This story is not quite a MILF, more like a young woman and older guy.
I interrupt the regularly scheduled program to tell you about Dani. She was a 25 year old I met back at that church. She had recently graduated from college with a master in biology. She was not working in her field.
She had a troubled past. No one really knew what happened and she did not talk about it to anyone. I tried to break past her barriers. I got a little at a time. Simply her life had been hell ever since she started to menstruate.
I won't give the specifics of what happened to her, but I felt lucky to become a person she could trust after a lifetime of heartbreak!
I tried little things. Gave her notes. Put her Jacket on her. Paid for part of her lunch when a bunch of us went to lunch after the last service. Asked to go on walks and just talk. As time went by, she started to give me hints of things. She also started to relax around me. What started very slowly, doing something once every three months, progressed slowly to once every two weeks.
Then, it happened! One day, I called her on Wednesday and asked if I could come over Saturday morning and we would spend a part of the day together. No plan, it would be decided when we were together.
When I knocked on her door she answered it. She invited me in and started an awkward conversation.
"You know I like you, but I have sworn I will never get married."
I didn't know what to say. She went on.
"I don't trust men. They have always hurt me. But, you. If this is to continue, I must be in charge."
I just looked at her. I eyed her up from top to bottom and back. She was waiting for me to say something.
"Did you think that would make me run away from you?"
She nodded, I continued, "It didn't. If you have been hurt so bad, I will accept your terms until you trust me."
She stared at me. I was not sure what to think. I could not tell if it was a glare, or what! Time passed. I think it was almost 10 minutes of us just standing there staring at each other.
"Okay," she said, "but you'll have to do everything I tell you do without any hesitation."
"Only as long as you don't ask for anything too great and too fast." She nodded in agreement.
"My first command is for you to take off all your clothes."
I looked at her, I started to unbutton my shirt, while saying, "Is it okay of I leave my socks on? i get cold feet very quickly." She nodded in agreement.
I was quickly standing before her naked, except for my socks. She walked over and looked at my manhood as limp as it was. Told me to stroke it until it was hard. I did. She looked at for several seconds. Turned and walked away.
I just stood there. When she was across the room, she turned back to me and asked, "Would you like to fuck me?"
I looked her in the eyes, chose my words very carefully. "No, I would not like to fuck you, I would like to at a time of your choosing to make love to you."
She smiled, "Good answer." Paused and continued, "I have thought that, but since you made the distinction I will continue. Do you like pain?"
I replied, "Not really."
She then proceeded with a list of different BDSM things. Some I said yes to, others, no, and many I had never tried and would be interested in it.
She then took me to her computer and showed me a website that was dedicated to BDSM fetishes. She said that she considered herself Domatrix or Mistress. Look at me and asked, "You want to be my slave?"
I looked her up and down, again, and finally said, "Okay," not knowing what it meant.
She told me to sit down pour a cup of tea. I sat. She left and came back a few minutes later. She had changed in to a Mistress outfit, with nothing covering her nipples or pussy. But she was wearing a Strap-on.
My EYES were LARGE! I looked at her in awe. She was prettier than I had ever seen her before. Her body was more lovely than I could have imagined before she her dressed like this. I think I stood there and stared!
She gently turn my head to look her in the face. "You will never get this, unless you please me. You will not have any sex with me until I am ready for you to do that with me. Then, you will only do what I tell you to do and nothing more. I will test you. Each failure and it will be longer before you get to put that (indicating my cock) in here (motioning to her pussy). Are you in agreement to do what ever it takes?"
Without hesitation I enthusiastically said, "YES!"
She smiles. I think I passed her first hurdle. We say and had tea and talked about that website. her kinks, what kinks I may have or were interested in.
It was in many ways the first real conversation we had ever had. She could be "real" as she explained things to me. She told me no details, but every time she had ever had sex before in her life was "illegally." She was victim of incest and rape. No wonder she did not trust guys.
My heart felt for her. If this helped her heal, I was going to do all I could to help her heal.
In future times together she would put cuffs on my and tease me. She tied to to the four corners of the bed and played with my cock until I came. All sorts of stuff. Our once every week quickly became a twice a week thing.
One night each week after work we would go to dinner and talk about what she was going to do me on Saturday. Once we went shopping at an adult store.
She told me that she had never had sex with a woman, but the group at that other website taught her things to do and she went to events and they showed her what to do. She trusted women, but not men.
One day we were talking about anal sex. So, when we went shopping we bought two sets of butt plugs. We started with the smallest. I used some oil and played with inserting it into her ass, she did the same to me. Finally our asses were conditioned to the point we had the plug in all week. We moved to the bigger size. Finally the biggest.
She also had we "learn servitude." I would make tea and serve her. One Saturday, I came over and she had the tea ready. Had me strip down to just my socks and shoes. Had me put on an apron. Shortly after there was a knock at the door, she ordered me to answer it. There was a lady about my age. I let her in. I was introduced to her and bowed. Before it was over there where six women present and I was serving tea and cakes to all of them. Dani and five friends. All sorts of ages were present.
