An Older Woman

AN OLDER WOMAN

I realized the other day I hadn’t written a story in a while while I was talking to somebody about living in San Diego. Again, like my other stories, this is a true story.

I had been stationed in San Diego for a while now and had several exciting sexual adventures. I wrote about one that included me and a couple in Del Mar. As with my adventure with the couple, I was living with my girlfriend in the La Jolla area. She was fun, but I always seemed to be looking for more.

I was gassing my car at the Shell station at UTC one day and noticed this attractive, older woman gassing her BMW next to me. She looked at me and smiled so I smiled back. When she finished putting gas in her car, she came over to me and told me I looked like Campbell Scott. For those of you that don’t know who that is, he is the son of George C Scott and he has done several movies. I asked her if that was a good thing, and she said it was a very good thing. I thanked her and told her she was a very beautiful woman herself. She asked me if I was busy (and of course I said no), and if I would like to go to the McDonalds next to the gas station for a cup of coffee. I wasn’t much of a coffee drinker, but I told her I would gladly join her. I ended up getting a diet coke instead.

We sat and chatted for about an hour. She was 50 years old (I was only 26 at the time) and divorced. All 3 of her kids were older and moved out and she was able to live in a very nice home in Encinitas, along the cliff line, because she received a nice alimony check every month from her ex husband. She also sold real estate which brought in a nice chunk of change for her too. I talked about growing up in Kentucky, and being in the Navy. I talked about everything, but my live in girlfriend. We got along really well and it had to be the nicest hour long conversation I had ever had. She had to leave to go to a house showing, and I had to get back home. As we stood up, she asked me if I was busy the next Friday and if I would like to have dinner at her house. I knew my girlfriend had to work so I got directions to her house and told her I would be there at 7. I also told my girlfriend that I was going out with the guys and I would be home late. She said she would go out with the girls after work. Everything seemed to be fitting into place.

The ship I was on got underway on Monday morning and got back on Friday. Luckily while the ship was underway, I was always really busy, which made the week go by pretty quickly. All I could think about all week long though was how good looking the older woman was. I always had a thing for older women. I wrote about a couple other adventures, from when I was younger, with older women. Now that I was older, I was a little more worldly, and more open minded about a lot of things. I felt like an old pro compared to when I was a teenager. The ship pulled in kind of early at about 2 pm and we all got the rest of the day off because we had been at sea all week long. I was excited because of my date that evening, and because it was my “virgin weekend”. That meant I didn’t have duty the entire weekend. I hurried home because I was so excited and was met very warmly by my girlfriend. She didn’t have to be at work until 5 so we spent all of her available time in the sack. We both had a lot of sexual energy to burn after being apart all week. I was a little worried about burning too much of my energy, but I was only 26 so I had a lot of energy to spare. We even did it once in the shower while she was trying to get ready for work.

She finally finshed getting dressed for work, and headed out. I followed her down and had a bite to eat in La Jolla next to where she worked. I didn’t eat too much because dinner was coming, but I did had to eat something because I was famished. I got back to the apartment at 6, cleaned up a little bit and headed out at about 6:20. I hoped traffic wouldn’t be too bad and I must have gotten very, very lucky because it was moving very smoothly north of my apartment. As usual, I got to her place a little early after looking for it a little while. I noticed it right away once I got on her street because the house was huge and I recognized her car in the driveway. I didn’t want to appear to anxious so I waited at the end of her block for a little bit and then pulled into her driveway a little after 7. She must have expected I would be late because of the traffic and being a little late didn’t seem to bother her at all. She opened the door to let me in and gave me a big hug and kiss on the cheek like people from California tended to do. All I could think about during the hug was how great she smelled, and how firm her boobs were. She seemed to be squeezing me harder than normal purposely so I could feel her tits. She was very successful. She offered me a glass of wine and asked me to go on the back patio with her. She said she had made spaghetti and the sauce was on the stove just waiting to be served. We walked on the back patio which was fantastic. Even though it was dark, you could still see down the coast all the way to La Jolla. You could also feel the breeze blowing on you. For those of you that have not been to Southern California, the evenings can get pretty cool so the breeze I was enjoying was pretty cool that night. Maybe she planned it that way because as we were chatting and drinking our wine, she snuggled next to me and asked if she could stand there like that to stay warm. Of course since I was a gentleman, I quickly said she could so she wrapped her arm around mine and we stood there drinking and chatting. We were outside for two drinks (two for her, three for me) and then decided it was time to eat. I was glad I had snacked earlier. She poured some red wine in the glasses on the table and then brought out and served the spaghetti with a salad. The meal was great, the conversation was fun, and the more wine was fantastic. We finally finished eating and then went into her fantastic living room to talk some more with a glass of wine for each of us. I sat on the loveseat and she turned on some music, and started a fire. The fire felt great because the living room opened up onto the patio and the screen door was open letting in the cool, crisp night air. Maybe she had planned it that way because she sat down on the love seat next to me and then asked if it was ok to cover ourselves with a blanket to help stay warm. We talked some more and just as I thought that’s all we were going to do, she reached over and kissed me. I guess she thought I wasn’t going to make the first move. I found out differently.

