Chubby MILF Seduction

 Chubby MILF Seduction

By KLynnCarlisle77

Tags: #chubby, #milf, #seduction, #oral, #anal, #sex, #spanking, #first #crossdressing

I already had a fetish and desire for a chubby woman, especially a divorced one.

A Fictional Story:

Intro In many months of being single I decided to find a good woman that will not cheat and is loyal.Through some friends at work who help me out in search of one. I already had a fetish and desire for a chubby woman, especially a divorced one. Chapter One It all started at work when at work when my friends wanted to hook me up with this woman that is 10 years older than I am. Her name is Jessica and she's 50. She's recently a few years outside of a divorce with two children that are older.

One of which is still in high school about to graduate. They spend half the year with their father to which this coming weekend starts their time for one month with him. My friends told me that this would be an opportune time to meet up with her. I was certainly up for it. I was longing to meet a good woman. By the way, she Jess was cheated on. Friday came very fast and clock was ticking towards the day. One of the guys volunteered to be the designated driver and had a SUV. Tom made the rounds after we got to our homes and took showers and changed clothes to make the rounds picking us all up. Jessica would meet us at Debra's place. Debra has a Pool house with a bar, basically her own nightclub. I rushed home to shower up, change clothes, and get a shave. 30 minutes went by and Tom arrived to pick me up then we went to 3 others to pick them up. An hour went by and we I was told by one Jess' friend (female) at work that knows Jessica's measurements are Height:5'12" Bust: 36DD Waist:31 Hips:47. I was very impressed. This gives me an idea of what clothing ie lingerie that I can get her as gifts. Night #1 of the Longest Weekend in Life: Damn time drags slowly in anticipation of meeting someone new and getting to an important social gathering. An hour and a half seemed like five hours. On the way there the time was killing me just waiting to meet Jessica. We finally get there and go in Debra's very nice house where she greeted us. She said Jess will be here any minute. Five minutes later Jess arrived in a Chevy Silverado HD 4x4, now that impressed me some more. Seeing her get out and seeing her for the first time was like seeing an Angel but only a much fuller version. As I approached her to meet and greet her I could smell her perfume, it was amazing. As the night went on and our conversation flourished into intimate touching of each other I could see it in her eyes, she, Jessica wanted much more. we didn't have to go very far to retire for the night. Dan & Debra gave us both the suite above the pool house to which looked way better than any 5 Star Hotel. It was almost 12 Midnight and Jessica went to her truck to grab her bags,while mine were already placed there by Debra. The "Special Package" of lingerie was also there as well waiting on me to give it to Jessica. I ran to help Jessica with her bags. She only had one and her purse as told me to carry her purse as we held hand going up to the Pool house suite. She had a mighty big purse. When we finally got to the room, she threw her bag on the chair and grabbed her purse off my shoulders. She put in on the side of the bed on the floor, then grabbed me to collapse together on the bed. We chatted away like we were teenagers for 30 minutes. I told her her surprise gift was on the table. I went and got it then gave it to her. Jessica opened it up and she smiled and said she loved the lingerie. She'd wear it tomorrow night when we stay again. She also liked the Bra-Panties & Stocking Match too. Since we'd be staying the whole weekend together here at Debra's place, Jessica said she wanted to be in charge and in control. Tonight would be Oral, Anal Fingerings, and some Spankings. She asked me if I'd ever been spanked by a woman and Mom did not cout. I said, "no". Jessica said, "tonight will be your very first but not mine doing the spanking". She said, "don't worry" as she heard me mutter, "oh boy". She said, "this is how I tell if yo're the right one". She got her purse and pulled out a small