I think Diana had told me her mom had turned forty only a couple of years ago, so she was certainly not old by any means. She felt quite nice in my arms, I can tell you that.

  As we kissed, there was no way she could not have been quite aware of my erection making itself known and when we separated, we just kind of stood there and looked at each other.

  Then, quietly, she asked, smiling up at me, "Kenny, would you take me to your bedroom?"

  The words went directly to my cock. I've told you my exe's mother is a pretty woman and kissing her filled me with sexual excitement like I hadn't felt in quite some time. She was a small woman and nicely curvy and I took her again and kissed her in a very non-almost mother-in-law fashion now with my hands down easing her skirt up to feel her ass in her panties.

  We kissed another minute, then I said, "I'd be very happy and very proud to take you back to my room," and took her hand and led her down the hall to my bedroom, where, thankfully, I had straightened the covers earlier.

  As we went in, she took me again and we kissed as our hands moved on each other working to get one another's clothes undone.

  I had her blouse open and had reached around to unclasp her bra as she got my pants loose and pulled down to my knees. She stepped back and was quickly out of everything but her panties and I stood there in just my boxers as we hugged again and kissed some more, this time with her hand down under my waistband feeling my hardness as my hands fondled her nice warm breasts.

  "I'm not as young as Diana but I hope you'll be happy with me," she whispered as I looked at her lovely body. She was older, yes, but she still had an attractive figure with nice breasts, full with just a bit of under curve. Her nipples were very hard and erect with large pink nipples that I was enjoying rubbing.

  "I've got to say that I'm just really excited to have you here like this. You're really a very pretty woman and I find you very desirable. Very hot," as I kissed her once again.

  I took her hand and led her to the bed and swept the covers back. She got on and pulled off her panties while I dropped my boxers to the floor.

  "Mmm, Diana, of course, had told me how wonderful you were in most things, Kenny, but she kept your lovely manhood to herself. Can't say I blame her," she said as I crawled up next to her and we again slid into each other's arms.

  "I know I'm taking you from your work, but I really just don't care," she said as she moved over me kissing me while her hand moved up and down on my cock.

  My heart was pounding and there was a throbbing in my cock, something that never happened when I was having sex with her daughter. I was so aroused by this forty-something woman, probably much of it in my mind, the taboo nature of what we were doing but, well, it was so hot and sexy to have this naked woman in my bed I could hardly contain myself.

  I'd never been with anyone much older than I was, this was a first for me, especially a woman not far from twice my age.

  "Well, I really was just polishing up my lesson plans and the truth is, I've got just as much time as you have, I really love having you here with me like this."

  She rubbed her body on mine, telling me, "Well, if we have the time, Kenny, I'd make you a very happy man."

  "Oh, for that, I surely have the time," I told her as her tongue went back in my mouth.

  Then she pulled back from my face to say, "For me to make this the best for you, you have to do something for me, you have to tell me whenever you get close to cumming. Can you do that?"

  "Yeah, I guess so, nobody's ever asked me to do that before. This is some kind of thing you like to do?" I asked her.

  "Oh, yes but you'll be the one that really loves it," and she got off me to kneel beside me, taking my cock in her hand and licking around the head as she smiled up at me. Then she tilted her head to lick up and down my shaft as her fist twisted around the head.

  Chapter 2

  Next, she stood up over me, straddling me as I watched her lower herself down, reaching to hold me steady to put the first inch or two up inside her. But that was all. Then she began moving around in a circle while also going up and down on me but just with the top third or so of my cock.

  "Mmm, oh, that's good, really good," I moaned.

  "Tell me if you're close, okay?"

  "Mmm, it's good but no, not yet."

  My hands were on her breasts as she fucked the end of my cock while squatting over me, then she pulled up a little, reached down and swiped the head back and forth in her pussy's wet slit, then around and around in just the very front part.

  Then she got down and sat cross-legged next to me leaning over to suck the tip again, then, leaving it wet with saliva, she held it with one hand and rubbed her
palm around and around just sending my heart rate skyward.

  "Mmm, that's getting me close. You wanted to know," I gasped as she lifted her palm and just barely touched the tip with her index finger, just a little.

  "What is it you're doing to me?"

  "I'm just making it last as long as we can, it really gives me the best orgasms that way and I think you'll like it, too. Every guy I've done this with has wanted more."

  "Mmm, I'm sure willing to try it, it's great so far."

  "Some men don't have the patience but I think you'll see at the end that it was worth it."

  "Yeah, let's go for it. I'm so glad you came by and so glad you didn't have to rush off," I laughed and so did she as she slid her lips over the head of my dick and left it wet. Then she circled it with her five fingertips and began twisting her hand back and forth as she moved so her nipple was near my mouth.

  I had reached my hand down between her opened legs to begin rubbing the wetness up and down. She, like her daughter, was completely shaved. I pushed a finger inside, something I'd found out early on that her daughter liked so much and it seemed from the soft moans it produced, that she liked my fingering as well.

  I knew that what she was doing to me was wonderful. I had learned the valuable lesson that sex, like so many things, is often best taken slowly but this was really erotic. I had never been so highly aroused in my life. She was just keeping me right on the edge of cumming and I had no idea how long she would continue like this.

  "Mmm, I'm getting close again," I told her as she stopped twisting her fingertips around the crown of my dick to begin just slowly, very slowly circling the head with the gentlest touch of her fingertip. That was almost more maddening as I told her again that I was near cumming.