Robert Ch. 01

Many thanks to tuhahkhan for editing this story.

Eileen is a tall ungainly woman. She is on the thin side, but with overly broad hips, an oversized butt, and no boobs. Or almost no boobs. They are low mounds, with areolas surrounding her, quite prominent, nipples. She has a plain face. Her straight mousy hair is cut at chin level.

Eileen is a very intelligent woman, but had only finished high school. She works as a paralegal. She is very good at it. Her income is sufficient to maintain a middle class lifestyle. Her home is in a Boston suburb a short commute from her job.

Eileen dresses very conservatively for work. Typically a well fitted suit, usually with a skirt. Occasionally she will wear a pantsuit. Her blouses were always high necked. Off work she is also a conservative dresser. She prefers dresses or skirts.

Eileen is friendly, outgoing; but she is not an attractive woman. Until recently she had very little sexual experience. At one time she tried bar scene looking for love or companionship. The results weren't at all satisfactory. A few times she was able to meet someone. But, the guy never called her again once he got her in bed. Eventually she quit drinking, except for a glass of wine with dinner, because it wasn't doing her any good. Eileen is a realist. She does not bullshit herself. She has her fantasies, but she realizes they are exactly that.

Eileen's fantasies are usually about young, well hung studs lying on top of her giving her a hard fuck. She usually masturbates to these illusions. Sometimes she gets the hots for one of the young lawyers at the firm where she works, but she is always careful not to show any outward sign of her dreams. She doesn't have enough experience to imagine any other way than the man on top. She had experienced oral sex a couple of times, but she had been drinking so her memory of the event was hazy. She did not know if she had enjoyed it or not.

By the time she was forty-five years old Eileen had accepted the fact men weren't very interested in her. She thought about trying women, but she didn't feel sexually attracted to them.

Shortly after her fiftieth birthday Eileen met Robert. Or maybe one should say Eileen met Robert again.

Robert had grown up in the same neighborhood as Eileen lived. He had gone off to college and a career. Eileen had only seen him on a couple of occasions since, at the funerals for his parents. Robert's parents had stayed in the neighborhood after their retirement. His father had died about six years before. His mother passed away only four months before.

Eileen was sitting in for the receptionist, while she went out for lunch, when Robert came into the office. He was there to check on some things about his parent's estate. Eileen greeted Robert, she remembered him as a bright child who was always curious about things. She had last seen him at his mother's funeral. She had thought of him as a hunk. He was in her dreams a few times after that.

Robert remembered Eileen very well, while he waited they chatted about their old neighborhood. Robert concluded his business quickly. On his way out he invited Eileen to lunch, so they could talk about the old neighborhood. "I don't know many people there anymore," he said, followed by. "Let's make it on a weekend so you won't have to rush back to work." Eileen agreed, they decided to meet at a restaurant they both liked the following Saturday.

Eileen had Robert in her dreams again that night. She imagined him with a big cock. Her vibrator was the substitute for him as she pumped it into her wet pussy. She could almost feel him lying on top of her.

Saturday Eileen took extra care in dressing wearing a dress just a little bit low cut. She wished she had cleavage to display. She did think she looked good in the dress she chose, even without big boobs. She had thought about wearing a padded bra, but decided against it. She took extra care with her makeup being careful not to use too much. She had no illusions about this being a romantic date. After all Robert was only in his late twenties to her fifty. But she could fantasize. She would carry the memories home, to use in her dreams.

Robert was waiting for her when she arrived at the restaurant. "You look very nice." He told her. He had arranged for a secluded table where, as he put it. "We won't be disturbed by other diners."

Robert:

I'm Robert, not Bob, Rob, or Robby. I'm twenty eight years old. I stand 6' 1" weigh 190. I am well built, not bad in the looks department. I've been told I'm very attractive to women. I must admit I'm seldom lacking female companionship, if I want it. That may be due to the fact I am very well hung, or that I like going down on women. But it may be due to a couple of quirks in my personality. First I am attracted to older women. Second I am attracted to unattractive women.

I usually have two or three affairs going at the same time. Once I found myself dividing my time between five women, but I found it to be a bit too much. I try to be honest with them all.I never imply they are the only ladies in my life. In fact I make it plain they are not.

