This is chapter 1.
When I deflowered Jayne she was the oldest virgin I have ever fucked. When I took her virginity she was 85 years old.
As mentioned in the previous story about Emily and I, Jayne is an 85 year old virgin with a slim build, good size tits, and wears mumu dresses all the time with nothing under them. She was sheltered and repressed from having sex with boys or men while growing up because of her mother’s attitude toward it. She never married and has never been with a man sexually.
Here is what Emily filled me in on about Jayne, the back story:
Up until 30 years ago when she was finally able to move out of her mother’s place she never masturbated. That is when she moved into the apartment building she is in now. She discovered the joy of self pleasure especially with sex toys she has purchased. But her mother, in an effort to keep apparent control of her, had her lesbian aunt move into the same apartment building. Despite this Jayne still masturbated with sex toys such as dildo’s, etc. Something her mother never would have approved of. In fact Jayne had to rent a storage cage in the apartment building her mother never knew about to keep her sex toys in the event her mother would visit. Her mother had a habit of just dropping in on her without calling first because she did not trust Jayne. But Jayne could access the storage are anytime she wanted to. Jayne did figure out a pattern to her mother’s visits and started to time them with her acts of self sexual pleasure with her toys. There even a few times Jayne had just got done putting her sex toys away right when her mom showed up. Jayne admitted to Emily this made her feel good, knowing she got something over on her mom. Jayne’s mother would have been OK with Jayne being a lesbian and having sex with women because of her aunt. But it took Jayne another 10 years before she made the decision to do so with the help of her aunt.
Jayne’s mother passed away 20 years ago which is when she started having sex with other women. She knew about lesbian sex from her aunt. While her aunt never would have had sex with her, she did try to get Jayne involved with women because she wanted Jayne to have a healthy sex life. Jayne could never bring herself to tell her aunt about her sex toys. Jayne told her about the women in the building that had lesbian sex. The week after Jayne’s mother was buried she approached Emily about having sex. Emily was her first and it has developed from there. Jayne has had sex with the same women I have, including Rose, Sister, my MIL, etc. She had sex with several other women as well. Even though Emily and other women had tried to encourage her to have sex with men Jayne would not do so because of what her mom taught her and her aunt being there in the same building. These women even had sex with Jayne after I or another man unloaded cum into their pussies and Jayne ate their cum filled pussies out. Jayne’s aunt passed away not too long ago. After the funeral she approached Emily and said she wants to consider having sex with a man and asked for advice. Emily talked with her about it and they decided I could be her first as Jayne knew about me from talking to Emily and other women that had sex with me. This is why Emily wanted to fuck me and partly why we fucked. Emily told Jayne she would help set it up.
I deflowered Jayne about a week and a half after the threesome with my wife and her mom. Leading up to being her first man that fucked Jayne, Emily wanted to make sure I would be able to last a while without cumming and at the same time have enough of a thick cum load to give Jayne a real pleasurable experience that she will never forget. She met with my wife to discuss it and plan it out. Here is how:
I did not know this at the time but Emily met and had sex with my wife to ask her questions about my stamina. My wife told her that if I go a few days without cumming my cum is really thick and heavy and when I cum it is with more force and she can really feel it when I cum in her, but I may not last as long as when I have sex either multiple times a day or multiple days in a row. She told Emily I can cum multiple times but as I do my cum gets really thin and watery. Emily told my wife she knows from the time we fucked. My wife also told her it makes a difference on how long the woman holds out before having her own orgasm. She told Emily since Jayne has had sex with women she should certainly know how to hold back until she can have a more powerful orgasm and that since she could do so it would make it more intense for me and I may potentially cum a thicker/heavier load into Jayne. Emily said she is correct but at the same time since Jayne has never been with a man that may either turn me on so much or turn Jayne on so much or both that neither of us would last very long and it would be over before you know it, kind of like it would if we were teenagers.
They both came up with the idea that I would fuck Jayne on Friday night. Starting on the Sunday before and going until early Wednesday evening I would fuck as many women or fuck the same woman as many times as I could possibly handle it. Then from Wednesday evening until Friday night I would not fuck anyone else until I had Jayne. The day they discussed this was on Friday, a week before I fucked Jayne. My wife came home and told me while Emily started to talk with Jayne about it.
I told my wife it sounds like a good idea but I had two questions. The first was do I have to wait until Sunday to start fucking women and the second was because we had been spending a lot of away from home I wanted to stay at the house at least until Monday, so which women can I fuck. My wife told me I can start right then and there and it can be any woman who wants to have sex with me.
