The following is a true-to-life sexual experience involving friends helping friends. Mrs. Pennington was the MILF next door, and I totally had the hots for this woman. In addition to rocking a perfect MILF body, she had fallen into difficult times financial while going through a bitter divorce. Her husband had left her, choosing to chase after younger women.
Friends Helping Friends With Benefits
It wasn’t even one college girl in particular. He didn’t want to admit that he was getting middle-aged. I guess his balding ass found it easy to impress these impressionable young things with his cash and Ferrari. While I admired his choice of sports cars, I always said to myself, “What a complete dumb-ass to leave a piece of hot MILF pussy like that!”
Mrs. Pennington had moved into the humble abode next to our place. She was left with raising her two middle-school-age children alone while her soon-to-be ex was off showboating his flashy cars and college-age women.
My early twenties wife and I had our “little mistake” while still in high school, so we knew about unwanted (at the time anyway) lifestyle changes for sure. My young wife and I got to know Mrs. Pennington really well and frequently babysat for her so that she could run errands and attend a yoga class.
Sometimes she would call my wife to go out for coffee or drinks together. Mrs. Pennington just needed somebody to talk to and share her pain of being single again without a job soon. Often my wife would come back nearly in tears herself as Mrs. Pennington’s husband had hired a hotshot lawyer determined to fuck her over during the proceedings.
“Mrs. Pennington is so wonderful. What did she ever do to deserve this?” my wife would say. I would listen and nod as my wife told me (almost on a daily basis) about the pain and loneliness that Mrs. Pennington was experiencing. Often she would say, “I wish there was something we could do for her.”
I have to say that the thought had crossed my mind about “helping Mrs. Pennington,” but I didn’t dare tell my wife how much I would “really like to help her between the sheets!” Finally, after one particularly bad night of drinking way too many dirty martinis with Mrs. Pennington, my wife slurred, “Isn’t there anything we could do for her?”
I said, “Well, what would you do for her if you could do something?” “If I were a man, I could take her in my arms. Hug her tight and let her know that she is special, that she is beautiful, that she is hotter than any piece of ass her ex-husband is trying to fuck.”
My wife and I had only been with each other sexually. So, I don’t know what caused me to say what follows; “What about me?” I asked. “Wouldn’t you get jealous if I had an affair with Mrs. Pennington?”
“No, dumb ass,” my wife said, “You and I would both know that it was platonic and only short-term so that she isn’t all alone during her divorce. Women have needs, especially MILFS! It’s not like she can go out and hook up with guys looking for some hot MILF Pussy as that’s exactly what her husband wants to discredit her.
This would be more like helping her out temporarily, one night, maybe or two every once in a while when I am on my period. Just think of it as if you were helping Mrs. Pennington out with anything else. “Holy Shit,” I thought this was much better than cleaning the garage or helping her with yard work!
“You could, you know, help her! Why don’t I talk with Mrs. Pennington and make all the arrangements?” After all, I start my period tomorrow. “I’ll set up a day and time, and then you can go over to her house and, you know, take care of her MILF Pussy, and I can watch all the kids for a couple of hours.”
The next day, my wife came to me all excited. “OK, I’ve set everything up for this Saturday. I will babysit her kids here, and you can go over to Mrs. Pennington’s house at 7:00 pm. She will leave the door unlocked and wait for you in her bedroom. Take your tool belt just in case any private detectives are still out front.”
Fuck Thy Neighbor, If You Can!
It was only Thursday, and my wife was on her period. I wanted to jerk off to my favorite porn stars but knew I better save everything for this “free hall pass fuck” my wife had just given me. Finally, Saturday came around, and it seemed like a month before the clock struck at 7:00 pm. I put on a work shirt and my tool belt to make everything look legitimate and headed next door to Mrs. Pennington’s house.
The door was unlocked, just as we had planned. I had been in her house many times over the years but never up to the second floor. Slowly, I walked up the stairs and saw that one of the rooms had the door cracked open slightly. I went to that door and slowly opened it.