The kiss was a good one. She skillfully probed my mouth with her tongue, and also used her hands all over my body. The way she was rubbing her hands on my chest, it seemed like a teenage boy trying to get some tit action. I had on a button down shirt with my shorts, that she somehow managed to unbutton as she was kissing me. Her hands were still a little cold from holding her glass of wine and they made my nipples harden as she rubbed across them. She felt my nipples hardness and began pinching them a little hard. I yelped once and she pulled back to ask me if it hurt, and I said no so she just smiled. Now that our lips were unlocked, she stood up and walked over to close the sliding door. I sat there and waited for her and took another sip of my wine. When she returned, she didn’t sit back down on the love seat, but sat on my lap, facing me. She unbuttoned my shirt all the way down to my navel and put both of her hands inside my shirt. She began tweeking both of my nipples as she leaned over and kissed me again. It felt fantastic. She then pulled away from my lips and started kissing my cheek on the way to my ear and my neck. I just sat back and enjoyed every moment of it. As she was nibbling on my ear and neck, she pulled one of her hands from my shirt and worked her hand down towards my cock. She was kissing my neck, rubbing my nipple, and groping my crotch as she sat on top of me as if I was the woman and she was the man. Now I know why girls liked it so much. She asked me if I liked that and I could barely speak, but I got the word “Yes” out of my mouth finally. She must have liked that answer because she squeezed my cock even harder. She asked me if I really liked it, and I repeated my answer again. She stood up and told me to follow her.

She grabbed my hand and led me down the hallway to her room. Once we got there, she told me to lay on the bed while she changed into something else. Since she didn’t tell me to get undressed, I only pulled my shirt tail out of my shorts, and laid on the bed. I looked around the nicely decorated room and noticed she had some exquisite tastes. It wasn’t too long before she came out of the bathroom and totally surprised me. She was wearing a man’s button down shirt with a tie loosely around her neck, and a hat on her head with her hair pulled up under the hat. It looked pretty cool. She asked me if I liked it and if she looked like a man. Even though I knew she was a woman, I did have to admit, she looked a little manly wearing those clothes. It was pretty sexy. She asked me how much I liked it and what I would do to see her out of the clothes. I told her I would do anything. She just smiled and went back into the bathroom. All kinds of thoughts were running through my mind while she was in there about what she had in mind. I didn’t have to wait long because she came out of the bathroom and surprised me even more. Now she had men’s pants on with her shirt tucked in and a little moustache on her face. She also had a bag of something that I didn’t know was in there. She told me to stand up and walked over to me and kissed me. It felt a little strange with her moustache but it was also very exciting. As I was kissing her, I started to reach up to fill her tits and she just smacked my hand away and said “not now”. She kissed me again and then pushed away from me. She gave me the bag and told me to open it. I looked inside and it was full of women’s clothes. I asked her what they were and she said they were for me. I reached inside and pulled out a short dress, a pair of what turned out to be stockings (not pantyhose), and a nice pair of lacy, thong panties. At the bottom of the bag was a large, dark wig.

