Poor Rob

by Just Plain Bob

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, Cheating, Slow, .

Desc: Sex Story: He had the worst luck when it came to the ladies.

There were times when it sucked to be me and in the last three years those times had been too damned frequent. As I sat at the bar in my favorite night spot and nursed my beer I did have to admit to myself that I brought a lot of those times down on me on my own. I seemed to have the world's best AND worst taste in women. Best because I always seemed to come up with the great looking ones; the ones with personality to spare and who were fun loving and a joy to be with and who usually grabbed my heart. Worst because they all seemed to have a hidden flaw - they were all round-heeled sluts. Well, maybe that is being a little bit harsh, but they all did leave me for someone else. But usually not until I caught them "sharing." I remembered each and every one of them and as I looked down into my beer glass the memories came back again.

The first one was Diane. I met Diane on my second day at my new job at the XYZ Corporation. I was sitting at a table in the company cafeteria eating my lunch when someone bumped into my chair and I suddenly had a lap full of meatloaf and gravy. "Oh my God, I am so sorry" I heard as I stood and turned to find an absolutely gorgeous redhead standing there with a hand covering her mouth and looking mortified. I grabbed some napkins and did my best to wipe the mess off me and while I was doing that I did notice that the hand covering the redhead's mouth was her left and that there were no rings on it.

One of the kitchen help hurried up with a mop and some rags and I moved out of the way to let him do the clean-up. The redhead was saying:

"I'm so sorry. I can be so clumsy at times. Bring me the bill for the dry cleaning. I'm so sorry."

"No harm done. It was an accident and they happen all the time. Where do I find you and who do I ask for when I get the dry cleaning bill?"

"My name is Diane and I work in Accounting."

I introduced myself and then excused myself so I could hurry to the men's room where I could get some paper towels and do a better job of cleaning up than I was able to do with the napkins.

The next morning I went to Accounting and found Diane. "The dirty clothes will go in with the other dirty clothes and trying to separate out what got soiled yesterday would be silly, but I don't think you should get away without having to make some form of restitution. I propose that he matter be taken care of by your having dinner with me some night this week."

"That's letting me off cheap isn't it?"

"What can I say; I'm a compassionate guy."

"I accept. When?"


"Can't. Previous engagement."

"Then you need to choose the time. All my nights are free, but only you know which nights you are."

"Tonight would work for me."


I made arrangements to pick her up at her place and got back to work.

I took Diane to dinner and then to one of my favorite lounges. We talked and got to know each other a little better. By the time I took her home I was smitten. Besides being drop dead gorgeous she was intelligent, witty and had a great sense of humor. I walked her to her door and she said to me:

"I had a good time Rob. I enjoyed your company very much." She reached up and touched my cheek and said, "I never kiss on the first date and rarely on the second, but in your case I might make an exception to the second date rule. Call me" and then she went into her apartment, closed the door and left me standing there feeling like I had just won the lottery.

I did call and I did get kissed on the second date and the second date led to a third, fourth and fifth. The kisses got hotter and lasted longer. I'd never gone five dates with a girl before without making a move to get in her pants by the third date, but with Diane I kept my hands to myself. She was the one! She was the woman I wanted to spend the rest of my life with and so I behaved myself.

I showed up at her door for our sixth date and she invited me in. "I decided I wanted to stay in tonight so I fixed dinner for us. I hope you like Italian."

"I do indeed" I said as she led me to the kitchen/dining room area of the apartment. She handed me a glass of Chianti and then fed me Linguini Alfredo with garlic bread and more Chianti while we talked. When we finished eating she asked me if I was ready for dessert and when I said yes she said, "Good, I'll be right back" and she got up from the table and headed for the living room. When she came back into the kitchen she was naked except for a pair of "Come Fuck Me" high heeled pumps. My jaw dropped and she smiled and asked:

"You like?"

I sat there and stared at her speechless and she said, "Not the response I was looking for. I expected you to knock over the table and chairs in your hurry to get to me."

