Ellen and I caught each other on the rebound. We met when we both lived in a Caribbean resort area. After a nasty break up, I’d had 3-4 very unpleasant months of scrambling for a place to live, anonymous 1-night stands, way too much drinking and drugs, and more than a few times going home with some woman just for a place to sleep. This finally ended when I moved into a small apartment on the first floor of Ellen’s house. She lived in the top floor.
She’d had a recent breakup, too. A few years before this, her marriage of about 30yrs had ended abruptly. This made me realize my problems weren’t quite so awful. I was about to turn 26 when we met. She was obviously much older, though she liked to be coy about her age. I worked out on my own that she was 53yrs old.
If anyone had asked me, I’d have said she was completely out of my league. She was smart, interesting to talk with, and wealthy. She was also one of those lucky people who both look their age and look fantastic. She wasn’t pretty, but very good-looking anyways (a combination I’ve always liked), with a fantastic slim body, a super-sexy older woman. We talked a lot sitting on the porch or while she was working in her flower bed. She was wry, cheerful, and interesting. But believing her out of reach, not wanting to screw up a great living situation, and remembering that she was older than my mother, I dismissed the idea of the two of us having sex from my mind. I thoroughly enjoyed looking at her, though.
Living there was great. It was quiet, and a short walk from a great beach. It was a relief to go to a place of my own after work. I got into a good routine–get up, exercise, walk back to the house, relax, go to work around noon. I cut out almost all the partying and made a conscious decision to do without female company for a while. I might have an after work beer, but mostly I just went back home and read my book.
One morning I returned from a swim. She was almost always outside in the morning, but wasn’t this particular time. After taking a shower, I decided to take a few minutes and grant myself an orgasm. So I got on the pull-out bed in my apartment, leaned back on the pillows, and got to it. Right in the middle of this, I looked up and saw Ellen standing and looking at me. In each hand she held a frozen chicken, a sight I still remember vividly.
My apartment didn’t have a locking door of its own, it was behind a locking gate that secured the whole house. Ellen had asked me if she could keep a few things in my freezer for a day or two. She hadn’t seen me come back from the beach, so she just walked in, grabbed the two chickens out of the freezer, heard something, took a look, and there I was.
I was about 80% of the way through the process. For whatever reason, I didn’t even flinch, I just looked her in the face and kept going. And she stood there with those two chickens and watched till the end. We looked each other in the face as I stroked my dick and kneaded my balls until my head rocked back when I came. We looked at each other again for a minute, then she walked out without saying a word. A pretty weird experience. I was embarrassed, but I also sorta liked it.
She stayed inside her place the rest of the morning till I left for work, which was unusual. She didn’t step out and give me a wave when I got back that night, which was also unusual. And I didn’t see her at all the next day or night, which was extremely unusual. This made me feel bad. It hadn’t bothered me that much, but she was obviously embarrassed. I didn’t want her to feel like she had to hide whenever I was there, so I decided that if I didn’t see her the next time I came back from the beach, I’d knock on her door to try and make it better.
When I returned from the beach next morning, she was sitting in porch chair right outside the door to my place. I am so, so sorry, she said as I walked up, I intruded on your privacy, that was wrong of me, I’m so sorry, that’s your house, I shouldn’t have done that. Listen, I said, these things happen, it was just an accident, I’m fine, no problem. We went back and forth like this and it sorta escalated. No, no, she said, I did something terrible, I was in your house without permission, that was awful. No, really, I said, it was no big deal, it didn’t bother me at all, it’s nothing to get upset about.
This went on long enough that I got slightly annoyed. She was a bit over the top with the apologies. Look, I finally said, it was obviously no problem for either of us. I kept going and enjoyed myself just fine, and you stayed for the whole thing, so you must have found it interesting. She was about to say something as she sat in the chair. Then her eyes dropped to my body and she gave a little gasp. I looked down and realized that I had an obvious and growing bulge in my shorts. Huh, I said, looking at her, then I shrugged my shoulders, gestured that she should follow me, then went into my place, leaving the door open. As I took my shorts and shirt off, she came in behind me. Have a seat, I said as my dick finished getting hard.
She sat a chair across from the bed, legs crossed and hands folded in her lap. I sat on the corner of the bed and spread my legs wide to give her the best view and started stroking my dick, trying to put on a little show for her, playing with my balls and running my finger around the head, taking my time. She sat there calmly, not saying anything, but her shifting around in her seat and biting and licking her lips soon made it clear that she found this mighty interesting. I slowed down a couple times when I was about to cum to make it last, then stroked myself to an excellent orgasm. She sat for a few more, just looking at me, then got up and left. Not sure why I chose to do this–when she followed me in, I could easily have gotten her to fuck, I’m sure.
