There are few things better in this world than giving a women twice your age a taste of your steed. She wants a break from her mundane lifestyle of soccer practice and Hamburger Helper, and you are looking to soak up her years of experience, but more importantly to see if middle-aged women shag the same.
After college, my best friend and I joined different branches of the military. I went Army, and he, being a total psycho, joined the Marines. We met up last Christmas for some Tuesday night beers at our favorite bar back home, on the prowl but not aggressively so. As we sit consuming amongst other friends, our table is approached by a goddess in her early 40s and a nearly 60-year-old used dishrag. We will call the 40-year-old brunette with a body tighter than an Olympic rower Amy, and Amy is a teacher on break with her teacher friends from out of town. Her older friend, the 60-year-old, we will call her Esther, because that represents just how this woman looked — like an Esther. I am polite to Esther, because I understand the rules of the game, but I have my eye on Amy. Amy, however has different plans, and my future with her vanishes as quickly as it appeared when one of our civilian friends takes her to the dance floor. Feeling bummed, I medicate with more booze… but God was looking out for the troops that night.
Amy returns to our table and tells the Marine and myself we need to meet the rest of her friends. That is when I am introduced to Gwen, a 40-year-old tan blonde who resembles a wiser Charlize Theron with a floral wrist tattoo. We hit it off, but I sense the skepticism in her voice: she knows what I’m after and tells me I’m too young for her. I explain that a connection is a connection regardless of whether or not I’m just 24. She tells me she has kids who are only 9 years younger than me, and how she is recently divorced. I’m intrigued, and want to be subjected to her pent up sexual aggression.
We play pool, and as the drinks flow, Gwen tells me how much she loves to suck shaft and how her hotel is conveniently across the street. This is the exact moment I see my Marine buddy begin making out with none other than Esther, the rotten 60-year-old. Mission: Grey Beaver is officially a go. I take him aside and ask if he has completely lost his mind; this woman is old enough to be his mother’s mother! He answers solemnly, “She’s a beautiful woman, and I’m biting the bullet for my fellow servicemen.” He understands the tactics of the situation. Without him getting with Esther, I don’t have a chance with Gwen. I am baffled that he honestly believes Esther, a woman with a scrotum neck and a voice that sounds like she eats lit cigarettes, is in some way attractive. I cannot discourage him, however; I need Gwen.
Last call sounds and Gwen buys me a shot. I know if I drink it, I’ll be pushing rope against her aging nether region all night without a finale, so I give it to my Marine friend who is going to need it much more than I am. As he slugs the Jameson without question, I tell him I’m leaving with Gwen for her hotel. He agrees to meet us there, and as I leave the bar with Gwen, I see him pulling Esther into the ratty one-stall bathroom. I cannot believe my eyes: that is someone’s ancestor he’s about to bend over the sink.
Gwen and I get to the hotel, and some of her friends would not let me into the room. Gwen, unbothered, has a plan B. She takes me to the service staircase, which has large windows overlooking the street. She pushes me against the wall and begins defiling my young temple of a body by biting my neck and talking dirty to me in a way that made me feel violated. She drops to her knees and takes my pants down to my ankles. As soon as my semi-erect chub feels the chill of the winter air trapped in the stairway, she stuffs it down her throat until her nose touches my groin. She begins violently slapping her face off of my lower abdomen while tickling my lower head with her uvula. She gets creative, and reaches up to massage my ass cheeks during her performance — a welcome touch. A short while passes and I am on the verge of passing out, as she’d sucked almost all the blood from my brain into my penis. She stands, takes her pants down over her L.L. Bean boots, and leans over the railing. I start pounding away like a caveman, but I know I will not be able to bust with all this booze clouding my senses.
I enjoy the moment, but when I feel I can no longer push my spaghetti wiener into her 4-decade-old hole, I step back and quit. I pull up my pants, and tell her I have to go. She understands. She tells me I’m a great guy and that I need to find a nice girl; that I should never settle. I just pumped this woman in a staircase and now she’s giving me motherly advice — I love MILFs. I leave the hotel and notice I have about 12 missed calls from the Marine. He was waiting for me outside, and he was disappointed. He explains that after taking Esther to the bathroom, she had a change of heart — apparently trying to slip the fingers to a respectable elderly woman in a dive bar bathroom was not romantic enough for her.
In closing: Marines make the best wingmen, and don’t be afraid to hit on a more experienced woman. They go nuts for the opportunity, and if you are not rewarded with a sloppy beej, they will at least give you an outstanding confidence boost.
God Bless America..