My Threesome with Mom and grandmom
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My Step Mom And Me free porn video
When I first met the lady that later became my step-mom, I was 12 yrs old. I thought she was okay looking, since she was a bit over weight, but her oldest daughter, BOY, she was a KNOCK OUT. Her youngest daughter, she just looked like a normal teenage girl, but nothing really to make your head spin twice.
My dad would drive out to her house (she lived out in the country, about a 30-minute drive from where we lived at in town), usually 2-3 a week, and we usually stayed late, with the 2 of them watching TV, and talking and stuff. On school nights, if we stayed out there late, I was told to go to sleep in the younger daughter's bedroom (Shannon.) Dawn had her own bedroom, which was much bigger, and less crowded, but I think they knew if I slept in there, I would try to work up the courage to make a move on her (Dawn,) not that she would ever go for it, as she was a goodie-to-shoe, all the time I knew her.
My dad and Lynn (step-mom) dated for a few years, before he moved down to live with my grandparents, while he worked in Wichita, Ks. Wichita was about 3 ½ hours away from where Lynn lived, but every other weekend, he would drive up and visit her, while I stayed with my grandparents. I kind of hated that, because I wanted to go, so I could possibly go horseback riding. He worked in Wichita for almost a year, before Lynn came down, and they rented a hotel room in Wichita. When they did, they also got a room for me, so I could go over there and go swimming, and be a bit free of parenting supervision.
During my time in the pool, a girl about my age was flirting with me, I at that time, I was all hip about myself, no shyness, ready to go for anything, no matter what. Anyways, we are splashing around in the pool, and playing around, when she submerged me, than followed after me, and kissed me under water. When we surfaced, I told her if she kept that up, she might be in trouble. She did this a few more times, with following up on the kisses. (I am not sure where her parents were, but I think they were on the opposite side of the pool, where they couldn't see us.) After about the 4th time, I decided if she was going to keep this up, than I am going to have a bit of fun, and see if I could feel her up. Not only did she let me, but she also pull the crotch over, so I could fully finger her. After about 15 minutes of this, she asked me to escort her up to their room, because she needed to get something. Hate to say, but we didn't do anything while in the room (I think I could have, if I would have just gone for the kiss, and feel.)
Fast forward 6 months, and that is when I found out that when Lynn was down visiting, her and dad had gotten married. Now, we were getting ready to move to Texas. Mind you, I had stayed late over at Lynn's, and even had some scolding from her, but never as a parent, and I had never had sisters before. The house they bought, and we moved into was a 4-bedroom, 2 car garage, with a gameroom above the garage. All of us k**s had bedrooms upstairs, while dad's and Lynn's bedroom was basically right at the foot of the stairs. So, if their door wasn't shut, you could basically see into the room, without much obstruction. And believe me, there were quite a few times I enjoyed that, as Lynn wouldn't have her bedroom door shut all the way while she was in her bra, or even braless, while I came downstairs.
At that time, I knew about sex, but had never gotten to 3rd base with any chick. Infact, I didn't hook up with anyone, until my Freshman Year JROTC Ball. And what made that night so special, was the girl I fucked, was already a good friend of mine, and was close with my best friend, and his twin brother. My best friend's twin brother, myself, and Sherrol were all in JROTC, therefore we all attended the ball that night. It was arranged with the parents, that my step-mom would pick up Brent, and Sherrol, and take us all to the ball, and Sherrol's mom would pick us up afterwards, and we would stay the night at her house (the ball wasn't to get over until 130am, and it was a Friday night, and with Brent's parents having to work the next day, and my step mom knowing she was going to be up late grading papers (She was a school teacher), she would want to sleep in.
At the ball, Sherrol and I were dancing, and stuff, and I just came out and asked her if she would like to be my girlfriend, which she replied, “I was hoping you would ask sometime, and was about ready to give up on waiting, but yes, I would love to be your girl.” We ended up breaking a few of the rules set forth by the school, and JROTC Colonel, but we didn't mind, since we didn't get caught. On the ride home, she asked that Brent and I ride in the back, so she could talk to her mom, which we agreed to (at this time, Brent didn't know I had asked her to be my girlfriend.) I guess on the way back to their house, Sherrol asked if it was okay if we screwed around that night, because once we got to the house, she told Sherrol that she and I could use her room that night, while Brent slept in Sherrol's bedroom, and she would sleep on the couch. Needless to say, Sherrol and I didn't get much sleep that night, and her mom never once interrupted us, nor made any comment on us making so much noise, the next morning. And Brent, well, I guess he was to beat, because he was none the wiser, until about a week later, when Sherrol and I went out, and did some cruising, before going to the lake and did some parking. We ended up being together until I got sent away to a boy's home, because of all the stuff I was doing, and how I was rebelling against school.
After I was emancipated, I moved back up to where my parents lived, and for a few weeks, stayed at their place, until I could get a job, and rent a place I could afford. During that time, I was sleeping downstairs, in the living room, on the couch. The only bathroom downstairs was adjoining to their bedroom, and had an entrance from both the hallway, and their bedroom. And as one knows, when one gets up, the first place to go is to hit to head and relieve themselves. A couple of times, unbeknownst to me, until I had opened the door, my step-mom would be standing there, usually topless, without a bra, and a few times, I even got to see her naked. I thought I had had fantasies about her before – when I had seen her tits, either covered in her bra, or uncovered, those compared nothing to these new ones.
Nothing happened, and I eventually moved away, but since I was always close in communication, and could open up to my step-mom about most things, I usually called her a couple times a month. When I moved out of state, that died down to once every few months, until I found out that she was having some health issues.
