My Best Friend's Mom Needs a Boy-toy
Chapter 1

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Consensual, BiSexual, Heterosexual, Fiction, Humiliation, Rough, Spanking, White Female, Hispanic Male, Anal Sex, Cream Pie, Exhibitionism, Masturbation, Oral Sex, Petting, Voyeurism,

Desc: Erotica Sex Story: Chapter 1 - My girlfriend got all gender confused and left me high and dry. Now, I have a shot at my best friend's mom. I hope she doesn't know I have a crush on her.

My best friend Tommy was a sort of guy that never spreads a rumor and usually keeps his mouth shut if he doesn’t have the answer to a question that all of us consider essential to smooth sailing on the sea of love. Tommy was a stand-up guy; he would be there to do the right thing because loyalty to him was the most important ingredient in any relationship. I had seen him get fucked-over by more than one girl taking advantage of his romantic inclinations and I had to bit my tongue to stay out of his doomed-to-fail love affairs that tended to be disgracefully one-sided and not in his favor at all. His last fling was with fucking Marsha Simpson. She was a bitch of a female troublemaker always ready to stab someone in the back providing she got something out of the deal that made things easier for her and not concerned at all with the impact on guys like Tommy that worshipped at her nasty feet. I knew he was far too trusting to put two and two together and question why she was still out in the wastelands of the sticks and not a player in the game of thrones back in capitol city.

I had to admit Marsha was a real hot number with her pert unfettered boobs and her sweet ass that looked like a heart-shaped invitation to unconventional warfare behind enemy lines. I knew for a fact that Tommy was not the kind of guy to be dipping into that honeypot without some crash course in anal amusements. He would too afraid of messing up and getting laughed at for making some mistake like a silly schoolboy with no idea of how to go about defeating a nubile female’s sphincter. In a way, it was probably the best thing that could have happened to him because eventually Marsha would betray him with some young lad with an impressive cock and brag about how the new guy really know how to slap the salami to her with a vengeance. It would just serve to make him feel less self-confident and that was not in his best interest at all.

I had no right to talk because my love life was a total disaster the past year. My supposed steady Heather was suddenly all hot and bothered about getting “closer” to her fellow cheerleaders and I suspected she had fallen prey to the ego-building spider’s web of beautiful girl loves beautiful girl blues. I found that it made me jealous to watch Heather and her new heartthrob Carmela playing “spin the bottle” in the back seat of my father’s old car. They considered me an “insider” to their sexy game of girl on girl relationships. I wondered how my Heather could get along without my eight inches to keep things on an even keel when things got down and dirty. I guess those two beautiful girls could find other distractions to keep them busy when they got hot and heavy under the quilted spread we used because the car didn’t have a heater. Every now and then, Heather would throw me a “bone” and let me take her from behind providing I only used her rear door and not take any chances with having a family before the right time. I have to confess I loved those moments when she just pushed her ass back at me and tell me,

“OK, Harry, do me quick. Make me take it and don’t stop until you get a good tingle.”

She sounded so much like a martyr that I fully expected her to say the rosary when I was pounding her with maximum enthusiasm. I knew she loved it from the way she was grunting each time I bottomed out and she clung to my arm so tightly that I thought she would cut off my circulation.

One time, Carmela caught us humping like that she was not at all amused.

I guess in her mind, she was the one that really loved Heather and that I was just another hard dick with no conscience when it came to free pussy. In a way, she was right on the money, but I did have sincere feelings for Heather. Of course, they were based more from comfortable familiarity than from any unbridled passion for her personality or some pretense that she was my one and only “soul-mate” forever and a day.

I knew when Heather wanted it hard and dirty from behind and I knew when she needed it nice and gentle with lots of kissing and tongue action buried to the hilt in the wet and wonderful wide-open world of Heather pussy-land.

She was sort of conflicted in that regard and I suspected it was an indication of her confusion over the simple choice of desires for a male or a female to fill the role of a full-time permanent lover. Looking at it from my genitalia focused point of view, I failed to appreciate her fickle nature about her urges to spread her knees in any direction other than my own and shamefully considered any dalliance with the same sex as a one-time experimentation to expand her sexual IQ. I was as surprised as everyone else when she finally declared her loyalty to the other side and left me out in the cold with a hard-on and nowhere to go.

In a way, I guess I was being unfair to Heather because she was terribly gorgeous and I hated to lose to a woman. If she had bent over for a hulking he-man with a two or three inch advantage over me, I could accept defeat gracefully. It didn’t seem fair that my competition was another equally beautiful female with huge boobs and an ass that could wear any flag decorated pair of bottoms with the respect it so richly deserved.

That was the sad story of my current status of frustration driven to the sin of self-gratification with dated issues of “Playboy” spread out before me like a line-up in a house of ill repute. Unfortunately, that scene was played out whilst on a sleep-over at my best friend Tommy’s house after a long night of beer and illicit video tapes. Tommy had already left for his part-time job at Luigi’s pizza palace where he was famous for his pizza tossing skills that thrilled the girls rubbing their little twats on the hard surface wooden benches. I suspected they were more interested in watching his bulging muscles on heavily tattooed arms than in the delicious orbs spinning just below the raised ceiling in front of the ovens.