paddle leather-strap. She said, "don't worry, I'll take care of you honey-boo". She had me pull off all my clothes and lay across the bed. I did as she commanded me to do. Jessica asked, "are you ready for the test"? I relied, "Yes". Jessica asked asked again, again, I said, "yes". She smacked my ass and then said in an ordering fashion, "that's yes'mam". I exclaimed, "Yes'mam almost trembling. Jessica asked me if I respected women; I replied "Yes'mam", she smacked my booty 10 times. I could feel my ass already getting red. Jessica asked me if I would be her Little Bitch; I replied, "Yes'mam. She smacked my ass 20 times. Jessica asked me if I'd accept being dildoed; I had hesitation in my voice when I felt the leather-strap go across my painfully sore booty 15 times. Jessica asked Yes or No; I replied with pain in my voice, "Yes'mam". I was almost in tears. She asked me if I would be loyal to her; I replied with tears rolling down my face, "Yes'mam". Jessica smacked my poor painfully sore booty 20 more times.. At this point, I couldn't hold the pain back and started to mouth the pain in out loud crying. Jessica said, "it's not over yet, you still have 40 more licks to go." I said to Jessica that I wasn't expecting this at all". Jessica told me that if I wanted to be her Man, this is the Crucible Test that I must pass. She asked me, "do you want to be my Man?" I was about to reply when she laid it on 15 more times. Then I cried out in tears, "Yes'mam". Jessica hinted that I was doing good at this point. Jessica said, "two more questions." I can really feel my poor little booty stinging like it was on fire. My breathing was fast trying to make the pain go away to which wasn't working at all. Jessica asked me; "if Itold me to wear anything would you?" Before I could answer, I got 15 more lashings. She repeated the question; I replied, "Yes'mam". Jessica said, "Last question; will you pledge your eternal love to me"? She the strck my ass 10 more times. I was crying like a little boy with slobber coming out my mouth and snot coming out my nose. I cried out once again; "Yes'mam. Jessica gave the final 10 spanks with her hand, then rubbed my booty. Jessica said hold still while she gets the Aloe Vera Cooling Gel. She applied and rubbed it in on my ass. She told me to lay still the laid down beside me, the rolled me on my side. She caressed my head in her lap and looked dead in my eyes and told me, "you passed the test Honey, you're mine now". She the kissed me, even french kissed sucking my tongue like a dick. She caressed my face and told me that she loved me and would take care of me the whole weekend. Jessica reached down and started giving me a hand-job jacking me off until I shot cum out then sucked it off my dick and stomach, then she kissed me again. Jessica released my own cum into my mouth and made me swallow it. She said,"get used to that". I replied; "Yes'mam in fear that I would receive more of what I just survived. Jessica said, "that's a good little boy". She helped me up off the bed then put some more Gel on my little booty, this gel was a super gel that worked fast to cool the pain down. She escorted me to the bathroom so I could see how red my booty really was. She gave me a hug from behind and whispered in my ear reassurance everything was going to be alright. I began to cry like a little boy, when turned me around and hugged me some more, then picked me up on her hips like a kid wiping away my tears like a mother would. I clanged to her like she was my mother. She softly caressed my booty with her soft hands. I felt her slip her middle finger in my booty-hole finding her way to my prostate that she began to rub that made me feel so damn good that I shot cum all on her as she held me. I never had a woman do all of this to me. The seduction was so euphoric it was mind-blowing. She took me back to the bed and laid me down then went down on me sucking my dick once again. Again she came back up and deposited my own cum in my mouth to which I swallowed, she did not have to make me this time. I was really her's, I was her little bitch...and I loved it, I accepted that fact about myself. She told me that we'd be going to sleep now so we can get up early to enjoy breakfast