By this time, I was around 22 years old, and she was in her late 40's, I believe. I was on my second marriage, and it was not going that well, and I told her so, and we started speaking about why, and somehow, sex came up in the conversation (not sure if it was her, or me, that brought it up.) We discussed things like how I was getting flustered, because Della (my than wife) wasn't putting out, when I was home (I was an Over-the-road truck driver at that time, usually gone Sunday nights, until Friday late nights, sometimes Saturday mornings.) She told me about how my dad had been neglecting her needs, for a few years, and how she felt like she wasn't attractive anymore. I told her that was far from the truth, because if she and I weren't married, and I wasn't her step-son, I would be trying to hit on her so hard, she would barely know what had hit her, until the next morning, when she would wake up so sore from the screwing I had given her the night before.
We also talked about what parts we enjoyed in relationships, and even in sex. She told me that she couldn't give much of anyone an intimate kiss, because that was one of her hot zones, as well as kissing on the back of her neck, and nibbling on her ears. She also told me that she had a difficult time, when it came to having an orgasm, because no one knew how to hit any of her hot spots, like sucking on her tits when they were being intimate with her. Plus, she had never really had anyone perform foreplay on her, so she didn't know what all exactly was a build up to the intimacy, other than kissing. We got to where we were talking pretty freely about sexual things, that we enjoyed, or might enjoy, and might want to try – at some point in our lives.
After about a year and a half of all the talking, and my lead driver was on his vacation, I had a substitute lead driver, and we ended up having a pick up from south of where she lived, and we had to come thru her town, on the return home. So, I suggested to the lead, that we stop in and visit with her, and we could grab a bite to eat, at the same time, which he agreed to. So, I called her while we were still a few hours out, and told her we were planning on stopping in, and I wanted to visit with her, over dinner. She told me she would be happy to see me and let me know when we got to someplace close by to park. Well, I figured there was an old strip mall down the street from the house, and it would be easy for us to stick out to her, and we parked there, and I went to the station and called her. She came and got us, asked us what we were in the mood for, and we headed to Chili's. I introduced her to the other guy, told her he was a substitute lead driver, while my lead was on vacation. When we got to Chili's, she insisted we order whatever we wanted, she was going to get the tab (even thou I argued with her about it, almost the entire meal, she still wouldn't let me pay for it.) We spent an hour, maybe a little longer eating, talking, and catching up on a few things – than she took us back to the truck, as we really needed to get back on the road, as we had already stayed longer than what the company wanted us to allow for eating times. Since the truck had been shut off, and I had released all the air in the air tanks, I opened the doors, started the truck, so it could build air back up, and then went and told her good-bye. As I was leaving, I gave her a peck on the cheek, and started back for the truck. As I was about ready to climb in, she honked the horn, and motioned me back, and asked me what type of kiss was that. So, I leaned in, and was planning on giving her a peck on the lips, but she caught me by the neck, and started an intimate kiss. After a few minutes, she released me, and all I could say, was “Wow'. I leaned back in, and gave her another deep kiss, which she reciprocated, and when we broke, I told her I enjoyed that. She told me, that gives you something to look forward to, if we ever go any further. Needless to say, it was real fun trying to get back in the truck, hiding a woody from your co-driver – knowing your own step-mom gave you.
Fast forward a year, and I was driving for a different company, but this time, I not only drove a truck, but it was doing road resurfacing, and we went out of state to do jobs, as well as in state. In the time since I had visited my step-mom, we had talked more, and we had even discussed what it might be like, if we ever had time to ourselves, since I traveled without my wife, and my dad – like a dumb fool, even thou still married to, was living someplace else. I asked her, if she really would want me to come and visit, if I had the chance, which her reply was undoubtedly, Yes. So, I was in Oklahoma City, and the company works for 2 weeks straight, than on Friday afternoon, the company clocks out, and doesn't return until 10am Monday. Well, with me being only a few hours from Dallas, I called her and told her if she wanted, I had the gas money for round trip, plus some extra to do other things, if she wanted to come and get me. She told me to give her a few hours, so she could call my dad, and they would both come and get me. Hearing that, kind of sunk my expectations – which later, come to find out, it shouldn't have.
On the way back, dad, himself, told me that right now, he and Lynn were split up, and where he was staying, since he had roommates, they didn't have room for me, so I would have to stay with her. Than he proceeded to tell me had plans all weekend, and with his work schedule, he wouldn't be able to accompany us back to Oklahoma City. Otherwise, we just chatted about this and that, all the way back to Dallas. Lynn and I dropped off my dad at his place, and she asked if I minded if we stop at a little club in the neighborhood, which I replied no. We stopped, and she knew the bartender, and I asked him if he knew how to make a 57'Chevy, which he assured me, he did (needless to say, no, he didn't.) Lynn ordered her usual, a Strawberry Daqarie. She drank that one kind of fast, I thought, and we danced to a few songs, than she ordered another and downed that drink. When we were getting ready to leave, she asked me if I minded driving, and I told her I had better, with the way she downed her drinks.
Even thou I was raised in the Dallas area, and had known most of the area when I was a teen, this part of Dallas I didn't know, so she had to give me directions on how to get back to the Interstate. Along the way, she told me to pull into a 7-11 and get a couple of boxes of condoms in case we did do anything – since she was still capable of becoming pregnant. That kind of shocked me, knowing she was actually thinking about taking our talks to the next step.