I was gratified that Tommy had left me on my own because it gave me an opportunity to put his dirty magazines and my frustrated cock together for a real fun time. I thought I was all alone in the apartment because his mom was supposed to be working a double shift at the hospital where she worked in the Intensive Care Unit on a swing shift. I always felt a little nervous around Connie because she was unexpectedly attractive for a woman in her forties and had a gravity defying backside that one would expect on a teenaged cheerleader. It was all I could do to keep my eyes off her happy haunches when she was dishing out our dinner and I hoped that Tommy did not suspect I had a thing for his mom.

Apparently, Tommy’s dad had gone out for cigarettes one morning and never returned to his less than happy home. The way he told it, his dad was a musician and needed to spread his wings and break out of the married life prison he hated with all his heart. I noticed that Connie elected to not discuss her former husband but I noticed she had a picture of him and his guitar on the dresser in her bedroom and she always changed the subject whenever his name came up. Lately, she had seemed a bit down, but I put that to her breaking up with Carlos the paramedic that delivered the accident cases into the hospital for emergency tending.

Carlos was a real prick and I mean that just the way it sounds. He must have had a thing against women because he was about as rude and nasty to all females as anyone I ever met. It was so strange to see him with the sensitive and caring Connie because she was the kind of person that would go out of her way to help anyone in need.


About six months previous, I had been using Tommy’s computer to do some research and his mom came in with Carlos and they headed straight to her bedroom with hardly a word of greeting. Right after that, I started to hear the unmistakable sounds of a female getting her ass whacked with dreadful enthusiasm. Poor Connie’s sobs were real and concerned me something terrible for the condition of her reddened bottom. Then the noise stopped and the sound of the bedposts hitting into the plaster gave me sufficient evidence that she was getting it hard and heavy and there were no protests of a verbal nature from her mouth. I figured that was a good thing because she was a healthy woman and needed to get it on every now and then. I just wished it was someone other than the nasty Carlos who had a reputation of sodomizing new nurses just to introduce him in a way that they would never forget. I doubted there was a single nurse that hadn’t taken it up the ass from Carlos because it was like some sort of initiation or ticket that had to be punched before joining the team.

I tried to picture the attractive Connie sweating under his weight on her flanks and her pretty face all tear-streaked from her humiliation at his coarse hands and demanding fingers. I pretended to be totally engrossed in my work at the computer when they came out of the room.

Connie was putting her hair back into a tightly banded pony tail and asked me,

“Did you want anything to eat, honey? I got the left-over pizza that Tommy brought home from the shop yesterday. I can heat it up for you in a jiff.”

I nodded my head, not looking at the sour-faced Carlos. He was reported to be a member of a local gang, but kept that side of his life private away from the hospital and I had no interest in finding anything about it at all.

A few minutes later, he left us alone and I could hear the sound of his motorcycle revving up in the alley behind the apartment building. Connie looked at me and I could see the shame in her eyes. We didn’t mention her spanking and her obvious ass packing that Carlos had given her right in the middle of the day. She stood behind me and massaged my shoulders as I ate the pizza and I could feel the soft lingering touch of her tempting torso against my back like a dream of unrequited desire sought but never found.


I was just getting started with Miss November pictured with her pretty blonde head down and her perfect heart-shaped ass up high when Connie walked into the bedroom and saw me naked from the waist down with all those “Playboy” photos spread from one end of the bed to the other. Of course, she was just as startled as I and we both just froze up and stared at each other like we were seeing each other for the first time. Strangely, my cock got stiffer instead of wilting and I think it was because she was standing in the doorway with the sunlight behind her outlining every strand of pussy hair between her long slender legs with great clarity.

“I am so sorry, Harry, I thought you were still asleep. Miss November is Tommy’s favorite also. He has a thing for her. I wished I looked more like her but I am too short and my boobs are way too small.”

Her talk about boobs made me want to get her down on all fours and looking over her shoulder so I could see the reflection of lust in her eyes daring me to go all the way and forget she was my best friend’s mother.

I walked over to her and led her by the hand to the bed and told her,

“Down on all fours and I will pretend you are Miss November. By the way, your boobs are just the right size for me.”

She took up my favorite “all fours” position and proved to be super wet in anticipation of my rampant cock riding straight up her pretty slit from behind. It was like a budding flower opening for the morning dew and she looked over her should with her mouth all scrunched up into a perfect little circle of pleasure that made drive all the way inside until I bottomed out and heard my muscular legs slap into her perfectly curved cheeks. After that, I lost all sense of time or reason. I was so involved with accelerating my pounding until my floodgates could open and relieve me of the pressure of unwanted abstinence from the thing that occupied every conscious thought in my teenaged mind.

“Oh, Mrs. Brown, you have a lovely body. You look like one of the cheerleaders down at the high school. That’s right, come on back and we can get there a lot quicker if you roll your hips a little and whimper like you don’t want it.”

Connie smiled and followed my instructions to the letter. I had to give her an “A” for attention to detail. It was shortly later that my haste to conclude our first coupling led to my spurting of copious streams of creamy cum deep inside her tight entryway and she slowly sank down to the mattress with me still sticking to her like glue not wanting to be deprived of joyful residence. We were like one person and that was all right with me. I really felt quite different than with any young chick I had banged just as a lark to see how tight she was or if she would show me a trick or two I hadn’t seen before. My best friend’s mom was like a safe harbor for me to find my mooring and once tied to her in this manner, I had no desire to cast off anchor for any other port every again.

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