When I saw Eileen in the lawyer's office I immediately recognized her. After chatting for a while I asked her to lunch. She accepted quickly. We made our arrangements to meet.

I arrived at the restaurant first. A generous tip secured us a nice, secluded table. When Eileen arrived I complimented her on her looks. It wasn't false flattery, it was obvious she had taken extra care when dressing.

We had a very good lunch. I found Eileen to be an interesting person. She was intelligent and well read. She kept up with current events so she could discuss them logically. Our conversation ranged far further than the old neighborhood. But, she also seemed naïve about some things.

After an hour, or so, of conversation with a couple of glasses of wine. I told Eileen, "I have certainly enjoyed our conversation. You are not only attractive, but brainy too." Eileen blushed a little. She thanked me for the compliment. I continued. "I wish we could continue our chat, but I think the restaurant wants their table back."

Eileen's response was. "We can go to my house. I am enjoying myself. It is so seldom I have such interesting conversation."

"Ok," I agreed. "I'll meet you there." I followed Eileen to her house. She drove into her garage. I parked on the street, not quite in front of her house. I didn't want to make it too obvious she had company. She waited for me in the garage. We entered through the kitchen.

"Would you like another glass of wine?" Eileen asked as she showed me into the living room indicating a place on the couch.

"I seldom have more than two glasses, but with such enchanting company I will make an exception." I replied.

Eileen showed a slight blush again. "Thank you Robert, the pleasure is mine."

I sat on the couch. Eileen brought a couple of glasses of wine for us. She sat leaving a space between us. We both turned so we could talk. After fifteen minutes, or so, of talk Eileen offered to show me around the house. It wasn't big but it was very well furnished. I complimented her on it as we returned to the living room.

Eileen said then. "I am really enjoying this afternoon. It is so seldom I get to entertain gentlemen." She went on to ask. "Have you ever married Robert?"

"No," I replied, "Never."

"I would think some young lady would have snared you by now." Eileen had that light blush again.

"Actually Eileen I am not that interested in young ladies." She looked baffled for a moment until I continued. "I am attracted to older women. And to intelligent women."

"Oh." Was all that Eileen said.

"In fact." I continued, "I find you to be very attractive."

Eileen:

'My God,' I thought. 'Can he really mean that?' My emotions were a mess. A thrill ran through me, nervousness too.

"Robert," I said. "Do you really mean it? Please don't toy with me."

Inside, the thoughts racing through my mind were about the stud I dreamed of. My vibrator was a dick, but the man on top was a fantasy.

"I really mean it." He replied. He put his hand behind my shoulders. He gently urged me toward him. Our first kiss was soft and gentle. I found myself moving close to him.

He kissed me again, starting softly but increasingly passionate. Soon our tongues were entwined. His hand was on my breast, kneading it through my dress. When his hand went to my thigh caressing it I knew I had to have him. I needed his cock inside me. I needed him on top of me pumping his manhood into my hot body. My twat was wet, I could feel my juices seeping into my panties.

I stood then, taking his hand I led him to my bedroom.

Robert:

We stood next to Eileen's bed exchanging a hot open mouthed kiss. She stepped back then pulling her dress off. She was not wearing a bra. The mounds on her chest did not require one. I didn't mind, it was all part of what made me want her. Her nipples were firm, erect with lust. She moved close to me started to open my shirt. I opened my belt and pants pushing them down over my hard cock. I kicked them off my feet. We kissed as I caressed her tits. She fumbled with my shirt buttons. We stepped back from each other. I got my shirt and t-shirt off. Eileen sat on the edge of the bed eying my tented shorts. She reached out to me softly stroking my dick through the fabric. Grasping the waistband she pushed them down. I stepped out of them.

Eileen gave a soft gasp when my manhood sprang free. She lay back then, pushing her, surprisingly sexy, silk panties down. I pulled them over her feet, tossed them aside. I lay next to her.

Eileen:

I couldn't believe how forward I was acting. I had practically dragged the man to my bedroom. I had stripped him. When his cock sprang free in front of my face I gasped at its size. It was bigger than anything I had ever had inside me. And I wanted it. I knew it would hurt, but I WANTED IT!