I told her “you are first”. I was already naked with a semi hard on. She started taking her clothes off but I stopped her I told her I want a blow job from you with your clothes on. I was already sitting and she was standing. She got on her knees, took my cock, stroked it a few times then put her mouth on it. She stopped, looked at me, smiled, and said “mmmm tastes good, who was the lucky woman?” I told her a regular black woman I fuck at the adult book store. She then swallowed my cock whole. I reached down and pulled her shirt off, she had no bra on. I told her to tit fuck me so i could give her a pearl necklace that hung between her tits. She started combining sucking my cock with tit fucking my cock. It did not take long for me to cum. I grabbed my cock to guide where my cum landed on her. I told her to keep her mouth open, and shot one spurt into her mouth, then one on her chin, her neck and the final spurts of cum right between her luscious tits. After I was done I had her stand up and helped her out of her pants. Once she was naked I pulled into me and put my face right against her hot, shaved pussy. I could tell she had also been fucked and cummed in by a cock. I licked her hot slit, savoring the taste of cum in her pussy. I looked up at her and asked who the lucky guy was. She told me a young college stud who Emily has been fucking. She said they both fucked him and he unloaded in her twice. We were in the family room, I told her let’s go to the bedroom so I can clean her out.
We got to the bedroom, she lay on her back and spread her shaved pussy wide for me. I dove face first into her I meaty cum leaking pussy lips. I lapped up all of the cum running out of her, spread her open with my hand and stuck my face and tongue. When I brought her to orgasm it was so intense she pushed his cum out into my mouth. Her juices and his cum tasted great. I was getting hard again and wanted to fuck her deep. I started edging her. I did it so many times she started getting frustrated. I got on my knees, picked her up and lifted her above my cock, set her down ony lap with her legs wrapped around me and my cock plunging deep into her willing cunt. Once she bottomed out she started bucking her hips while I thrust up into her. She had a huge orgasm and squeezed my cock so hard I spurted in her very hard. When we were done and she lifted herself off of me a huge gush of cum drained out of her pussy and down her legs. She got one hersex toys to use as a plug to keep the cum in her. She then started getting dressed. She only put on a t-shirt and a pair of shorts, no bra or panties. When she put her shoes on I asked her where she was going. She told me she is going to Emily’s and her mom’s and I can have whomever I want to stay with me that night. She asked if she wanted to send someone over. I told no I can find a.woman to fuck and stay the night. She asked who.
I told her I will go back to the adult bookstore unusually go to, to see if I can find a regular there. If I can’t I told her I might try another or go “hooker hunting”. She knew what that meant. It means I drive around the neighborhood where the prostitutes normally are and bring one home to not just fuck, but I take her on an actual date. Depending on how she is dressed, what she wants to eat and how clean she looks and smells I also have had a.prostitute take a shower and have even bought their favorite soap and shampoo they take with them when we are done. I have helped turned some pretty rough looking hookers into sweet smelling, good looking women who anyone would want to fuck. Most of these women continue to take better care of themselves after they have a date with me. I pay them well for their time and then some when I fuck them. When I have spent the night with a prostitute it is usually in a hotel room that I pay for at least a week. We spend one night together while come and go after, fucking them when I want to. I knew of a couple of hookers I could try and contact to spend the night at my house.
I got dressed and we both left. My wife went to Emily’s for her sex party and I went back to the adult bookstore. When I got there I knew right away I was going to fuck a woman at least there. I know the manager on duty.and knew his wife was in the back rooms and was probably with a guy. I paid the entrance fee and as I was going back he pointed at the monitor and said she is not in a room right now. I went back and found her in the corridor. We looked at each other and I motioned for her to go into a room with me. She followed me into a room and as soon as she locked the door we were all over each other. She had on a very short mini skirt and a low cut t-shirt and no bra. Her name is Barb. Barb is 50 years old, about 4′ 10′, maybe 100 pounds with very small B size tits, very skinny hips and ass and a very narrow and tight pelvic area and pussy. Her shaved pussy has very thin inner lips that are well hidden by her outer pussy lips. If you did not know any better you would swear you are looking at the pussy of a minor teenage girl, not a mature woman. I pulled her shirt off while she pulled my shorts off and started stroking my cock. I yanked her skirt down, picked her up, carried her to the futon, laid her down on it, she spread her legs as wide as she could to take my cock.
I quickly line the head of my cock up with her tight opening and pushed in with one hard smooth thrust. She groaned very loud and tried to spread her legs wider to make it easier to accommodate my large cock. As I bottomed out inside her I pulled back and thrust in again, even harder. She cried out that time and hugged her arms around my back and hissed in my ear “do not stop”. I pulled out and shoved my cock in again and kept doing so, pounding her harder and harder each time. She started screaming in pleasure. I knew I was going to last much longer as her already tight pussy squeezed my cock hard. All of a sudden I felt her pussy convulse and I unloaded my cum deep inside of her. I pumped her small pussy so full it leaked out around my cock. She lay there and shook with the powerful orgasm she had. When we were done I pulled out of her and sat beside her on the futon. She told me it was wonderful and she wants more. I asked her what is she doing for the rest of the night. She said her husband is working the night shift, so either going home or staying at the bookstore. I told her she can spend the night with me at my house. She got up, got dressed and said let’s go, and said but im buying her dinner first as she went out to tell her husband. I got up, dressed and went out to the front. When I got to the front she followed me out to my car and her husband told us to have fun.