Once we got back to the house, I opened the door, turned on the lights, and went back out for my overnight bag. She went in and asked me if I wanted a beer, or something to drink, which I replied tea was just fine. She went and got our drinks and went into the living room, and when I came back in, she told me to just set my bag down by the door, we will deal with it later, as she just wanted to sit and talk and catch up on what had been happening in my life. So, we both sat on the couch and talked for a little while, about this and that, when all of a sudden, she asked me, out of the blue, if I really did find her attractive. Of course, I couldn't lie to her, so I told her the truth – that if it wasn't for my dad, I would do about anything to hook up with her. She scooted closer to me, and replied that my dad wasn't there, so what was stopping me. So, I leaned over and started off with kissing her. I first gave her a sensual kiss on the lips, worked my way back to her ear, than her neck, and back to her mouth for a passionate kiss. I could tell by her breathing she was getting excited, and when she kissed me back, I could have sworn she was trying to rip my tongue from my mouth.
As she was wearing a skirt, and a button-down blouse, while I was still kissing her, I undid a few buttons and reached in and pulled one of her 42D sized tits from her bra and started to massage it. I worked it over from the base to the nipple, and even gave the nipple a few tweaks, making her gasp, each time I did. After I felt I had her plenty ways warmed up, I withdrew my hand and put it under her skirt and reached up for her panties. I got what I expected – drenched crotch. I pulled them aside, and played with her pussy for a bit, until she bit down on my lip and climaxed. Afterwards, she told me to keep those thoughts, while she went and got changed.
At the time I was visiting, she was living in one of the upstairs bedrooms, and the room she told me I was going to stay in was downstairs, right next to the front door. After about 10 minutes of waiting on her, I began to think she had changed her mind, and was getting up and getting ready to grab my bag and head to bed. Just as I got to my bag, she called my name, and I looked up to see her in an outstanding nightie. It was nothing super sexy, but to me, it made her body stand out more fuller, and drew out all her curves just right. She asked me where I thought I was going, and I simply told her that I was beginning to think she had changed her mind about things. Her reply was simple...”How could I, when you got me so worked up I creamed my pants, and am desperately needing the feel of a real cock.”
When she came back downstairs, she grabbed my hand and led me to the bedroom, and asked that I keep the light out, while she got disrobed, so I did. But, there is a street light almost right outside, and the blinds didn't do much to discourage any light, so I got to see plenty of her, and believe me, I liked what I saw. When she laid down on the bed, I started to get undressed, and afterwards crawled on the bed with her. I resumed kissing her, and got her worked up again, but inside of using my fingers anywhere on her body, I slowly made my way down her body with slow, wet kisses. I stopped and sucked on her tits, as well as nibbled on them, both seeming to bring deep grunted gasp from her. After paying attention to both her tits, I resumed my trip and worked my way down to her deliciously, wet pussy. She told me she wasn't really into oral foreplay, but I went ahead and started my bit on eating her up. For someone that wasn't into oral foreplay, she got off 3 times, before she begged me to stop, and to please make love to her.
When I crawled up, she asked me to be easy with entering her, as she hadn't had sex in over 6 years, so I tried to slowly enter her, but she was juiced up enough, it was easy to slide right on in. We made love in the missionary position for about ½ and hour, before I asked her if she would like to do it in any other position. She told me that the only other position she knew was on top, facing my feet, but she couldn't get off that way. So, I told her instead of facing my feet, turn and face me, while on top, and we would remedy her not getting off while being on top. She slowly lowered herself on me, and when she reached the base, that was when she realized, I was the biggest cock she had ever had. I was actually topping out against her cervix, and according to her, it wasn't painful, instead, it was highly erotic, and made her feel more delighted.
She rode me, at her own pace for about 15 minutes, when she cursed that she would get right to the edge of building up a climax, and than it would just fall flat out. I told her the next time she got that high feeling, let me know, and let me take over her movements, and how she is positioned in leaning. The next time she got to the edge of a pending build up, she told me, so I grabbed her ass, and one hand on her back, and leaned her forward some, and picked up the pace of the stroking. Within a few minutes, I could hear her building up to a delightful cum, and I could also tell, she wasn't a gasper, or a clincher, but she was a screamer. And believe me when I tell you, when she got off, if anyone else had been in that house, they would have known she just came, like her life depended on it. I was surprised even, that the neighbors didn't hear her.
We kept at it, off and on, most of the night. If I got soft in between, during our breaks, she would give me a hand job to get me back up. But, we finally finished around 5 in the morning.
When I woke up, around 8:30, she had already gotten up, taken a shower, and was making breakfast for us. She wanted to go ahead and keep my original plans of an excuse to come down, so we got ready and went to the amusement park, and spent the day. Instead of going home and fixing something to eat, I decided it was my turn to treat for dinner, and it was up to her to pick a spot – I told her not to worry about the cost, as I was prepared to spend whatever on her for the weekend. She picked a nice 4 star restaurant, and we had a few drinks with our dinner, and laughed about a few things that we had done that day. Also discussed when I had to be back, if we regretted the night before, and if not, would we want to repeat the episode. I told her I had no regrets, and most definitely, I would love to repeat it, as many times, and whenever we could. After dinner, we headed home, and we decided that the previous night was just not enough, and that we would spend the night together, again.
When we were getting ready for bed, I asked her if she would mind giving me head, which she told me she didn't mind giving head, in fact, she enjoyed it, but she couldn't handle someone cumming in her mouth, or the taste of it. So, she started giving me head, and boy, could that woman give head. After only a few minutes, I had to tell her to back off, otherwise she would get a mouth full, so she did. That night was also the first night she was introduced to a few new positions, as she had told me earlier that the only 2 positions she had ever tried was missionary and reverse cowgirl. She found out that she liked doggie-style the most, and also that she was a squirter. When she came that night, she came so hard, so many times, we had to take the mattress out afterwards and let it air out and dry. So, that night I ended up sleeping upstairs, in her bed. I definitely loved snuggling up and spooning with her all that morning.