I asked her if she really wanted me to put those things on, and she said yes, that if I was willing to do anything, I should put them on. I did remember saying that and I was so extremely turned on, I was willing to do anything that night. As I began taking my own clothes off, she just stepped back and watched. My shirt was already unbuttoned and hanging out, so that came off easily. I had taken my shoes off at the door which left my shorts and my boxer briefs. I pulled my shorts down and she just eyed my now hard, 8” cock. I took my briefs off and threw my stuff on the nightstand. I reached over on the bed and picked up the panties. I slipped them on and they seemed to fit perfectly. I asked her how she did that, and she said she sized me up that day at McDonalds. Then I sat down on the bed and picked up the stockings she had bought. She told me the seams went up the back of my legs. The stockings had a nice elastic top that I slipped up my leg, being careful to keep the seam on the back of the my leg. She had to tell me how to work them up my leg so they would reach my thigh so that I would do it without putting a run in them. It was a slow process, but I finally got my right stocking on. It looked kind of funny because of my hairy legs, but the white stockings looked cool because they matched my white panties. They felt fantastic. I reached over and grabbed the stocking for my left leg and was able to slip that on pretty quickly this time. I stood up and looked at myself in the mirror and it was pretty sexy. She was just smiling. I picked up the dress to put on and she asked me again if I knew how to put it on. I thought I just stepped into the dress, and she told me it was easier to slip it over my head. I slipped it over my head and again it fit perfectly. I was amazed that she was able to do that. I pulled the straps on my shoulder and smoothed out the dress. I stood up and again saw myself in the mirror. It was a strange transformation. I sat back down on the bed where I could see myself in the mirror and put the wig on. It wasn’t that hard. She did have to even it out, but she didn’t have to adjust it that much. Then she reached into her pocket and pulled out a tube of lipstick. She told me not to worry, because she would put it on for me. It was a bright red color that matched the red dress very well. Now she told me to stand up and put the high heels on. They were the biggest pair of high heels I had ever seen and she said they were hard to find, but she found them. I put them on and just about fell down, so she grabbed me and helped me gain my balance. She told me to stand still while she walked into the bathroom and brought out a little footstool. I didn’t know what it was for, but realized she needed it to even our heights. Finally, she stood on the stool in front of me, and began kissing me.

Because of the high heels, I was still a little taller than her, but she didn’t seem to care. She held my face with her hands and kissed me softly, then very hard. She began nibbling on my ear again, and even bit my neck a little. Her hands were fondling my chest again until she slipped the straps on the dress off my shoulders. She pulled the dress down a little exposing my nipples. She kissed down from my neck to my nipples and began nibbling on them. Her nibbles included bites which were a little painful, but also very stimulating. She stepped down off the stool, which made her a lot shorter than me, but put her mouth about chest level. She nibbled and sucked on each one of my nipples and moved her hands down my body. She held me tight in her arms with her hands on my ass. She squeezed my cheeks and rubbed a finger on the crack of my ass. I was really getting turned on. She moved her hands down to the bottom of the dress and pulled it up a little exposing the cheeks of my ass. She caressed my ass with her left hand and moved her right hand around to my cock. The front of the panty didn’t cover my cock that well and she rubbed my the tip of my cock that stuck up over the top of the panties. While she was doing that, she used her left hand to pull the string of my thong out of the crack of my ass. She was just rubbing the crack of my ass with one hand and stroking my cock with the other. I didn’t think I was going to be able to take it any longer. That’s when she stopped. She pushed me back on the bed and made me lean back.

I felt like such a slut at that point (which I loved). I was leaning back with a dress bunched up around my waist, stockings on my legs with high heels on my feet, and a woman (that looked like a man) between my legs. She was between there nibbling on my thighs, and just licking on the tip of my cock as it stood up over the panties. I desperately wanted her to take my entire cock into her mouth. She began licking at the front of the panties and my cock as if they were a pussy. It felt great and I didn’t want her to stop (except to take my entire cock into her mouth), but she stopped and told me to turn over on my stomach. I did that and was still laying on the bed with my feet on the floor and she pulled the string of the thong aside and began licking my ass. She licked it with the width of her tongue, and probed it with the tip of her tongue. She must have done it before because she was able to get quite a bit of her tongue into the crack of my ass. That felt great too. She stopped to tell me to turn back over and then asked me if I liked her licking my pussy. I told her it felt fantastic, and she told me that now I had to take care of her. I was looking forward to that because I love licking pussy!