“Mrs. Pennington?” I whispered. “Yes, Brian, I’m in here,” she replied. I entered the room and shut the door quietly behind me. The room had all of the shades and curtains closed with a beautifully lit Aromatique candle on her dresser. I could see that Mrs. Pennington was in bed. While this was a bit too planned for me, I slowly undressed and walked over to the bed.
She seemed a bit nervous, which was OK since I was too. I mean, my MILF Pussy was going to come true, but this was almost too fucking easy! As I lay down, I tried to remember everything my wife told me about their intimate conversations.
“Mrs. Pennington, you are so beautiful and kind and generous,” I told her. “You are such a wonderful woman, and I am honored and delighted to be with you tonight. You will be only the second woman in my life,” I stammered. Mrs. Pennington was very slender, with brownish/blondish hair and totally amazing natural breasts.
She loved to laugh and was among the nicest people I have ever known. I held her in my arms for a long time and stroked her long hair. Sometimes I would stop and hold her hand. Finally, I leaned over her and kissed her. It didn’t take long for our tongues to find each other as we embraced in a French Kiss like it was our first time.
Kissing Mrs. Pennington deeply awoke the sleeping inner MILF that had been hidden throughout the divorce proceedings. She responded by wrapping her arms around me and pulling me tightly against her. She smelled so sweet and felt soft.
I moved my hand from her head to her natural tits feeling her nipples harden. They were small and firm and begging to be sucked. I moved my mouth from hers and gave each nipple just enough attention while she moved her head back and forth in agreement.
Mrs. Pennington then responded by spreading her legs a little allowing me total access to whatever move came next. I reached down carefully, knowing her MILF Pussy was on fire. Suddenly, my nervousness about being with someone other than my wife was set aside. I was now the leading man in a super hot MILF Porn movie scene.
My now confident cock was now hard as a rock. Mrs. Pennington leaned back and opened her legs farther. I slipped my fingers into her warm and now completely saturated MILF Pussy. She moaned like she had been holding it in for ages. Mrs. Pennington begged me to “get inside” her, and I was eager to accommodate her request. I slowly began to put my cock inside her when she grabbed my hips forcibly and pulled me deep inside, wrapping her silky legs around me.
With my hard cock now pumping Mrs. Pennington, it did not take long before she let out a primal moan in preparation for a much-needed body-shaking orgasm. Her body tensed up, and then I could feel her pent-up sexual excitement pulsating throughout her whole body. Her MILF Pussy contracted countless times, gripping my cock before finally tapering off.
I was taken aback by Mrs. Pennington’s emotional facial expression, which was emotional given her circumstances. I didn’t want to ruin this special moment by continuing to fuck this beautiful woman silly as she basked in her climax. I knew my time, and hopefully, times would come. Finally, I rolled off of her, looking up at the ceiling fan, barely cooling the sweat we had both worked up.
I held Mrs. Pennington another ten minutes or so before kissing her gently on the cheek, thanking her for allowing me to share such a special bond with her. I got up, gathered my clothes, and left her bedroom. I strapped on my tool belt and then slipped out of the house, desperately needing to cum myself.
MILF Neighbor Fucking Finale
“So, how’d it go with Mrs. Pennington tonight?” my wife asked. “Nobody ever needed to get laid more than Mrs. Pennington did tonight. Now, come over here and taste her MILF Pussy on my cock while you finish me off with a blowjob and not a blowjob tease either.
I’ll explain later, but I really need to cum now, babe! Mrs. Pennington needs some regular sexual attention, and I didn’t want to press her into more than she could handle this evening.” With that, my wife got down on her knees and licked all that remained from the only other pussy I had ever fucked besides hers.
Mmmm, Mrs. Pennington sure tastes good,” she muttered while gobbling down on my cock. I only needed a few well-placed exert strokes from my wife before I started pumping cum down her throat. Luckily, my wife is an expert cock sucker and never misses a drop.
However, this time, she allowed a little cum to run out of her mouth, telling me she wished Mrs. Pennington was there for friends helping friends’ neighborhood swingers snowball!