The next day, we ran a few errands, and I got some items I had been wanting to get for a while, since I didn't visit Texas much, and had to do some chores and my laundry. Let's just say, she made sure ALL my laundry was washed, before we left to go back to Oklahoma City. She even offered to come upstairs to the shower, and wash me, but would not join me in the shower. I did my darnest to get her in, but n matter how hard I tried, she refused. That night, we didn't do anything, as we had to leave at midnight, so I could get back to the job site on time the next morning. But, she offered to give me head, on the way, if I didn't allow others to see what she was doing. I couldn't turn that down.
We left at midnight, and shortly after we got out of the burbs of Dallas, she reached over and undid my pants, and pulled out my cock. I couldn't believe she was so willing, even with the lights still shining in from the side streets and businesses we were passing. But, after she had gotten me hard by hand, she leaned over and proceeded to give me head. After a bit, she came up, reminding me to let her know when I am about ready to cum, so she could get some Kleenex and catch it, so it wouldn't go all over. But, when I would warn her I was close, she would pull up, stop, and leave me hanging, until she felt it was time again to proceed. What I thought was kind of funny, was I told her we were coming up a-on traffic, and there were quite a few semis in the bunch, that would definitely be able to see what she was doing. Her reply was, “Oh well, maybe if they were getting head, they could keep their eyes on the road, instead of paying attention to what is going on with us,” than she went back down on me. Before I did get off, I tried and pre-warned her I was about ready to cum, and even tried to pull her up, but she decided she was going to take my cum in her mouth, instead. I guess I gave her a big load, because when she finally did come up, she told me I about drowned her, I had shot so much cum. I asked her why she broke her own rules, and she told me it was because I was the only guy that had treated her with so much respect while we were intimate, she felt she owed me something in return. Also, if I thought it was going to end here, I was definitely wrong. Anytime I was in the area of home, and my dad was not around, we would have our own get togethers.
Needless to say, that was only one weekend of the 4 weekends we spent together. Each time, I had to buy 2 boxes of condoms, and sometimes, I would have to make a trip back to the store to pick up another box. But on one weekend, we were trying a new position, and we were about half way thru with our love making, when nature called her. When I withdrew, I noticed I no longer had the condom on. She was afraid that something might have happened, and she started to reach inside her pussy with her fingers, but couldn't feel anything. In the meantime, I had checked the bed, and I hadn't found it either. The worse part, it was the last condom for that weekend. She finally told me to not worry about it, and we would finish up without it. Damn, that felt good to spray up, inside, without any restrictions. It also set off a surging, powerful orgasm within her, that it took almost 2 minutes to come down from. Afterwards, we were both praying with me cumming inside her, she wouldn't come up pregnant. 3 1/2 months later, when I was talking to her on the phone, telling her we had a job just 30 minutes from the house, she told me she had gotten pregnant, with twins, but miscarried a week before.
The next time we were down there working, instead of staying at the motel overnight, most nights she would come and get me, we go eat, go back to the house, but not every night did we make love. Most of the reason why, was because of my hours. I had to get up at 3am, take a shower, drive to the job site, do my daily inspections, get the truck ready, work all day until usually 10pm, than drive another hour back home. Even thou we didn't have sex every night, it was nice to be in her presence each night, sometimes she would sleep in my bed, sometimes she wouldn't.
But, on my weekends off, you're darn right we enjoyed our sex play. She even got to the point to where she would give me head to completion before sex, so I would last longer, and wake me up with a blow job. She was also curious about anal sex, so we tried it, and she found out she loved that, as well. So, she started off with this idea we could make love without a condom, and a few minutes before I am about ready to let loose, to pull out of her pussy and enter her ass, and cum in her ass. I had no problem with that, as long as she enjoyed it. But, what did freak me out, was the guys I worked with knew she was my step-mom, and on the first weekend off down there, she took me back to the motel, and when she went into the restroom, she apparently took off her undies. She knew I was a tit man, so she asked me if I had seen her new bra yet, as I was about ready to head out the door. I told her I hadn't, so she undid the top button and told me if I wanted to see it, I had to come over and unbutton her blouse, in order to see it. When I did, damn, it was a sexy, as all get out type of bra. I couldn't resist reaching down and feeling it, which led to reaching in and playing with her breast. From there it led to me pulling it down, so I could suck on her tit, and when I did that, she reached over and pulled my zipper down, pulled out my cock, and proceeded to give me head. When I was nice and stiff, she grabbed ahold of my cock and led me around to where I was up on the bed, between her legs, and guiding right into her wet pussy.
I told her we had to be quick, as my truck was out idling, and 2, I had to get to the loading site soon. So, we got a bit rowdy, and I told her I needed to pull out, as I didn't have a condom on, and I was about ready to cum. Instead, she wraps her legs around me, as well as her arms around my shoulders, and tells me to just let it go – we will deal with whatever may happen. So I did. I asked her if she really meant it, that WE would deal with whatever may happen, if she got pregnant. She told me that if her daughters weren't okay with it, than oh well, they are old enough to deal with their own things. And as for my dad, well, he has been neglecting his duties for all these years, and she didn't know exactly how much she needed sex, until we got together. So, he could deal with it, or file for a divorce, and we could both raise the c***d together – no matter what.
4 months later, she did notify me she was pregnant again. But this one, she mis-carried at a later time, and she was filled with regret. She asked me if I really wanted to keep our relationship going. I told her I did, and she told me she would have to figure out how we could. A year later, she died of heart complications. I still look back on what I had with her, and can't say, I have found anything to fill that void. She might have been my mother, step-mother, or my lover, but she was always that special woman to me.