Robert:

I played with Eileen's boobs sucking them, kneading them. I felt her already wet pussy. I pushed my finger past her swollen lips to the hard nubbin of her clit. When I pushed the finger into her I felt how tight she was. She was ready, she didn't need much foreplay. I put her hand on my cock. She stroked it, kissing me passionately.

"Robert it's so big. Please be careful with me." She murmured in my ear.

"Would you rather rub it over your clit?" I asked her.

"No! I want it in me." She rolled over on her back, her legs splayed and her arms reaching for me.

I moved between her legs as she grabbed my manhood. She guided it to her cunt. I pushed into her slowly, watching her face as I did so. Her head was back and her mouth open as I pushed my cock into her tight pussy.

Eileen:

I held up my arms to him. He responded. His body was on mine. Just as in my fantasies. I hugged him tight as his manhood entered me. I had been empty for so long.

'Oh my God it hurts. I want more. I want you lying on me. I want to feel your body rubbing on mine. I want to hold you tight to me as you thrust your hard cock into me.'

When he began to thrust with his magnificent cock. I forgot about the pain, I only wanted to feel him filling me.

Robert:

As I pushed further into her she pulled me down on top of her. She looped her legs over mine. She hugged me tight. She wanted my body on hers. I fucked her slowly, holding myself back so I would not come too soon. I tweaked her nipples. I kissed her fervently. She opened up a little as we fucked, it got easier for her.

I could feel it when she was starting to come. Her hips started thrusting into me. Our kisses were wet, our lips grinding into each other. Eileen held me tight. Her hips raised off the bed. Her orgasm started with a quiver that became shudders as waves of pleasure passed through her. At the height of her orgasm I felt the spasms roaring through my own body, the thrills up my spine. I thrust my cock deep into her, I shot my come into her eager cunt.

Eileen:

'I'm coming, I'm coming.' My body was elated. The waves crashed over me as I felt the heat of his come deep in me. I held him and kissed him and fucked him and fucked for him. I am overcome with the joy of the best orgasm of my life. I never want to let him go.

Robert:

I stayed on top of Eileen as I softened. She held me with her arms tight around me. She didn't want to let me go. After I had softened to the point I couldn't keep it in her any longer I rolled off her. We lay facing, holding each other. Eileen was on an emotional high, she was showering me with kisses.

She kept repeating. "So good, it was so good."

Eventually she calmed down. We lay there cuddling for a while. Eileen propped her head on her elbow. She asked me if I would like something to eat. "It's almost dinner time." She said.

"I'd rather make love to you again." I told her.

"Oh Robert, I want to but I'm so sore I don't know if I can." She replied.

"But you'll like what I want." I told her.

I started kissing her. As I nuzzled her boobs she pulled my head close to her almost like nursing me. I worked my way down her body licking and kissing her. I spread her legs. I moved between them. I saw the tangle of her brown pubic hair, streaked with gray, sitting like a cap over her pussy, enveloping it. The swollen lips of her pussy peeking through. Opening slightly with lust. Showing me a hint of the redness of her womanhood. I licked and kissed her thighs. I ran my tongue around her pussy. I licked the labia. I flattened my tongue, covered her pussy with it as I lapped her wetly.

I lifted my head looking at Eileen. She was looking at me with a wondering expression. She was silent. I lowered my head to her waiting pussy. Her lips were opening for me. As my tongue entered her she gasped, her hips rose from the bed. She opened her legs wider.

I licked her clit. I sucked it. I pushed my tongue into her hole as deep as I could. Then back to her clit. My tongue traveled up and down her swollen lips.

I swung around then so we were head to groin. I did not get on top of her but my hard throbbing cock was right in front of her.

She reached for my manhood, stroked it. She hesitantly put her lips on it. Her mouth opened. Her lips slid down my shaft.

Eileen:

'He's going to do it, he's really going to do it.' I thought as his tongue penetrated the lips of my hot twat. I soared when he licked me and sucked me and licked me some more.

When he swung around. His beautiful cock was right in front of me I wanted to suck him, but I didn't know how. I touched it first, tentatively, then put my lips on it. I kissed the tip of it, loving it, I opened my mouth. I took as much of it as I could. My lips were stretched. My mouth hardy fit over his magnificent manhood.