When I went to leave for work a while later, she was in her flower bed. We got chatty for a bit before I left, just as we usually did. She was even more cheery than normal, almost as if nothing had happened, but not quite. As I drove to work, I wasn’t sure how this would work out, but I knew I liked it so far.
She was waiting for me outside my door again as I returned from the beach the next morning. I started getting hard as I walked up to her, gave her a grin, and went into my place, leaving the door open. I pulled my clothes off as I walked in, then turned to face her, my dick hard. She looked me up and down and I let her. Tell me what to do, she said in a very calm voice. Tell me what to do, she said again, tell me what to do. I sat down on the corner of the bed, leaned back, and spread my legs. Get on your knees and suck my dick, I said. This had taken an interesting turn–I was ordering this super-sexy much older woman who was out of my league to suck my dick and she was going to do it. My heart was pounding and I was dry-mouthed and breathing hard.
She looked up at me from her knees with my dick in her hand. Tell me what to do, she said again, tell me what to do. Lick it, I said, lick it and get it wet, lick the head, stroke it, suck the head, suck my balls. I was moaning and grunting in pleasure. Tell me what to do, she kept saying. Go easy for a bit, I said a couple times, slow down and make it last, I wanna enjoy this. She did as I said and sucked my dick for a good long time, moaning and looking up at me constantly. This was so hot it was almost surreal–this fantastic woman was on her knees with my dick in her mouth, cupping my balls in her hand, looking up at me for instructions, and doing whatever I said. I started rocking my hips, and thrusting a little. Suck it deep, I said, I’m gonna cum, take it all the way in and suck while I cum, swallow it all. She moaned as she did this, which made me start cumming. I came as hard as I ever have, long and hard and lots of cum, so hard I saw stars.
After I got my shit together, I looked down at her. She was still on her knees, sucking my dick lightly. She picked her head up and looked at me. She’d not been able to swallow it all and had cum all around her mouth. I pulled her up to me and kissed her (the most interesting first kiss I’ve ever had), licking the cum off her face as I did. I got some cum on my face and she licked that off. Then I stood her up and pushed her back and against the wall as we continued kissing. She wrapped her legs around one of my thighs and ground her pussy into it hard through the linen pants she was wearing, her feet barely touching the ground as I held her ass in both hands, pulling her pussy into my leg, and we had a nice, wet, make-out session.
After a bit of this, she pulled her head back and looked at me while continuing to grind her pussy on my thigh. I think I’m going to have an orgasm, she said in a very matter-of-fact voice, like she was telling me she was going to the store or something, I think I’m going to have a really big orgasm. Having her tell me this so calmly while she frantically humped my leg was strange but weirdly hot. All of a sudden she pulled me into her by the neck, strongly hugged herself to me, and rode my thigh slow and super hard, shuddering as she did, her abs and thighs and ass flexing hard, crying out into my ear, cumming really hard and really long.
When that finished, we started kissing again while she continued slowly grinding her pussy into me. Soon, she stopped kissing me and looked at me again while still grinding on my leg. Well, she said in that same matter-of-fact voice, I think I’m going to have another orgasm. Then she did, this time throwing her head back with oh oh oh oh oh as she came.
My dick was hard again and she reached down and wrapped her hand around it. I backed away from her and sat down again on the corner of the bed with my legs spread and my dick straight up. I didn’t wait for her to ask me to tell her what to do this time. Get back on your knees and suck my dick again, I said, suck it, lick the head, squeeze my balls. It was incredible to have this woman on her knees sucking my dick and so obviously loving it. I’m gonna cum, I said, and she sucked the cum out of me just as I told her to last time.
After I came and we were done, she stood up. She usually took care with her appearance–nice clothes, neatly dressed, hair neat. Not now. Her light-colored linen pants were pulled down low and soaked at the crotch. Her blouse was pulled to one side and wet with sweat and cum. And her hair was a mess. As she stood there, a smile slowly grew on her face, eventually becoming big, broad, and very naughty looking. I found this really cool, about as cool as the excellent dick-sucking and the rest of it, believe it or not. I smiled right back at her. She left without saying a word. A bit later, we were chatting away outside, as we normally did, no indication of our little encounter, except that we both had big, goofy smiles on our faces.
This was only the beginning of what became several months of intense, kinky fucking and sucking. We experimented with all kinds of stuff–bondage, heavy spanking, really rough sex, and even fucking while other people watched. It was incredible. She once joked that it was like one of those student and high school teacher things. I said it was more like a student and dean of the college thing. And we became close friends. It was one of the best experiences of my life.
Source: reddit.com/r/gonewildstories/comments/r7kh0n/i_order_a_fantastic_sexy_woman_twice_my_age_and
How fantastic for both of you!
Older women can be magic sex partners. You are so lucky to have had that experience.
How did it end?