Like most students, I took odd jobs in college to help pay for my beer, and porn. Since this was before live cams were common, I used to watch anal sex movies pretty much everyday. I always enjoyed fantasizing about tearing into some females’s tight ass with my near eight inch cock at some point? Or better yer, make it a threesome where I can plow my hard cock into two different asses while I watch anal sex from a first hand. . . and first cock viewpoint!

I was getting ready for my senior year and desperate to raise money for my books which are way too fucking expensive for a college student. Fucking bookstore crooks! Anyway, they had a job posting board where you could leave some tear off phone numbers seeking odd jobs and the like. I thought I would inject some levity and put “Sire for Hire” No Odd Job Too Small for Me and see what happened.

Well, it didn’t take long for a couple of gay guys (if that’s your thing cool but, not cool with me) to call wanting to hook up and I nearly thought my plan had backfired big time! Just when I was headed back to take my posting off the wall, the phone rang. On the other line was a woman with a gravely smokers voice wanting to know if I was willing to do some yard work and minor maintenance at her place before her daughter and grand kids came for the weekend. I quickly jotted down her particulars and promised to be at her place mid-morning the following day.

I printed out my trusty MapQuest directions first thing in the morning shortly after taking the opportunity to see anal sex in some of the new anal sex movies I had bought from the back pages of Hustler and Swank magazine. Man, was it ever great to watch anal sex movies when the porn industry converted from VHS to DVD! Talk about some high definition ass pounding! Many masturbation experts of today will never understand having to go to a gas station or sex shop to see anal sex magazines, watch anal sex in seedy arcades and purchase anal sex movies.

After a twenty minute drive or so, I arrived at Maxine’s house and must say was very impressed with the neighborhood. Maxine, or her husband must have done extremely well in the money making department. I was almost embarrassed to park my car in her driveway and hoped it didn’t leak any oil while I worked. I turned the ignition off and then gathered my work gloves ready for action at eight bucks an hour. Woo Hoo!

I went to the door and introduced myself to Maxine. She had a cigarette in one hand and reached out to shake mine with the other. What a broad! Like a dumb ass, I said, nice house and asked what her husband did. Maxine informed me that her husband was one of the leading Proctologists in the nation before he passed away unexpectedly last year. Talk about feeling like a total idiot at this point! Why didn’t I just shut my fucking mouth?

Maxine gave me a tour of her yard and told me to come inside if I need anything to drink or to cool down from the heat. I went about my work thinking about getting some beer with the money and downloading a few anal sex movies as well. Luckily the work wasn’t too demanding as it was crazy hot outside. About halfway through the yard work, I even took my shirt off as it was sopping wet with sweat. When I was on the verge of passing out, I went to the house to get something to drink.

When I go inside, I could hear Maxine crying at the kitchen table. I went up to her and tried my best to console a total stranger. “What’s wrong, Maxine?” She replied, “I thought I was done grieving about my husband but, when you asked about him, I just fell to pieces inside.” “Oh my, I am so sorry!” Now make that a three time total idiot, moron, jackass. I probably deserved all those descriptive terms for being nosy.

“Is there anything, I can do, Maxine?” With that she replied, “Yes, please come and give me a hug.” Maxine embraced my sweaty body firmly and held on, tears flowing for what seemed to be several minutes. Without warning Maxine whispered in my ear, “I want you to fuck me now please.” I pulled back totally taken by surprise. “What?” I couldn’t think of anything else at that point and by then Maxine was taking me by the hand to her expansive bedroom.

We the began kissing and then I laid her back onto the bed. I then spread her toned legs and prepared to taste the oldest woman I had even been with. Maxine pussy was not dry like everyone jokes about older women. Her pussy was incredibly tasty and who doesn’t love someone who keeps it real clean downstairs?! I worked on Maxine’s pussy as she instructed me to finger fuck her ass while I sucked her clit. This seemed like a good deal to me and I slid one finger in her nice warm anal canal.

I knew she needed a release as her tears turned to joy ass I lapped her pussy and by now had two fingers buried deep in Maxine’s ass. Both our bodies were by now, lubed with sweat and pussy juices. My tongue was almost numb when Maxine decided to take control. Her next words changed my life forever and not only was I going to see anal sex first-hand, I was going to watch anal sex and fuck like my favorite anal sex movies!

“Fuck My Ass, Now!” she commanded. Her pussy was so incredibly wet that all I needed to do was rub my cock along her inner thigh and I would have enough lube for my to finally lose my anal virginity. “Fuck Me Hard and You Better Fuck my Ass Good” she demanded. “Fuck Me From Behind Doggy Style Now!” I walked up behind her and pulled my shorts down and my cock out. Maxine reached behind and spread her ass cheeks, inviting my now throbbing dick to her ass.

Slowly, I placed the head of my cock and the entrance to anal sex heaven. I had the head of my cock inside when Maxine pushed back and swallowed me whole. I had never seen anything like this when I watch anal sex movies. “Fuck My Ass Doctor,” Maxine cried! All I had to do was hold steady. Maxine took control of my cock and her ass. She continued to buck back and forth on my cock and I wondered just how much I could take before exploding deep inside her bowels.

My curiosity was short-lived as Maxine told me to lie on my back and she was going to get on top to finish me off. She pushed me back as my still hard cock sprang from her butt. I was now on my back as Maxine got on top engulfing my cock once more in her ass. Holy Fuck was this ever a great angle to watch anal sex or what? As soon as Maxine started to lay back and gyrate her shapely hips, the urge to cum was not going to be denied to either of us. She was playing with her clit and when she came, I thought her ass had cut off my cock. Somehow, I managed to blast off a load of hot cum for the ages deep inside Maxine’s contracting asshole. As we cooled own, she apologized for calling me “Doctor” during the heat of anal sex and everything made sense from that point forward.

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