Debra would be making for us. Jessica removed her clothes and came back to bed, both of us slept naked together, she spooned me the whole night so I could have something soft for my little booty to rest against.

[END OF CHAPTER 1]

You know you want more of this. Don't lie.

Chapter 2

The Next Morning:

I did not hear the alarm clock or did we have one. I could barely hear Jessica moving around in the bathroom a bit. She came back to the bedroom and got back in bed. She took her hand and softly caressed my booty and rubbed my leg. She kissed my neck as she rolled me over. As I rolled over my eyes began to open.. When I saw her lovely eyes and face, Jessica said, good morning Baby.. Are you feeling okay from last night? I replied, Yes'mam and good morning Honey. Jessica told me that if she was too rough that she was sorry but it had to be done. I told her that it was something that I really needed. Jessica replied, oh Honey, I really hope that you don't get up and leave. I replied, I'm not. I really felt loved when you took care of me after. I can see that Jessica was starting to cry. I asked her, what's wrong? She told me that many men cheated on her and she was sick of it. The "Test" was to see if I was worthy enough. I caressed her hair and head while telling her that was cheated on. Jessica grabbed me and held me tight while still crying. Her body felt amazing next to mine. My dick was rock hard and she noticed. She rolled me on my back and got on top of me. Jessica rubbed her pussy on my dick...Sigh deeply... Her pussy felt fucking so fucking great. She collapsed on top of me and just laid on me for 15 minutes. She and I cummed all over each other so much that we needed a shower. She muttered breathing hard in my ear, wanna take a shower together? I told her, Yes'mam. Jessica told me that in private I could just say yes or yes Jessica. Out in public, it better be Yes'mam. If you don't gonna get a spanking and that's when she rolled me on my side and popped my booty. I replied, Yes'mam. I started to ask her if we could be boyfriend &...she caught me and she once again started crying, I hugged her and gave her a few minutes. After she stopped, she finished what I was asking her and said, YES! I even started crying and she hugged me too. Jessica said, enough of this crying, lets get a shower together. She said she brought her stuff. I forgot my stuff. She giggled, You know what that means? You're gonna smell like me all day. She took my hand as we walked into the bathroom naked together. She started the shower... Jessica took her shampoo-conditioner and washed my hair for me. It felt good. Then she took her loofah and her body wash and scrubbed me down really good. She then took some in her hand and went up my ass-crack went back and forth to which made me get hard the she rubbed my dick down. Jessica told me to hold my hand out and told me to lather her hair really good. I did. Jessica gave me her loofah and put some body wash and had me scrub her down and I did. I also grabbed the body wash and did as she did to her ass crack and pussy with my hand. I had her moaning. We stood together under the shower and just held each other by the booty and kissed each other. That lasted 10 minutes. Jessica shut off the shower and we both stepped out to dry each other. Jessica asked me to comb and brush her hair, as I did. Her hair is silky soft. Jessica asked me if my booty still hurt. I said it does a little. She said she had a extra pair of silk panties that would be softer on me. I went to the the bag I brought and got out cargo shorts and a polo. Jessica got that pair of black silk panties for me. She put them on me and surprisingly they fit and that I was her size. She cupped both of my ass cheeks and kissed me. Then she gave me a soft pop-slap. We got dressed to go back to the main house for breakfast with Debra. Jessica reminded me to bring my cellphone charger to put it in her purse. We got to the kitchen Debra greeted us good morning, both of us replied the same and hugged Debra. Debra noticed that we both smelled the same. I told her I forgot my shower stuff and had to use Jessica's. Debra asked if we wanted to go into town to get things for Jessica said, Yes'mam and thinking about what Jessica sad, I said the same. I kept think about Jessica's response. When we got finished eating, I pulled Jessica to the side and asked her why she said Yes'mam. She said that Debra introduced her to BDSM and she used to be her Dom-Mistresses training her. Jessica asked me if I would be comfortable with telling Debra about last night. I told her, Yes'mam. We went back to talk with Debra before we left. Jessica started telling Debra what transpired last night. Debra's face perked up. Jessica asked me to pull down my shorts and panties to show my little red booty. I said, Yes'mam, and and did as asked. Debra ask Jessica if she could rub my booty, Jessica agreed with a Yes'mam. Debra came over to rub my booty. Debra asked me if I was okay. I told her, Yes'mam. She asked me if I ever was spanked by another woman prior. I said, No'mam. Debra asked if I cried, I said, Yes'mam. She said, awe, that's usually the case for first-time newbies. She even asked how is it wearing panties, I said, these are actually comfortable and soft. Debra gave Jessica her other credit card to get some more across the street at the Mall. I was like thank Mam. Both her and Jessica came over and took one ass cheek and rubbed me and told me welcome to the BDSM Club. Debra said load up in her SUV. Jessica took the front seat while I sat in the back. Along the way to town Jessica asked me if I wanted to get rid of all that body-hair. I told her, Yes'mam I would like that. Debra said she and Jessica would help out in that department when we get back. Debra told Jessica, ya might want to get him a enough bras, pantyhose to go along with those panties and oh, a few dresses too. There's a wig store in the Mall, go by there and get him an appropriate one that's long enough. Too, heels too. We can both use our make-up on him. Jessica told me that she would be moving into Debra's pool-house so I could get out of my rental-lease and join her. I got to thinking that saving that money would go along way and that I really liked the pool-house. Plus, having that much privacy would be great. I asked Debra if Tom her husband would help me move, she said he will and both her and Jessica would too, don't worry about it. I asked Jessica how many times would I have to cross-dress. She told me as much as I wanted but a few times a week for us Girl's pleasure. (I really didn't mind having a little fun with the girls.)

We arrived in town at the Grocery Store where Jessica and I split off to the Mall next door across the street to shop for clothes, make-up, heels, and a wig; and some other things. Jessica took my hand as we walked to the Mall. She handed me her purse to put over my shoulder.

[TO BE CONTINUED]