They did all the think guys do to serving girls to me. Gave me an understanding if what waitresses go thru. But, I did it all for Dani and her trust.
Once it was over, she walked over to me as I closed the door behind the last one to leave and whispered to me, "Thank you." A quick kiss and she back to her "cold self."
Once we had built up our asses for sex, she told me one day that my ass was hers. She put on her strap-on. Fortunately is was the same size as the butt plug I was wearing. She bent me over a chair. I offered her my ass. Slid that strap-on into to me, she pumped until I almost collapsed. I had never had an orgasms like that before!
Once I recovered, she simply said, "A deal is a deal." While bending over the chair. I took her by her hand and made her stand up. I said, "This is the first time I am going to disobey you. Thank you for the offer, but I don't think the time is right for me to do that to you."
She looked shocked! Puzzled! Did not know what to say or do. I gave her a small peck on the lips, and a gentle one on her forehead.
I think I saw tears swell up in her eyes, it did not last long. Just as quickly her hard self was back.
Each we she told me what we were going to do on Saturday. And we did. Finally, a week came when she let me touch her body. I gave her and complete head to toe, front and back massage. She really enjoyed it. Especially me fondling her breasts. She did not admit it, but I think I gave her a small orgasm.
One Saturday we met later than usual. She took me to a place that had a dungeon in the basement. She said we were going to put on a show for people, and then have a question and answer time afterward.
Okay, I was up for it! I enjoyed my time with Dani. I could tell she still had her defenses, but they were weakening. She trusted me, more than any man, but she still wanted me at a distance.
At this show, she put me in a stock. I was bent over, nude. Once the curtain opened people were quiet. She walked out and said, "Welcome here we will show show you how to peg a guy safely." She went on to explain how she had prepared my ass with butt-plugs. Finally it was time.
"You ready?" She asked me. I nodded.
She got behind me and pressed her strap-on between my cheeks, slowly separating them, my asshole felt it push into it, and part with a little resistance. Finally she was into me as far as it would go, she continued to pump into and out of me until my knees gave out! She steadied me. I had had another of them male orgasms. I was semi-conscious for a few minutes. I heard the crowd applaud.
She took me out of the stock, again kissed me and said, "Thank you."
"You are very welcome, it was my pleasure." She stood there and talked to the people that had questions. A few people asked me some too. I answered as best I could.
When we got back to her place, she let me not only walk her to the door, but hold my hand the entire walk. She even let me kiss her goodnight. I felt like a million bucks!
The next time we were together the hardness was back! We ate and talked about Saturday and whatever. On Saturday I arrived and got undressed as usual. She was already nude, wearing only a housecoat when she answered the door.
That was different. She let me touch her all over her body. Even her pussy. I kissed her all over. From her jaw, to her toes. I back of the knees. I hit all of her erogenous zones. except in and around her pussy.
Next week she let me go further. Just could not insert a finger inside of her. the week after I got to lick and kiss her pussy! One little step at a time and she was learning to trust me.
Then, came the week she let me insert a finger into her pussy. I did the best I could and hit her G-spot! I had her moaning and flipping and flopping all over the place. She ever left this world for a period of time. When she finally became aware, she looked at me with a puzzled look. I had cuddled up to her and just held her tight. She smiled. I said, "You're welcome."
She blushed a little. "What did you do to me?" I explained that I had given her a massive orgasm and she effectively passed out from the sensory overlord. So, rather than do anything else, I took her in my arms and held her until it passed.
She looked at me. I was unsure of what the look meant. I think she noticed my confusion, and smiled.
Jokingly she said, "I like that. Whatever you did to me."
"I am glad. You know I do care about you?"
She just smiled a big smile.
The next week, she had me show her how to give a blow job. She did not like the cum in her mouth! She was bad at it. I also noticed very quickly that she did not want to do it and was not going to learn how to do it better. We spent most of that day with me in "extended foreplay." She finally let me bring her to several major orgasms. She allowed me to use my tongue. When I got to the small i, she bucked so hard, slammed her legs shut on my head, and then "shutdown."
I cuddled with her again. This time her recovery was a little quicker. When she came to, she was still harsh, but did say, "Thank you."
"Just part of the service, ma'am."
For the next several weeks we were in a rut. I would come over, strip down. She would lie on a blanket on the floor and expect me to service her. I did. It was the longest case of "extended foreplay"I have ever engaged in.
Then, came a "break-thru." I came over and got undressed. She was already nude but standing in the living room. Once, I set down my clothes, I looked at her. She just stared at me, from top to bottom and back up. Finally, she shrugged her shoulders and said, "Is there a way for you to fuck me without touching me?"
I thought about it. I asked if when fucking her and my balls it her if that was touching her? I also asked several other questions about what her definition of touching her was. It boiled down to, I had to do it without ever having my hands touch her anywhere. I thought about it.