My dad would drive out to her house (she lived out in the country, about a 30-minute drive from where we lived at in town), usually 2-3 a week, and we usually stayed late, with the 2 of them watching TV, and talking and stuff. On school nights, if we stayed out there late, I was told to go to sleep in the younger daughter's bedroom (Shannon.) Dawn had her own bedroom, which was much bigger, and less crowded, but I think they knew if I slept in there, I would try to work up the courage to make a move on her (Dawn,) not that she would ever go for it, as she was a goodie-to-shoe, all the time I knew her.
My dad and Lynn (step-mom) dated for a few years, before he moved down to live with my grandparents, while he worked in Wichita, Ks. Wichita was about 3 ½ hours away from where Lynn lived, but every other weekend, he would drive up and visit her, while I stayed with my grandparents. I kind of hated that, because I wanted to go, so I could possibly go horseback riding. He worked in Wichita for almost a year, before Lynn came down, and they rented a hotel room in Wichita. When they did, they also got a room for me, so I could go over there and go swimming, and be a bit free of parenting supervision.
During my time in the pool, a girl about my age was flirting with me, I at that time, I was all hip about myself, no shyness, ready to go for anything, no matter what. Anyways, we are splashing around in the pool, and playing around, when she submerged me, than followed after me, and kissed me under water. When we surfaced, I told her if she kept that up, she might be in trouble. She did this a few more times, with following up on the kisses. (I am not sure where her parents were, but I think they were on the opposite side of the pool, where they couldn't see us.) After about the 4th time, I decided if she was going to keep this up, than I am going to have a bit of fun, and see if I could feel her up. Not only did she let me, but she also pull the crotch over, so I could fully finger her. After about 15 minutes of this, she asked me to escort her up to their room, because she needed to get something. Hate to say, but we didn't do anything while in the room (I think I could have, if I would have just gone for the kiss, and feel.)
Fast forward 6 months, and that is when I found out that when Lynn was down visiting, her and dad had gotten married. Now, we were getting ready to move to Texas. Mind you, I had stayed late over at Lynn's, and even had some scolding from her, but never as a parent, and I had never had sisters before. The house they bought, and we moved into was a 4-bedroom, 2 car garage, with a gameroom above the garage. All of us k**s had bedrooms upstairs, while dad's and Lynn's bedroom was basically right at the foot of the stairs. So, if their door wasn't shut, you could basically see into the room, without much obstruction. And believe me, there were quite a few times I enjoyed that, as Lynn wouldn't have her bedroom door shut all the way while she was in her bra, or even braless, while I came downstairs.
At that time, I knew about sex, but had never gotten to 3rd base with any chick. Infact, I didn't hook up with anyone, until my Freshman Year JROTC Ball. And what made that night so special, was the girl I fucked, was already a good friend of mine, and was close with my best friend, and his twin brother. My best friend's twin brother, myself, and Sherrol were all in JROTC, therefore we all attended the ball that night. It was arranged with the parents, that my step-mom would pick up Brent, and Sherrol, and take us all to the ball, and Sherrol's mom would pick us up afterwards, and we would stay the night at her house (the ball wasn't to get over until 130am, and it was a Friday night, and with Brent's parents having to work the next day, and my step mom knowing she was going to be up late grading papers (She was a school teacher), she would want to sleep in.
At the ball, Sherrol and I were dancing, and stuff, and I just came out and asked her if she would like to be my girlfriend, which she replied, “I was hoping you would ask sometime, and was about ready to give up on waiting, but yes, I would love to be your girl.” We ended up breaking a few of the rules set forth by the school, and JROTC Colonel, but we didn't mind, since we didn't get caught. On the ride home, she asked that Brent and I ride in the back, so she could talk to her mom, which we agreed to (at this time, Brent didn't know I had asked her to be my girlfriend.) I guess on the way back to their house, Sherrol asked if it was okay if we screwed around that night, because once we got to the house, she told Sherrol that she and I could use her room that night, while Brent slept in Sherrol's bedroom, and she would sleep on the couch. Needless to say, Sherrol and I didn't get much sleep that night, and her mom never once interrupted us, nor made any comment on us making so much noise, the next morning. And Brent, well, I guess he was to beat, because he was none the wiser, until about a week later, when Sherrol and I went out, and did some cruising, before going to the lake and did some parking. We ended up being together until I got sent away to a boy's home, because of all the stuff I was doing, and how I was rebelling against school.
After I was emancipated, I moved back up to where my parents lived, and for a few weeks, stayed at their place, until I could get a job, and rent a place I could afford. During that time, I was sleeping downstairs, in the living room, on the couch. The only bathroom downstairs was adjoining to their bedroom, and had an entrance from both the hallway, and their bedroom. And as one knows, when one gets up, the first place to go is to hit to head and relieve themselves. A couple of times, unbeknownst to me, until I had opened the door, my step-mom would be standing there, usually topless, without a bra, and a few times, I even got to see her naked. I thought I had had fantasies about her before – when I had seen her tits, either covered in her bra, or uncovered, those compared nothing to these new ones.
Nothing happened, and I eventually moved away, but since I was always close in communication, and could open up to my step-mom about most things, I usually called her a couple times a month. When I moved out of state, that died down to once every few months, until I found out that she was having some health issues.