Robert licked me, sucked me, sent me to heaven. I rode the waves of ecstasy crashing through me as orgasm followed orgasm.

I sucked him harder as I tasted my own juices on his throbbing cock. His hand was in my hair twisting it. holding my head into his dick. It felt good, but he didn't need to hold me there. I gloried in the hardness of him. In the pleasure I was giving him.

Robert:

I licked her and sucked her. I tasted the come I had filled her with. She was wild, bucking her hips. Her legs clasped my head. Her hand pushed me deeper into her hot wet cunt. She was coming almost constantly. Orgasm following orgasm, so close as to seem continuous.

Her mouth was wet on my shaft as she slobbered and moaned with her own pleasure. I shot my come into her when she was at the height of ecstasy. She sucked me until I softened.

I eased her down by licking her labia and thighs. Then I turned around to lay facing her. Her mouth was slack. My come was dribbling from her. "Eileen," I whispered to her. "I want you to swallow." She looked at me blankly. I repeated. "You need to swallow. You need to be complete."

Eileen:

I knew he was telling me to swallow, but my mind wasn't registering it. I was replete, satiated, filled to bursting with pleasure. I tasted his seed in my mouth. I rolled my tongue in it, savoring it. Then I swallowed as he wanted me to. He leaned down and kissed me then, open mouthed with our tongues twisting around each other as we exchanged the juices of our lovemaking.

We lay together for a long time, holding each other. The scent of our lovemaking was strong in the room. I savored it, tasting it on the tip of my tongue. I asked him, after our passion had abated to pleasant satisfaction, if he was hungry. He said he was, a little. I got up, grabbed a robe from the closet. I didn't bother belting it.

In the kitchen I made us each a sandwich. I put some coffee on. I kept touching my pussy as I worked. I felt sore, but so wonderful I couldn't believe it. I went back to the bedroom. I knelt on the bed next to him kissing him. "Supper's ready." I said. He swung his feet off the bed. He stood naked before me. I stared at him mesmerized as He stooped to pick up his shorts and pants.

We walked to the kitchen together with our arms around each other's waist.

Robert:

We sat at the table to eat our sandwiches. Eileen seemed pleased when I refused a glass of wine. I asked for water instead. She cleared the table when we finished eating. She served us coffee, sat with me.

She seemed a bit hesitant, as if she wanted to say something and didn't know how. Finally she started. "Robert I have never in my life felt so good. I haven't had much sexual experience, none of it came close to the pleasure you gave me."

"But you gave me just as much pleasure," I replied. "It goes both ways."

"Can you stay the night?" She blurted out.

"I can," I answered, "but I don't have a razor or toothbrush." I added, "Are you concerned about your neighbors?"

"I have extra razors. You can use my tooth brush. And the neighbors can just mind their own business." Was her answer.

"We need to talk about something." I told Eileen. "I would like to see you again, if you want to see me."

Eileen:

When he said, "I would like to see you again." My heart leapt. Of course I wanted to see him. But then he went on.

"You will not be the only woman in my life. There will always be others." He looked at me calmly waiting for my reaction. "One more, or maybe two."

I was in a turmoil. I wanted to see him again. 'I didn't want to share him. If I didn't share I would never see him. No one had ever made me feel like he did. Why didn't he tell me before he fucked me? I'm glad he didn't. Would I have cared? Oh my God, I wanted him so bad.'

"Robert," I began. "I don't know what to say. It would appear I have a decision to make." But it won't be hard I thought to myself. "You have given me one of the best days of my life. I have no reason to expect even one more day like this one. I will take what you are offering me. I'll be happy you want to make love to an old lady like me."

Robert smiled, he held out his hand to me as he stood, I stood with him. We held each other for a few moments as we kissed softly.

We sat back down at the table. I poured us another cup of coffee. "Robert," I said. "I think I should know what it is I have just agreed to." Robert looked calmly at me again. How could he be so calm when my mind is in a turmoil, my pussy is on fire.

"Eileen there is another woman I have been seeing for a couple of years. There is another I don't see as often, but we do have an ongoing affair. Both of them know they are not the only women in my life. They have known since our first times together. Both of them accept the situation." Robert paused then. When he spoke again it was softly. "I will never deliberately do anything to hurt either of them."