I might have been stunned, but I wasn't stupid so I pushed back my chair and stood up. My hands were undoing my tie as I moved toward her and she smiled at me, turned, and headed for her bedroom. Diane got on her bed, laid back, spread her legs and started rubbing her pussy as she watched me undress. Her pussy glistened with dampness and her nipples were hard and poked up from her breasts. When my last piece of clothing hit the floor she got on her hands and knees and moved to the edge of the bed and as I walked up to her she reached out, took hold of my cock and pulled it to her mouth.

It felt like I had put it in a furnace.

My hands went to her head and I stood there for several minutes rocking back and forth as she devoured me. I was in ecstasy. And then I couldn't take it anymore and I moaned as I started to cum. Diane's mouth clamped tight around me and she swallowed what seemed like endless spurts of my sperm.

I was quick to return the favor. I pushed her onto her back, grabbed her ankles and pulled her to me so that her pussy hung slightly over the edge of the bed. I pushed her legs wide, held them above her head and then I buried my face in her pussy and attacked it like a starving man. I licked, nibbled and probed with my tongue and fingers and she moaned and her fingers tangled in my hair as she gripped my head and pulled me tight to her. I found her clit and went to work on it and she moaned loudly and her hips pressed her pussy against my mouth as her body arched up off the bed and her body trembled and shook as a climax took hold of her. She pushed me away and cried:

"Fuck me Rob; please fuck me. I need it lover, I need it bad."

I climbed on the bed and my freshly hardened cock split the lips of her pussy and started sliding in. She pushed her hips up at me and I went in deep. I slowly started working my cock back and forth in her hot tunnel and she moaned:

"Harder lover, harder."

Soon her ass was bouncing on the bed to meet my hard thrusts. "Yes, yes, yes" she moaned as I pounded into her. Her fingernails dug into my back and her legs locked around me as she hugged me to her and had another orgasm. I felt her cunt muscles working on my cock as if they were trying to milk it and I could hold back no longer. I exploded into her and then drove in deep and held myself there until my cock lost its stiffness and then I rolled off of her and collapsed beside her on the bed.

After catching her breath Diane said, "That was yummy baby and well worth the wait. I hope you won't think that I'm a tramp because I came on so strong, but it didn't look like you were going to make a move any time soon and I wanted you. I decided that I'd better push things before one of the other girls made a move on you."

"What other girls?"

"You don't know? You honestly don't know?"

"Know what?"

"Half of the girls in Accounting have their panties in a twist thinking about you."

"Only half?"

"The other half are married, but even so I've seen one or two of the eyeing you."

I didn't know if she was just stroking my ego, but I won't lie; it puffed me up something fierce. That and her saying that she wanted me. I know me and I know what I've got and believe me when I say I'm no great shakes, I'm a decent looking guy and I'm in pretty good shape, but I'm nowhere near being anything special. Hearing Diane say what she did made me feel damned good.

"Dare I hope that you wanting to preempt the field means I can look forward to a long and rewarding relationship?"

"It is a distinct possibility" she said as she ran her hand down my body and started playing with my cock. "Ready for seconds on dessert" she asked.

Since I had started growing as soon as her fingers wrapped around me I said, "Yes indeed I am."

I even had thirds before Diane kissed me goodnight and sent me home. "My neighbors think I'm a good girl and I don't need them seeing a man leaving my apartment in the morning."

That was the start of a period that in high school would have been called 'going steady.' I saw Diane almost every night of the week except Friday and even though I was never allowed to spend the night at her place, she spent quite a few at mine. I asked why we never got together on a Friday and she told me that Friday was the day she visited family. I had a relative or two that I wouldn't expose Diane to so I thought nothing of the fact that she never invited me along to meet them.

Six months went by and I reached the point where I had worked up the courage to propose and I started shopping for a ring. I found one I liked and made sure that I could return it if Diane refused me and on our next evening together I proposed. She said yes and I slid the ring on her finger. When I went home that night I felt like I was walking on air.

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Story tagged with:
Ma/Fa / Consensual / Heterosexual / Cheating / Slow /