This is a true story, I first met Mark on one of those phone dating lines. We talked for about a couple of weeks. Mark really wanted to meet me, he wanted me to come over dressed. Now, I had been with a few guys but they always came to my apartment. I had never gone out in public before; I dressed completely and was passable, but I was always so nervous I would get caught.
Now a little bit about me: I was 21 when this took place, 5’6″ and I only weighed 128 pounds. I had long shoulder length brown hair, completely smooth. Up to this point I had never done anal. I just played with toys. I was into kissing, touching, some light bondage and light spanking, and oral. The two guys that I had seen before were both older, as I tended to like older guys. Now for Mark, he was in his late 40’s, six foot tall and 200 pounds, and said he was well endowed and thick. He had his own place in the city.
Well, I finally decided to meet with him. After work I took a long hot bubble bath, shaving all over and then taking a hot shower. Putting my bath and body lotion on, then slipping on my lace top, black thigh highs, and matching pink lace garter, with a pink lace bra, and matching string bikini panties. I sat in front of my full length mirror putting on my pink nail polish, then I spent almost the next hour applying my makeup and doing my hair, finishing with bright pink lipstick. I had bought this little black dress for a special occasion. This is it I thought, then I put on my 4 inch hot pink ankle strap heels. I pulled out this little black purse that my ex girlfriend left. I put my makeup and lipstick and my Id in there, just in case I got pulled over. Wow is what I thought when I looked in the mirror, I thought for the first time I do look passable. Ok so I have a half hour to kill before I have to leave, I did a couple of shots trying to calm my nerves. Then grabbed my keys and left.
Arriving at Mark’s house, it was easy to find, and like he said he didn’t really have close neighbors. I parked in the driveway checking my makeup one last time, went to the door and knocked. I could hear him coming to the door and when the door opened I almost turned and ran. I stood there in shock, as it turned out Mark was not his real name; it was my boss.
He said, “Hi, Maggie. Come in.”
He didn’t know it was me. I walked in almost shaking I was so scared. He slid his hands under my arms and around my waist. Pulling me into him, he grabbed my ass as he hugged me.
“Come into the living room, Maggie,” he said as he held my hand leading me into the room. “Would you like some wine?”
“Yes,” is all I could say.
He sat down with two glasses, handing me one.
“Well don’t you look wonderful,” he said.
I took a big sip of wine and said, “Mark, I have something to tell you.”
“What’s that?” he asked?
“I know you’re Mr. Smith. I work in the office, third desk on the right.”
“Well now,” he said, his hand sliding from my knee up my thigh, “this doesn’t change anything, Maggie. You still enjoy all the things you told me, right?”
“Yes,” I said.
One arm sliding behind my back and the other still sliding up and down my stocking clad thigh, he began kissing my cheek then my neck. We made some small talk, by now the shots and the wine had made me relax.
“Why don’t we go upstairs, Maggie?”
“Ok,” I said as he lead me to the stairs.
I went first as his hands were rubbing my thighs and ass. The upstairs had been turned into one large bedroom with a full bath. He walked me to the bed and I climbed up into this huge four poster bed. He had already removed his shirt, and I must say he had a really nice body, not too buff but very toned with a hairy chest. Mr. Smith was a lot bigger than me and he could very easily have man handled me into any position he wanted. There I was on my back as he slid my legs apart, as he lay down on top of me, his weight pressing down on me, looking me in the eye, it hit me again, ‘OMG, he is going to kiss me! My boss is going to kiss me!’ And then our lips met and Mr. Smith kissed me deeply. All I could think is what a good kisser he is.