By this time, I was around 22 years old, and she was in her late 40's, I believe. I was on my second marriage, and it was not going that well, and I told her so, and we started speaking about why, and somehow, sex came up in the conversation (not sure if it was her, or me, that brought it up.) We discussed things like how I was getting flustered, because Della (my than wife) wasn't putting out, when I was home (I was an Over-the-road truck driver at that time, usually gone Sunday nights, until Friday late nights, sometimes Saturday mornings.) She told me about how my dad had been neglecting her needs, for a few years, and how she felt like she wasn't attractive anymore. I told her that was far from the truth, because if she and I weren't married, and I wasn't her step-son, I would be trying to hit on her so hard, she would barely know what had hit her, until the next morning, when she would wake up so sore from the screwing I had given her the night before.
We also talked about what parts we enjoyed in relationships, and even in sex. She told me that she couldn't give much of anyone an intimate kiss, because that was one of her hot zones, as well as kissing on the back of her neck, and nibbling on her ears. She also told me that she had a difficult time, when it came to having an orgasm, because no one knew how to hit any of her hot spots, like sucking on her tits when they were being intimate with her. Plus, she had never really had anyone perform foreplay on her, so she didn't know what all exactly was a build up to the intimacy, other than kissing. We got to where we were talking pretty freely about sexual things, that we enjoyed, or might enjoy, and might want to try – at some point in our lives.
After about a year and a half of all the talking, and my lead driver was on his vacation, I had a substitute lead driver, and we ended up having a pick up from south of where she lived, and we had to come thru her town, on the return home. So, I suggested to the lead, that we stop in and visit with her, and we could grab a bite to eat, at the same time, which he agreed to. So, I called her while we were still a few hours out, and told her we were planning on stopping in, and I wanted to visit with her, over dinner. She told me she would be happy to see me and let me know when we got to someplace close by to park. Well, I figured there was an old strip mall down the street from the house, and it would be easy for us to stick out to her, and we parked there, and I went to the station and called her. She came and got us, asked us what we were in the mood for, and we headed to Chili's. I introduced her to the other guy, told her he was a substitute lead driver, while my lead was on vacation. When we got to Chili's, she insisted we order whatever we wanted, she was going to get the tab (even thou I argued with her about it, almost the entire meal, she still wouldn't let me pay for it.) We spent an hour, maybe a little longer eating, talking, and catching up on a few things – than she took us back to the truck, as we really needed to get back on the road, as we had already stayed longer than what the company wanted us to allow for eating times. Since the truck had been shut off, and I had released all the air in the air tanks, I opened the doors, started the truck, so it could build air back up, and then went and told her good-bye. As I was leaving, I gave her a peck on the cheek, and started back for the truck. As I was about ready to climb in, she honked the horn, and motioned me back, and asked me what type of kiss was that. So, I leaned in, and was planning on giving her a peck on the lips, but she caught me by the neck, and started an intimate kiss. After a few minutes, she released me, and all I could say, was “Wow'. I leaned back in, and gave her another deep kiss, which she reciprocated, and when we broke, I told her I enjoyed that. She told me, that gives you something to look forward to, if we ever go any further. Needless to say, it was real fun trying to get back in the truck, hiding a woody from your co-driver – knowing your own step-mom gave you.
Fast forward a year, and I was driving for a different company, but this time, I not only drove a truck, but it was doing road resurfacing, and we went out of state to do jobs, as well as in state. In the time since I had visited my step-mom, we had talked more, and we had even discussed what it might be like, if we ever had time to ourselves, since I traveled without my wife, and my dad – like a dumb fool, even thou still married to, was living someplace else. I asked her, if she really would want me to come and visit, if I had the chance, which her reply was undoubtedly, Yes. So, I was in Oklahoma City, and the company works for 2 weeks straight, than on Friday afternoon, the company clocks out, and doesn't return until 10am Monday. Well, with me being only a few hours from Dallas, I called her and told her if she wanted, I had the gas money for round trip, plus some extra to do other things, if she wanted to come and get me. She told me to give her a few hours, so she could call my dad, and they would both come and get me. Hearing that, kind of sunk my expectations – which later, come to find out, it shouldn't have.
On the way back, dad, himself, told me that right now, he and Lynn were split up, and where he was staying, since he had roommates, they didn't have room for me, so I would have to stay with her. Than he proceeded to tell me had plans all weekend, and with his work schedule, he wouldn't be able to accompany us back to Oklahoma City. Otherwise, we just chatted about this and that, all the way back to Dallas. Lynn and I dropped off my dad at his place, and she asked if I minded if we stop at a little club in the neighborhood, which I replied no. We stopped, and she knew the bartender, and I asked him if he knew how to make a 57'Chevy, which he assured me, he did (needless to say, no, he didn't.) Lynn ordered her usual, a Strawberry Daqarie. She drank that one kind of fast, I thought, and we danced to a few songs, than she ordered another and downed that drink. When we were getting ready to leave, she asked me if I minded driving, and I told her I had better, with the way she downed her drinks.
Even thou I was raised in the Dallas area, and had known most of the area when I was a teen, this part of Dallas I didn't know, so she had to give me directions on how to get back to the Interstate. Along the way, she told me to pull into a 7-11 and get a couple of boxes of condoms in case we did do anything – since she was still capable of becoming pregnant. That kind of shocked me, knowing she was actually thinking about taking our talks to the next step.
