My Milkman

In 1980, my son went off to college, so I took a job in Evanston, Illinois. I had a nice house, in a good neighborhood. I also had a milkman named Lou. Lou was a nice man, a little older than I, married, with eight youngsters. He worked for Wanzer Milk Company. I still remember the company’s slogan,”Wanzer on milk is like sterling on silver.” I have no idea why I remember that.
Anyway, Lou was about 5 feet 5 inches tall. My height. He had jet black hair combed back, a small muscular body, and the biggest bulge I ever saw in a pair of work pants. I wanted to see what was causing that bulge.
I had Lou knock on the door, and then come in and go to the refrigerator and stock it with whatever I needed. We would talk a little and then he’d be off. He was very pleasant. He called me “Missy Lila.”
The day I decided to seduce him, I wore high heeled slippers and a silk robe that came just above my knees. Lou came in as usual and knelt down to check what I needed; I was standing by the refrigerator. He was asking how everything was, when I said, “Lou, I feel dizzy.” He stood up and I swooned into his arms.
I took him by surprise, so he basically grabbed me as I fell and twisted so my back was to him, and he lowered the two of us to the floor. I made sure my robe opened fully as we went down so he could see all of me.
He was patting my face saying, “Missy Lila, are you okay?” He got himself out from under me, and was kneeling next to me. He had all of me to enjoy with his eyes, but he didn’t touch me. I thought, “Well, let’s just see what happens now.” I opened my eyes, reached out, putting my arms around him, and kissed him hard.
Lou put his arms around me tightly and kissed me back, also very hard. His hands were moving over my back and ass. That did it for me. I asked him to help me up, took his hand, led him to my bedroom, and fucked him delirious. Okay, that’s not exactly true. I laid down on the bed, and was fucked by a master. No wonder he had eight young at home. When he undid his belt, zipper, and let his pants fall, I saw what caused his bulge.
That man had about a seven inch cock, but it was incredibly thick. I couldn’t wait to have it anywhere he wanted to put it. He got between my legs and started to eat me like a starving man, and in no time at all had me flopping around, cumming hard. He didn’t let me suck him. He pushed me back down, and eased that thick cock slowly into my pussy. I reached down and felt my hole. It was stretched to its limit. The poor skin was pulled incredibly tight. My pussy was so tight around his cock that it acted like a squeegee, wiping the fluid off him as he went in and out. It was a little painful, and what happens to “Missy Lila” when she’s in pain? Fireworks! It was one orgasm after another as he pistoned that hard shaft into me. Finally, after I was happily spent, Lou cried out, and came hard, his monster punishing my pussy.
“I’ve dreamed of doing that to you since you became my customer,” he said as he tried to calm his breathing. “You are the most beautiful woman I have ever met.” No one had said anything like that since my husband. I started to cry.
After that, we had a system. If he were early, we fucked. If he was on time, I sucked his cock, not an easy feat, but fun. If he were late, I gave him a kiss, and sent him off.
One day I was anticipating him arriving, hoping he was early. I was wearing a very thin, see thru nighty that came just above my pussy, my high heeled slippers, and no panties. I might as well worn nothing at all since it was so thin.
There was a knock on the door, it opened, and there was a very handsome, young boy, holding a carrier of milk. I didn’t see any reason to cover myself because there were too many parts to cover, and after what my life had been like, I certainly wasn’t shy about my body. So I asked, “Who are you?” He looked like he was petrified, staring at my breasts and pussy. He stammered, “I’m Jeff. My dad is Lou, the milkman. I’m off from school, so I came with my dad to help him.” “I see,” I said, “How old are you?” He tried so hard to take his eyes off my fun parts, failing miserably. “I’m going to be 17 next month.”
Believe me, I seriously thought about taking this boy’s virginity, but thought better of it. “All right,” I said. I turned toward the refrigerator so he could see my legs and ass, and said, “Put the milk in here, son.” “Yes, ma’am,” he said. When he left, I said, “Tell your dad I’ll see him next time.” I could tell he didn’t want to go. I walked toward the door. The kitchen table was close to him, so I had to turn sideways to get past him. I made sure my breasts dragged against his chest, and my hands slid over his cock. “Excuse me, Jeff. I look forward to seeing you again.” “Me, too!” he breathlessly exclaimed.
As Jeff’s dad pounded me stupid the next time he came over, he said his son couldn’t talk about anything else the rest of the day. “I made him swear he wouldn’t tell his mother. I don’t want to lose you as a customer.” I told him, “When your son turns 18, I’m going to fuck him.” He said, “He’ll love that for sure.”