I was melting under him, his hands roaming over my body as our lips and tongues explored each other’s. He then began kissing my neck. With the sucking feeling on my neck and him between my legs, I found my legs wrapping around his body as I tried to grind my little clit into his growing manhood. Mr. Smith then slowly kissed his way down my body, pushing my little dress up over my bottom. Grabbing my legs behind my knees, he pushed them apart and up towards the head of the bed. He began kissing and sucking on my bare thighs, leaving little hickeys behind He then began kissing my clit through my lace panties; pulling them aside he sucked on my clit, as if it wasn’t hard already, pushing on my legs and lifting my bottom up I felt his tongue as it rimmed my boi pussy, then slowly slipping in. OMG it felt so good the way he ate my ass; he had me moaning in no time. Be as loud as you want Maggie, no one can hear us. He then flipped me over, pulling my panties off. There I was face down, my bottom up as he sucked my clit some more and tongue fucked my pussy.
Mr. Smith then got up and pulled his pants off; he wasn’t kidding, he was at least eight inches and very thick. He lay down next to me pulling me into his arms kissing me some more, then sliding my hand to his semi hard cock. I stroked his cock as I could feel it grow, then he pushed me down. I knew what was expected of me so I gently kissed and licked his shaft and balls. Then slowly taking him into my mouth, I spent forever sucking his cock, trying to please him. He then pulled me up to him, as he kissed me pulling my dress off and tossing it onto the floor.
I straddled him as we kissed grinding into him, then he rolled me over onto my back. He slid down licking my pussy again then coming up he kissed me as I felt his huge hard cock press into me. The feeling was amazing, the pain from stretching and the feeling of him sliding into me. My eyes rolled back as I moaned out loud, everything went blurry, as I felt him take me. He made love to me forever and I came as his body rubbed against my hard clit, covering his belly with my cum. He had rolled me onto my side as he lay behind me, slowly fucking me, then onto my stomach as he lay on top of me, until he finally flipped me back over onto my back and put my legs over his shoulders.
He came as he looked me in the eyes, filling my stretched pussy with his hot cum. We lay there kissing some more then drifting off for a few. I woke to him kissing and touching me, then was again pushed down to make him hard. This time he came in my mouth, I was surprised and disappointed, I was hoping he would fuck me again.
“Let’s get another glass of wine, Maggie.”
He handed me my panties and said, “Just wear these,” as he slid his pants on.
I asked if I could have his shirt as I was chilly and he said yes. We went downstairs and had some wine. He sat in his large chair as I walked around the living room, soon realizing that he was watching my every move. I caught a glimpse of myself in a mirror, my hair all disheveled, wearing this large white button up shirt, pink bra and matching garter and panties, black thigh highs and hot pink heels. I gave him a shy smile as I walked over to the big windows that looked out over the city. Mr. Smith walked up behind me, taking my wine and setting it on the table. He took my hands and placed them onto my ass, having me pull my panties down. There I stood in front of the window, my panties around my ankles like a whore.
“Don’t move them,” he whispered in my ear.
I heard his zipper and then felt his hard cock press against my pussy as he slowly but firmly shoved it all the way in. Now he was fucking me hard, fast, and rough. One hand gripping a fist full of hair, the other stroking my hard clit.
As he fucked me he said, “Cum for me, Maggie. Cum like the little whore you are.”
I came all over the glass. He pulled out then told me to get on my knees and clean up my mess. He stood over me watching as I licked my own orgasm off the glass.
“Such a dirty little slut you are. Back upstairs slut,” he said.
I did as told. When we got into the room he ordered me to lay on my back and hold onto the headboard. I did as told. He then cuffed each wrist to the headboard. He pushed my knees apart and back almost so they were on either side of my head. He then rammed his cock into me, fucking me even harder than downstairs, making me take every inch until he once again filled my ass with his hot cum.
He took the cuffs off my wrists as I cuddled up next to him falling asleep. In the morning I woke around four am. My hand had slid down to his cock; he was so hard. I slid under the covers and started sucking him. Then he pulled me up and laid me on my back as he gently fucked me again. Kissing me deeply as I came on his belly again and he came in my pussy. I then got cleaned up and put my panties and dress back on and drove home.
(Image Source: Peter North Presents)