Poor Rob

by Just Plain Bob

Copyright┬ę 2007 by Just Plain Bob

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

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


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.

It was a Monday morning and I was in the basement where the older files were kept - the ones not on computer - and I was behind a row of filing cabinet digging through a drawer looking for a file when three women walked into the area. They had snuck away to take a smoke break. Smoking was not allowed in the building, but it was raining cats and dogs outside so they figured they might be able to get away with smoking in the basement. They stood there puffing away and talking about a party they had been at on Friday night.

I suppose the right thing for me to have done was to let them know I was there, but I was curious. What man hasn't wondered about what women talk about when there are no men around; like when two or three of them go to the bathroom together so I just stayed quiet and listened. They talked about what a good time they'd had; about the selection of music and they joked about the boxed wine that was served. Then one of them said:

"Can you believe that Diane? She was all over Freddy. I honestly thought that she was going to screw him right there in front of everybody."

"If she had it wouldn't have been the first time. She did him in one of the bedrooms at Marie's birthday party and she left the door open. She might as well have charged admission."

"I don't know how she does it. Rob must be the most understanding boyfriend in the world; either that or the dumbest."

"I'll bet he doesn't know."

"How could he not?"

"Freddy is only in town on Fridays. You can hide a lover if you only see him once a week and he isn't even in town the rest of the time."

"She wouldn't do that to Rob, would she? She is going to marry him. Did you see the size of that ring?"

"She's had it on her finger for two weeks now, but she was still at the party with Freddy on Friday night. We've been gone long enough; we'd better get back."

They stubbed out their butts and headed back upstairs to work leaving me to stare after them and pray that they were talking about another Rob and Diane. I could pray all I wanted, but one of the things I knew about myself is that I wasn't a big fan of denial. I didn't want to go to Diane with what I'd heard. A confrontation based on three women gossiping wouldn't be cool. I decided to keep it to myself for a couple of days.

Wednesday I asked Diane to go with me to a play on Friday and got the:

"You know I see my family on Friday Rob."

"Okay, forget the play. Since we are getting married don't you think I should be meeting your family? I'll go with you on Friday."

"Not a good idea Rob. I'm not too keen on my family. You'll notice that I only see them once a week. I'll need to prepare them for you and then I'll need to prepare you for them."

"Well okay, I guess I'll have to go along with your judgment since you know them."

Friday I left work early and I was waiting down the street when Diane pulled out of the parking lot. I followed her to her apartment and parked far enough away not to be noticed, but still be able to see her apartment door. Forty-five minutes later a guy showed up and used a key to let himself in. It was a long night for me. I sat in my car and watched Diane's door until seven the next morning and the guy still hadn't come out when I said, "Fuck it!" and went home.

I disconnected my phone and turned off my cell. I had no contact with Diane over the weekend and I did it for a reason. She had flaunted Freddy in front of her co-workers at that party so I was going to see to it that those same co-workers saw the last act. At work on Monday Diane called me on my extension twice and both times I told her I was too busy to talk to her. The second time I told her I would see her in the cafeteria at lunch.

I was sitting at a table when she came in, went through the line and then came over and sat down opposite me.

"I couldn't get in touch with you over the weekend."

"I was sick so I had the phones turned off so I wouldn't be disturbed."

"Sick? What did you have? The flu or a cold?"

"No, I was just sick over something I found out."

"Something you found out? What was it?"

I reached across the table and took her left hand in mine and held it. "I don't know quite how to say this Diane, but I think that incest is a very bad thing and that someone who would engage in it must be mentally unbalanced. I don't want to have anything to do with someone like that" and before she knew what I was doing I pulled the engagement ring off her finger. It wasn't that hard since I'd bought it too big and we hadn't yet gotten around to having it re-sized. She jerked her hand back, looked at her bare finger and then said:

"I don't understand Rob; what is going on here?"

"You told me that you spend Fridays with your family and since I can't believe that you would lie to me I can only assume that Freddy is family and that makes what you were doing with him in your apartment Friday night incest, right?"

"I don't know what you are talking about Rob."

I told her about what I'd overheard and how I'd spent my Friday night and then I got up, walked over to the trash can and dropped the ring into it. I'd done all my talking loud enough for everyone in the room to hear it and all eyes were on Diane as I walked out of the room.

That wasn't the end of it though. Diane kept trying to get me to talk to her and I finally had to tell her to leave me alone or I would file harassment charges against her and I guess she got the message because she stopped bothering me.

I met Linda at a birthday party for my cousin Ralph. She was fun to talk to and so I asked her for a date and she accepted. She told me up front that she wasn't interested in a long term relationship; that she wanted to have some fun before she got around to settling down. After Diane that sounded good to me.

For the next three months Linda and I saw each other three or four times a week. The sex was fantastic. There wasn't anything she didn't like or wouldn't try at least once. And Lord, was she ever a party animal. Come the week end she always knew where the parties were and she drug me along to them. It wasn't uncommon for us to be at a party where I didn't know another soul except Linda.

One of the things I had to do as part of my job was pull weekend coverage once a month or so. It rotated amongst seven of us. It was my turn in the barrel and I told Linda that I wouldn't be able to take her to the party that was being held at her best friend's house that weekend. She told me that she would make my excuses and see me Sunday night. Friday afternoon one of the guys I rotated with asked me for a favor. He had the duty the next weekend, but something had come up and he needed that weekend off. He asked me if I would swap weekends with him and I said that I would.