Finally, I said, yes there was a way, she would have to be in an awkward position. She inquired what that would be. I said either bent over the back of the couch, or over the dining room table. She chose the couch.
She bent over it. I told her she had to move herself up and over a bit more so her pussy would be at the right level for me to enter her. She did. I grabbed my cock and stroked it until it was hard. I stepped into her, lined up her pussy with my cock, put the head slightly inside, grabbed the couch and pushed myself inside of her! It was tight and wonderful! Everything I hoped it would be! I stood the for several seconds just enjoying the feeling of my cock inside or her wonderfully tight pussy! I started sliding into and out of her. gently at first, I increased the speed. Did never get to hard in my thrusts, just as I was about to cum, I pulled out and blew my load on the back of the couch.
I went and got something to clean it up. She watched me. When it was clean to her satisfaction, she said, "Good job."
I wonder what next, waiting for her to give me a clue. "You did fuck me with touching me. It was nice. It seemed you were almost out of me each time then seemed to thrust down and I made your packer go straight into me."
I smiled. She glared at me. I said, "I did that so my head would hit you G-spot upon entering again and go to your A-spot to give you maximum enjoyment."
She tilted her head, thought about it and nodded.
"What is you favorite way to fuck a woman?"
"Depends on my mood. The first time I prefer missionary, so I can see the fire in her eyes. I also like cowgirl and reverse so she can control what is going on and make sure her clit, G- and A- spots are hit."
I could tell she was thinking about what I said. She went and got us some iced tea. When she came back she asked, "What is cowgirl and whatever?"
I explained as best I could what they were. She seemed to like how I described them. Her next command was, "Lie down and get yourself hard."
I did! She stood over me and squatted down, with a little difficulty, and an insistence that I not help her, she was on me with my cock inside of her. "You come inside of me, I'll kill you." She started going up and down. Up and down, on and on, until I knew I was about to come. If I tried to touch she slapped my hands away. So I was unsure what to do, I said "I'm about to cum."
She leapt off me! Just as I exploded into the air! She leered at me. "You won't let me touch you, so all I could think of was tell you." She nodded in acknowledgment.
She then knelt over my face and said, "Do whatever."
I started eating, licking, I never used my hands. It was difficult but I think I pleased her. After awhile she asked if I could get hard again. I said I could. She commanded em to make it hard.
She then mounted me with her back to me. I just laid there and let her go up and down until I was about to cum again. This time I chose to be a little more prepared and aid it very casually it. "I am about to cum again."
She got off, and I didn't cum. She stared at it and the at me. I explained that if I was not kept stimulated all the way to the end as last time, I won't cum.
She looked at me, tilted her head, nodded and smiled.
Then, she had me playing with her body with everything at my disposal, hands, fingers, lips, tongue, and had her cum several times before a massive one shut her down again! I assumed the cuddle position until she came around.
She mouthed a thank you. Then, she actually wrapped her arms around me and hugged me. I had never gotten more than a handshake! Maybe a peck if I initiated it.
After several minutes of lying arm in arm, she reached down and grabbed my manhood. Started stroking it, within several strokes it was hard again.
She rolled onto her back, saying, "Show me what is so wonderful about your favorite position."
I got above her in a push-up position. She spread her legs wide, I lined myself up, and lower my chest onto hers. I pushed my cock into her slowly. When I was in all the way, she curled her legs up behind me and pushed me in further. I looked her in the eye, saw a fire get brighter, and kissed her. She did not resist it. Her legs relaxed and it took myself back out and then in again. Obviously repeated this until I was about to cum. As I put my arms down by her side to lift myself off her, she wrapped her arms around my neck, forcing my head to kiss her, while her legs pushed me deep inside of her.
I panicked! I didn't know what to do, and it was too late! I came inside of her. As soon as I finished milking myself out of habit, I got up and started say all sort s of stuff. All about her not letting me get off her, and cuming in her, and etc.
She just laid there. I asked, "Now what is going to happen?"
She calmly, "Nothing. I know you love me. I do not love you. I am never going to get married. I used you to show myself something wonderful. Now, I know how to get a guy on my terms and use him when I have the sexual urge. I want you to get dressed and I am never going to see you again. Never call me again, and don't ever come here again. Goodbye."
With that she get up and walked to the bathroom. I did not know what to do. I stood there. With the door between us shut, I slowly got dressed. I could hear her crying. I could not tell if it was tears of joy, regret or what.
I walked to the door thought about knocking, decide against it. I had been honorable up to that point and had done what she asked me to do. I didn't feel right about saying anything. So, I left.
She was not a church the next day. I didn't call her. I honor her request. A couple weeks later I drove by and did not see her car, so I chanced stopping and asking the apartment manager about her. He said that she packed up and left, did not leave a forwarding address. He said she said she would stop by sometime and get the deposit check.
I never saw her again. If it helped her to heal by hurting someone, I can live with that. Maybe I helped her get back what several "men" had taken from her. I know that being a victim of incest and rape took it's toll on her. I hope she is well!
6 comments
It was a good story
Thanks!