She stood up and then called me a slut. I told her I was a slut and for her to use me. I kind of got the feeling that is where she was going with the role playing. She then kicked off her loafers and unsnapped her pants. That really turned me on. I was looking forward for her to pulling her pants down and showing my a moist, shaven pussy. She slipped her pants off and even had boxers on under them. When she pulled her boxers down, she really surprised me. Under them, she was wearing a large, strap on dildo. She asked me if I liked her cock and I told her I loved it. She told me if I liked it so much, to suck it and then climbed on the bed, straddling my chest. I grabbed the dildo with both hands and began sucking it as well as I could. It really must have turned her on, because she was moaning as I slobbered on her cock. I sucked on it for a few minutes and I even think she came and then she told me to stop. At that point I didn’t know what she had in mind. She walked into the bathroom and came out with a towel and then layed it on the bed. She told me to lay back on the pillows so my ass was on the towel. As I was doing that, she reached into her nightstand and got out a tube of something. I didn’t know what it was then, but now it would be pretty evident to me. She climbed on the bed, between my legs and slipped my panties off me. She sniffed the crotch and licked it to get all of my precum off. Now I layed there like a total slut with no panties, a big hard on, a dress bunched up around my waist and a woman with a big cock between my legs. She opened the tube and squirted a clear liquid onto her fingers. She began rubbing it onto the dildo until it was really well covered. She then squirted a little more onto her fingers, reached between my legs and began rubbing it on the crack of my ass. It was cold, but it felt great. She got a little more from the tube, rubbed it onto her fingers and then stuck her fingers in my ass. The entire time, she kept calling me her little slut. It was such a turn on.

After she closed up the tube, she inched up between my legs some more and said I was her little slut, and I needed fucked. Now I knew exactly what she had in mind. LOL. I didn’t know if I could handle her big dildo, but I played along with her and told her I did need fucked. She reached down and grabbed her cock with her right hand and told me to pick my feet up and put them on her shoulders. She aimed the cock at the crack of my ass and began stabbing at it. She was just teasing me. When she stopped teasing she rubbed the tip of the cock up and down the crack of my ass until she hit the right spot. With her left hand on my leg, she held her dildo steady and began pushing. It was right on target, because it started going right into my ass. She was in charge, but she knew it was going to hurt, so she just looked at me and told me she wasn’t going to hurt me and to relax. She eased the tip in and just held it there after it entered. It hurt like hell at first, but luckily she had really covered it in lube and put even more lube in my ass. When she sensed it wasn’t hurting any more, she pushed it in some more which seemed painless. Each time she would push it some more, she would inch forward more on her knees. After some time, she eventually got the entire thing into my ass. It felt pretty good. She took her right hand off the cock and put it on my left leg so that she was holding my feet in the air and she began moving her hips back and forth. The cock started moving in and out of my ass. I felt like a slut being fucked like that and she kept calling me her slut and a whore. She fucked me like that for a few minutes and then pulled the cock all the way out. She told me to get up and she took my place on the bed with her lap on the towel. She was laying on her back with her cock standing straight up with a couple of buttons undone on her shirt now. I was standing on the floor in my stockings and heels still, with a dress bundled around me. She told me to climb on the bed and straddle her. I thought she was going to suck my cock at that point, but once I got there, she pushed me back a little so that the cock was pushing at the crack of my ass again. I knew what she wanted so I raised up a little, reached around to hold the cock and guided it into my ass. It was a lot easier this time. After I sat all the way down on the cock, she told me to play with my nipples as she put her hands on my hips. She told me to pinch my nipples while I bounced up and down. I was bouncing and she seemed to be bouncing me with her hands. It was a great feeling as the dildo was pushing on my prostate gland. I was so turned on! My cock was as hard as ever and sticking straight out and I was about to cum. I told her I was about to cum any minute now which seemed to thrill her. I moved my hands down to the cheeks of my ass and she moved her hands up to my nipples. A little of the lube from my ass got on my right hand as I bounced up and down. I moved my right hand and began stroking my cock with the lube. I told her I was about to cum and she told me to shoot it now. That’s all it took. Between the night of role playing to that point, the gorgeous woman under me, and the dildo pushing on my prostate, I shot one of the biggest loads I had ever shot in my life. Most of it hit her in the face, and some of it got on her tie. I was so tender and my dick kept twitching. I waited for it to stop, and while I was doing that, she had reached under her strap on and was rubbing her clit. She came in about 1 minute. At that point we both just sat still for a moment, until the orgasms had stopped. It felt fantastic. When she stopped cumming, she asked me what I was doing and told me to kiss her. I gave her a big, sloppy kiss, and tasted some of my own cum on her lips. It was strange but good. I started to just lay down next to her and hold her, but she asked me what I was doing. She told me to lick the rest of the cum from her face like the slut that I was would do. I eagerly obeyed her and then layed down. I think we both needed the rest. It was probably some of the best sex I had ever had and I didn’t want to go home. We talked about it and she said I could stay so I called home and said I was crashing at my friends house because we all drank too much. Then I proceeded to have one of the funnest nights I had ever, or will ever, had.