I called Linda to let her know I could go to the party with her after all, but I didn't get an answer so I figured that she had gone over to Gail's early to help her set things up. I showed up at Gail's and looked around for Linda but didn't see her so I asked one of the guys that I recognized if he had seen her.

"Oh yeah man. Last I saw of her she was upstairs doing what she does best" he said as he walked away before I could ask him what he meant. I headed up the stairs and when I got to the top I saw a hallway with five doors leading off of it and four of them were open. A quick check showed that there was no one in the rooms with the open doors so I went to the one that was closed. I was just about to knock when I heard a man's voice cry out "Bitch!" I put my ear to the door just in time to hear:

"Oh God, fuck me damn you, fuck me."

It was Linda's voice. I was going to turn away and just leave the party when a voice in the back of my head said, "Don't you want to be sure?" The door wasn't locked and it swung open when I turned the knob and pushed. There in front of me on a bed was a naked Linda and she was being fucked from behind by some guy I'd never seen before. She was facing the door and when it swung open she looked up and her eyes met mine. I stepped back and pulled the door closed and went on home.

I wasn't in my apartment five minutes when the phone rang. Caller ID said the call was from Linda's cell phone so I didn't take the call. I unplugged the phone and turned off my cell, had a stiff drink and then went to bed. "Two for two" I was thinking as I lay there looking up at the ceiling, Diane and now Linda.

The next day I busied myself doing the chores that needed to be done. I cleaned my apartment, did my laundry, washed my car and then settled in to watch the Rockies play the Arizona Diamondbacks. Around four the doorbell rang and I went to the door and found Linda standing there. I stood there looking at her and said. "Yes?"

"You weren't answering your phone so I decided to come over. May I come in?"

"No need. We have nothing to talk about."

"I'm sorry you saw what you did, but you weren't supposed to be there last night."

"But I was there and I did see."

"I told you up front that I wanted to have fun and enjoy myself before I settled down."

"Yes you did and I remembered and that is probably why I didn't scream bad things at you and attack the guy you were with. I expected that some day you would call it quits between us and move on to some one else, but I also expected that you would do me the courtesy of breaking it off with me before you spread for some one else. After yesterday I have to wonder if that isn't what you did on the other nights when I wasn't around. In fact, I've wondered so much about it I've decided that I need to go to the clinic and have myself tested for sexually transmitted diseases."

Her face paled at that and she said, "I'm sorry you have such a low opinion of me. I came over here Rob because I like you a lot and I want to stay friends with you."

"Fine Linda; call me sometime and we can do lunch."

I closed the door in her face and went back to my ball game.

They say that the "third time is a charm" but I wasn't ready for a third time. After Diane and Linda I swore off women for a while. I went three months without talking to a woman unless it was business related or for a necessary personal service like ordering lunch from a waitress. But eventually the male hormones caused my cock to scream out, "Enough with the right hand you klutz - feed me!"

I didn't want a relationship, but I did want to get laid so instead of looking for someone I could ask out on a date I went looking for someone I could pick up.

She looked about my age and she looked hot! Long dark hair and what looked like a magnificent pair of legs. The mirror showed me her front and the face was beautiful and the cleavage I could see was impressive. I slid onto the barstool next to her and she glanced at me with an amused look on her face and I knew what she was thinking.

"Twenty-one stools at the bar and ten of them empty including the six to my right and the four to my left and he sits down next to me. Gee, I wonder why?"

She knew I was going to hit on her so I did. When the bartender came to take my order I told him to give her another of what she was drinking and he looked at her and she gave him a slight nod and he moved off to build the drinks. I turned to her and said:

"Forgive my being so bold, but my daddy always said that free advice wasn't worth spit so I thought I would buy you a drink as payment for asking your advice on something."

She looked at me and said, "Did he not also say that advice from strangers, paid for or not, wasn't worth all that much either?"

"Well, he did say that I should always look for an expert on the subject and as soon as I saw you sitting here I knew you were as close to being an expert as I would be likely to find."

"Me? An expert? And you could tell that just by looking at me sitting here?"

The bartender brought our drinks and when he had moved off I said, "Here is how I see it. A drop dead gorgeous woman like you sitting alone at the bar in a place like this is going to be hit on a lot. That would make you an expert on what I want to know."

"And that is?"

"I have been in a long term relationship that just went belly up. I have been out of the dating scene for quite some time now and I'm nervous about getting back into it. To be brutally honest about it, I wasn't all that good at it when I was still in it. What I wanted to ask you is what are some of the most effective pick-up lines you've heard?"

She looked at me with what I can only call "a coolly appraising and amused gaze" and then she said:

"I would have to say the one you are using on me now is right up there. By the way, my name is Susan."

"Hello Susan, I'm Rob."

"Well tell me this Rob; what did you have in mind? Your place or a motel?"

"My place is close and a lot more comfortable than a motel."

She finished her drink and said, "Should I follow you or will you bring me back for my car later?"

She caught me flat-footed with that. I was hoping to pick her up, but if it happened I thought it would take a while. Trying not to show that she'd caught me off-guard I said:

"Why don't you follow me. That way if you change your mind you can turn off on a side street or just keep on going when we get to my place."

"Why would you think I might do that?"

"You are obviously not a woman who needs to get picked up in bars. You get hit on a lot, but you are not the type who says yes. I'm figuring you said yes to me on a whim and you might re-think things on the drive to my place."

She gave me another one of those amused looks and then said, "Let's go."

I was pleasantly surprised when she was still behind me when we got to my apartment. We were no sooner inside my apartment than she started removing her clothes. She looked at me standing there watching and she said:

"Come on Rob, get with it. We both know what we are here for."

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