Once we got back to the house, I opened the door, turned on the lights, and went back out for my overnight bag. She went in and asked me if I wanted a beer, or something to drink, which I replied tea was just fine. She went and got our drinks and went into the living room, and when I came back in, she told me to just set my bag down by the door, we will deal with it later, as she just wanted to sit and talk and catch up on what had been happening in my life. So, we both sat on the couch and talked for a little while, about this and that, when all of a sudden, she asked me, out of the blue, if I really did find her attractive. Of course, I couldn't lie to her, so I told her the truth – that if it wasn't for my dad, I would do about anything to hook up with her. She scooted closer to me, and replied that my dad wasn't there, so what was stopping me. So, I leaned over and started off with kissing her. I first gave her a sensual kiss on the lips, worked my way back to her ear, than her neck, and back to her mouth for a passionate kiss. I could tell by her breathing she was getting excited, and when she kissed me back, I could have sworn she was trying to rip my tongue from my mouth.
As she was wearing a skirt, and a button-down blouse, while I was still kissing her, I undid a few buttons and reached in and pulled one of her 42D sized tits from her bra and started to massage it. I worked it over from the base to the nipple, and even gave the nipple a few tweaks, making her gasp, each time I did. After I felt I had her plenty ways warmed up, I withdrew my hand and put it under her skirt and reached up for her panties. I got what I expected – drenched crotch. I pulled them aside, and played with her pussy for a bit, until she bit down on my lip and climaxed. Afterwards, she told me to keep those thoughts, while she went and got changed.
At the time I was visiting, she was living in one of the upstairs bedrooms, and the room she told me I was going to stay in was downstairs, right next to the front door. After about 10 minutes of waiting on her, I began to think she had changed her mind, and was getting up and getting ready to grab my bag and head to bed. Just as I got to my bag, she called my name, and I looked up to see her in an outstanding nightie. It was nothing super sexy, but to me, it made her body stand out more fuller, and drew out all her curves just right. She asked me where I thought I was going, and I simply told her that I was beginning to think she had changed her mind about things. Her reply was simple...”How could I, when you got me so worked up I creamed my pants, and am desperately needing the feel of a real cock.”
When she came back downstairs, she grabbed my hand and led me to the bedroom, and asked that I keep the light out, while she got disrobed, so I did. But, there is a street light almost right outside, and the blinds didn't do much to discourage any light, so I got to see plenty of her, and believe me, I liked what I saw. When she laid down on the bed, I started to get undressed, and afterwards crawled on the bed with her. I resumed kissing her, and got her worked up again, but inside of using my fingers anywhere on her body, I slowly made my way down her body with slow, wet kisses. I stopped and sucked on her tits, as well as nibbled on them, both seeming to bring deep grunted gasp from her. After paying attention to both her tits, I resumed my trip and worked my way down to her deliciously, wet pussy. She told me she wasn't really into oral foreplay, but I went ahead and started my bit on eating her up. For someone that wasn't into oral foreplay, she got off 3 times, before she begged me to stop, and to please make love to her.
When I crawled up, she asked me to be easy with entering her, as she hadn't had sex in over 6 years, so I tried to slowly enter her, but she was juiced up enough, it was easy to slide right on in. We made love in the missionary position for about ½ and hour, before I asked her if she would like to do it in any other position. She told me that the only other position she knew was on top, facing my feet, but she couldn't get off that way. So, I told her instead of facing my feet, turn and face me, while on top, and we would remedy her not getting off while being on top. She slowly lowered herself on me, and when she reached the base, that was when she realized, I was the biggest cock she had ever had. I was actually topping out against her cervix, and according to her, it wasn't painful, instead, it was highly erotic, and made her feel more delighted.
She rode me, at her own pace for about 15 minutes, when she cursed that she would get right to the edge of building up a climax, and than it would just fall flat out. I told her the next time she got that high feeling, let me know, and let me take over her movements, and how she is positioned in leaning. The next time she got to the edge of a pending build up, she told me, so I grabbed her ass, and one hand on her back, and leaned her forward some, and picked up the pace of the stroking. Within a few minutes, I could hear her building up to a delightful cum, and I could also tell, she wasn't a gasper, or a clincher, but she was a screamer. And believe me when I tell you, when she got off, if anyone else had been in that house, they would have known she just came, like her life depended on it. I was surprised even, that the neighbors didn't hear her.
We kept at it, off and on, most of the night. If I got soft in between, during our breaks, she would give me a hand job to get me back up. But, we finally finished around 5 in the morning.
When I woke up, around 8:30, she had already gotten up, taken a shower, and was making breakfast for us. She wanted to go ahead and keep my original plans of an excuse to come down, so we got ready and went to the amusement park, and spent the day. Instead of going home and fixing something to eat, I decided it was my turn to treat for dinner, and it was up to her to pick a spot – I told her not to worry about the cost, as I was prepared to spend whatever on her for the weekend. She picked a nice 4 star restaurant, and we had a few drinks with our dinner, and laughed about a few things that we had done that day. Also discussed when I had to be back, if we regretted the night before, and if not, would we want to repeat the episode. I told her I had no regrets, and most definitely, I would love to repeat it, as many times, and whenever we could. After dinner, we headed home, and we decided that the previous night was just not enough, and that we would spend the night together, again.
When we were getting ready for bed, I asked her if she would mind giving me head, which she told me she didn't mind giving head, in fact, she enjoyed it, but she couldn't handle someone cumming in her mouth, or the taste of it. So, she started giving me head, and boy, could that woman give head. After only a few minutes, I had to tell her to back off, otherwise she would get a mouth full, so she did. That night was also the first night she was introduced to a few new positions, as she had told me earlier that the only 2 positions she had ever tried was missionary and reverse cowgirl. She found out that she liked doggie-style the most, and also that she was a squirter. When she came that night, she came so hard, so many times, we had to take the mattress out afterwards and let it air out and dry. So, that night I ended up sleeping upstairs, in her bed. I definitely loved snuggling up and spooning with her all that morning.