Lou and I continued the year enjoying each other as often as we could. Sometimes I felt bad for his other customers that he was late to their houses…no I wasn’t. I also continued to tease Jeff mercilessly. Lou would tell me when his son would be helping him. I would wear the absolute thinnest, shortest lingerie when he came over. As he got closer to 18, I started to kiss him when he left. It started as a peck on his cheek, my hand lightly touching his bulge. I allowed him to put his hand and on my breasts. As the date drew nearer, I started slipping my tongue inside his lips, and squeezing his cock. Just before he turned 18 I took his hand and put it on my pussy, and worked his finger into me, I was soaked thinking about him fucking me. I know he didn’t wash that finger all day.
The big day came. After Jeff turned 18, the next time he came over, his dad and I had a plan. Lou dropped his son off to deliver my milk, and then Lou told his son to stay with me since he had to drive off to supposedly get the truck fixed. Lou wasn’t supposed to have his son with him. Jeff didn’t complain about the arrangement. I think he thought he would just get to look at me longer. I told Lou to give us two hours alone before he came back. Lou just did the rest of his route, and I made Jeff a man.
When Jeff came in, I had on light grey thigh high hose, pretty high heeled shoes, and a very small, see thru teddy. I never wore nylons and real heels for him before. I took him to my parlor and sat across from him. I let him see everything I had. I asked him what he wanted to do? He said, “Can I touch you again? You’re the only girl I ever touched like that.” I replied, “Let’s go to the bedroom and I’ll let you do anything you like.”
He was so cute. He sat there dumbstruck. I had to get up and reach my hand out to him. I led him to my bedroom, sat him on the bed, and started to take off his clothes. He just kept looking at my tits and cunt. When I had him naked I just stood there and looked at his cock. I was so glad he had a normal cock. It was about seven inches long, hard as an 18 year old can get, and a nice, normal girth. I couldn’t wait to have it in me. But first things first.
“Jeff?” I said, I want you to put your mouth on my pussy and make me cum before I touch you. Is that okay with you?” “I’ll do anything you want, Miss Lila.” Good boy.
I took off the teddy, and laid down next to Jeff. I had to lead him through each step. He was moving in slow motion, mentally. I said, “Get between my legs, Jeff. Now put your mouth here. Now put your tongue here.” I thought, “Holy smoke, Baby, snap out of it.”
I couldn’t take it, so I just had him come up and slowly put his cock inside of me. “Now move in and out of me.” I said, exasperated. “Jesus, son, the lowest form of life knows how to have sex.” I have to tell you, he was so cute. I just wanted to hug him to death. Finally he got a rhythm that I liked and gave me a little orgasm before he cried out, tears in his eyes, and came inside my pussy. He collapsed on top of me, breathing a whole lot harder than I was.
I just held him tightly, his head on my shoulder. He was trembling, so I covered us with a sheet. Boy did this bring back memories of fucking those freshmen at the fraternities, and our little voyeurs at the drive-in. They were just so damn cute.
After a while, Jeff started moving. I asked, “Are you okay?” He replied, “Thank you so much, Lila (Missy now gone), I had no idea it would feel that good. “You’re welcome, Jeff. I hope we can do that a lot more in the future.” His eyes got big, “You mean it?” “I sure do,” I said, “You were great. I want to do that as much as you want. You can come by anytime you want.”
I told him to stand up. “I’m not done with you yet.” He stood in front of me, I dropped to my knees, took his cock in my mouth and felt it start to grow. I loved that feeling, still do. He stared at me, his cock getting bigger and bigger. I started moving on his cock until it slid into my throat. He let out a moan and twitched, his legs starting to shake. I worked him hard. He was able to last, having just recently cum. I had him moving his cock in my mouth and down my throat as if it were my pussy. My eyes were tearing, my nose started to run, and I started to drool, but I was determined he was going to cum in my throat.
He jerked forward, his cock jamming down my throat, and poured himself into me. He cried out like he was hurt, but I knew he wasn’t, the intensity of my blow job overwhelming him. His legs gave out, so I pushed him toward the bed, his dick coming out of my mouth with a “Pop.”
I had 15 minutes left and I was not going to waste them. Jeff was laying on the bed on his back, his feet on the floor. I jumped up on the bed, straddled my young lover, and sat on his face. “Do I have to tell you what to do now?” I asked. He was clueless. I had my back to his body, grabbed him on either side of his face, told him, “Stick out your tongue,” and fucked him on my own, using his whole face.
I told him, “Steal Daddy’s car and get over here for more lessons. You need them. When I told Lou what happened, the next time he came over to drill me, we laughed our heads off. “That boy’s handsome,” he said, “but he’s dumber than six cans of paint. He’ll make a good actor.”