We left and I asked what she wanted for dinner. She told me and we went to her favorite local short order burger joint. We went through drive through got the food and then she wanted to go to an overlook to eat. We drive and ate on the way. By the time we got there she was naked, had her seat laid back all the way and was fingering her pussy. We got to the top and saw two other cars there. My car is a convertible and she asked me to put the top down. She wanted to put on a show. I recognized one of the vehicles, it belongs to a prostitute I know. Her vehicle is a camper van that she uses as a brothel. I did not see anyone in the other car so I figured the owner of the other car is her client and they were fucking in her camper van. Barb started giving me a blow job in my car. We then moved to the back seat where we tried to fuck but my car is so small it was not easy. As we were trying we heard the door to the camper van open and someone got out. Barb got worried but I told her to just keep sucking my cock. The prostitute, she calls herself Ginger Kitty, because she has red hair and does not shave her pussy. And the guy she was with walked over to my car. Ginger was pretty much naked. Even in the dark I could see cum running out of her red haired pussy and down her legs. Ginger said hi to me and called Barb’s name. Just as she did I started cumming in Barb’s throat. When I was done, she looked up and smiled at Ginger and said “mmmm, he’s got a tasty load.” Ginger told she knows and bent down and kissed Barb and they shared my load. The guy who was with Ginger was a young 20 something k**. He looked dumbfounded at the whole thing. They finished kissing and Ginger asked if she wanted to clean her out. Barb smiled and told her yes. Barb got out of the car, they both walked behind it, Ginger lay back on the trunk and spread her legs. Barb put her face in Ginger’s pussy and started eating her out and stuck her exposed pussy out for whom ever wanted to fuck her from behind. I told the guy who was with Ginger he had better stick his cock in her. He just looked amazed at the whole thing. I got out of my car, walked around it to behind Barb and shoved my cock in her pussy. I knew I was not going to cum right away. I looked over and saw his cock was really hard and he looked like he was going to burst. I told him to come closer, he did, I told him I’m going to pull out and you fuck her from behind. I pulled out and he shoved his nice cock into Barb’s pussy and started jack hammering her. Ginger started cumming in Barb’s face and the k** blasted his load in Barb.
Just then someone was coming up the road. The k** pulled out of Barb and pulled up his pants. Barb got off of Ginger and both casually walked to the camper van carrying their clothes with the k** and I following. The k** was freaking out thinking we were going to get in trouble. I told him to calm down and waved at whom ever was in the car that was pulling in. We got in the camper and I was feeling ready to cum again. Ginger and Barb got in a 69 position and I got behind Ginger and shoved my cock in her. I asked the k** if he likes sex with guys. He said he has never tried. I told him to get closer to me and took his cock my mouth. He is nice and thick. I have him a blow job and backed off when he got closer to cumming. I edged him a few more times. I could tell he was getting frustrated but told him not to worry. I told him to kneel behind me, he did. I reached back, grabbed his cock, lined it up with my anal.love tunnel and told him to shove it in me, hard. He did and it felt great. Right away he jack hammered my ass. I knew he would not last long and I was getting close to cumming in Ginger. I felt the k** unload deep in me and I started cumming in Ginger while she orgasmed around my cock and Barb’s mouth and tongue and Barb had a big orgasm too.
After everyone was done cumming the k** pulled out of me, I pulled out of Ginger and Ginger got off of Barb. The k** and Barb got dressed and waited outside while I talked and settled up with Ginger on what I owed her. I paid Ginger double what I usually would. She asked if I was going to take k** home with me and continue to break him in. I told her I am going to ask if he wants to come with me, but I want to fuck her some more and asked if she can take Barb home. She said she would and can join me at my house later. We went outside and I asked the k**, he told me his name is Justin, if he wanted to come home with me for more sex and told Barb Ginger is going to take care of her. Justin said he would love to come home with me for more hot gay fucking and sucking. Barb was cool with staying with Ginger.
Justin followed me to my house. I texted my wife and told her what has happened and what or rather whom I am doing next. She sent me pics of her hot sexcapades with a bunch of sexy, old, fat women. Some of whom I have never seen.
This is the end of chapter 1. Chapter 2 will be submitted after chapter 1 is published on this site.