The next day, we ran a few errands, and I got some items I had been wanting to get for a while, since I didn't visit Texas much, and had to do some chores and my laundry. Let's just say, she made sure ALL my laundry was washed, before we left to go back to Oklahoma City. She even offered to come upstairs to the shower, and wash me, but would not join me in the shower. I did my darnest to get her in, but n matter how hard I tried, she refused. That night, we didn't do anything, as we had to leave at midnight, so I could get back to the job site on time the next morning. But, she offered to give me head, on the way, if I didn't allow others to see what she was doing. I couldn't turn that down.
We left at midnight, and shortly after we got out of the burbs of Dallas, she reached over and undid my pants, and pulled out my cock. I couldn't believe she was so willing, even with the lights still shining in from the side streets and businesses we were passing. But, after she had gotten me hard by hand, she leaned over and proceeded to give me head. After a bit, she came up, reminding me to let her know when I am about ready to cum, so she could get some Kleenex and catch it, so it wouldn't go all over. But, when I would warn her I was close, she would pull up, stop, and leave me hanging, until she felt it was time again to proceed. What I thought was kind of funny, was I told her we were coming up a-on traffic, and there were quite a few semis in the bunch, that would definitely be able to see what she was doing. Her reply was, “Oh well, maybe if they were getting head, they could keep their eyes on the road, instead of paying attention to what is going on with us,” than she went back down on me. Before I did get off, I tried and pre-warned her I was about ready to cum, and even tried to pull her up, but she decided she was going to take my cum in her mouth, instead. I guess I gave her a big load, because when she finally did come up, she told me I about drowned her, I had shot so much cum. I asked her why she broke her own rules, and she told me it was because I was the only guy that had treated her with so much respect while we were intimate, she felt she owed me something in return. Also, if I thought it was going to end here, I was definitely wrong. Anytime I was in the area of home, and my dad was not around, we would have our own get togethers.
Needless to say, that was only one weekend of the 4 weekends we spent together. Each time, I had to buy 2 boxes of condoms, and sometimes, I would have to make a trip back to the store to pick up another box. But on one weekend, we were trying a new position, and we were about half way thru with our love making, when nature called her. When I withdrew, I noticed I no longer had the condom on. She was afraid that something might have happened, and she started to reach inside her pussy with her fingers, but couldn't feel anything. In the meantime, I had checked the bed, and I hadn't found it either. The worse part, it was the last condom for that weekend. She finally told me to not worry about it, and we would finish up without it. Damn, that felt good to spray up, inside, without any restrictions. It also set off a surging, powerful orgasm within her, that it took almost 2 minutes to come down from. Afterwards, we were both praying with me cumming inside her, she wouldn't come up pregnant. 3 1/2 months later, when I was talking to her on the phone, telling her we had a job just 30 minutes from the house, she told me she had gotten pregnant, with twins, but miscarried a week before.
The next time we were down there working, instead of staying at the motel overnight, most nights she would come and get me, we go eat, go back to the house, but not every night did we make love. Most of the reason why, was because of my hours. I had to get up at 3am, take a shower, drive to the job site, do my daily inspections, get the truck ready, work all day until usually 10pm, than drive another hour back home. Even thou we didn't have sex every night, it was nice to be in her presence each night, sometimes she would sleep in my bed, sometimes she wouldn't.
But, on my weekends off, you're darn right we enjoyed our sex play. She even got to the point to where she would give me head to completion before sex, so I would last longer, and wake me up with a blow job. She was also curious about anal sex, so we tried it, and she found out she loved that, as well. So, she started off with this idea we could make love without a condom, and a few minutes before I am about ready to let loose, to pull out of her pussy and enter her ass, and cum in her ass. I had no problem with that, as long as she enjoyed it. But, what did freak me out, was the guys I worked with knew she was my step-mom, and on the first weekend off down there, she took me back to the motel, and when she went into the restroom, she apparently took off her undies. She knew I was a tit man, so she asked me if I had seen her new bra yet, as I was about ready to head out the door. I told her I hadn't, so she undid the top button and told me if I wanted to see it, I had to come over and unbutton her blouse, in order to see it. When I did, damn, it was a sexy, as all get out type of bra. I couldn't resist reaching down and feeling it, which led to reaching in and playing with her breast. From there it led to me pulling it down, so I could suck on her tit, and when I did that, she reached over and pulled my zipper down, pulled out my cock, and proceeded to give me head. When I was nice and stiff, she grabbed ahold of my cock and led me around to where I was up on the bed, between her legs, and guiding right into her wet pussy.
I told her we had to be quick, as my truck was out idling, and 2, I had to get to the loading site soon. So, we got a bit rowdy, and I told her I needed to pull out, as I didn't have a condom on, and I was about ready to cum. Instead, she wraps her legs around me, as well as her arms around my shoulders, and tells me to just let it go – we will deal with whatever may happen. So I did. I asked her if she really meant it, that WE would deal with whatever may happen, if she got pregnant. She told me that if her daughters weren't okay with it, than oh well, they are old enough to deal with their own things. And as for my dad, well, he has been neglecting his duties for all these years, and she didn't know exactly how much she needed sex, until we got together. So, he could deal with it, or file for a divorce, and we could both raise the c***d together – no matter what.
4 months later, she did notify me she was pregnant again. But this one, she mis-carried at a later time, and she was filled with regret. She asked me if I really wanted to keep our relationship going. I told her I did, and she told me she would have to figure out how we could. A year later, she died of heart complications. I still look back on what I had with her, and can't say, I have found anything to fill that void. She might have been my mother, step-mother, or my lover, but she was always that special woman to me.
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