I was in Chicago for several days, on a business trip for my husband’s company. I had two main appointments, one on Monday and one on Tuesday; but the latter was changed to Wednesday at the last minute, so I had to stay an extra day.
I flew in on Sunday evening to prepare for my early morning meeting on Monday, which turned out to be quite successful. I made a sale, and had the contract and down payment in hand by early afternoon.
I went back to my downtown hotel, where I stripped and crawled into bed before calling my husband to tell him I’d made the sale. I told him I hadn’t slept well the night before, so I was going to take a nap, and asked him to call me at five so I could eat dinner and get to bed early.
He called right on time, and by six o’clock I’d freshened up and was ready to go to dinner. The hotel dining room wasn’t open on Mondays, but they served a limited menu in the lounge, so I found a table in a corner and ordered a drink while I looked over the menu.
As I was doing so I was surprised to hear a deep baritone voice saying, “Excuse me, Miss, but you look like a former student of mine.” I looked up and was even more surprised to see Mr. Smith (not his real name), my old math teacher from my senior year in high school, standing beside my table.
“Mr. Smith!” I said. “What a surprise! What are you doing here?”
“Well, I’ll be damned,” he said. “It is you. I thought so, but I wasn’t sure.” We shook hands then, and I invited him to sit down.
I soon learned that he was in Chicago to interview for a position at one of the colleges, and in return I told him about my business there. We decided to eat together, and along with the meal he ordered a bottle of wine.
When that bottle was finished he ordered another. I was becoming very mellow after awhile, and I began to think about how I had liked to cock-tease Mr. Smith when I was in his class.
I’d been the oldest girl in my class, turning eighteen in early November, and I couldn’t help but notice how Mr. Smith couldn’t resist sneaking peeks up under the short skirts I wore. Seeing this, I had often allowed my legs to part, giving him a flash of my panties. I really got a kick out of watching him trying not to look, and I had even gone so far as to buy a set of panties that were nearly transparent, to tease him even further. It made me feel as though I had some kind of power over him.
I must have gotten distracted while thinking about this, because I suddenly heard Mr. Smith asking me if I was all right. I nodded and apologized, saying that I had just been thinking about the old days. He laughed, saying, “The old days? What are you, about twenty-eight now?” I nodded. “Well, I’m not so much older,” he went on. “The year you were in my class was my first year out of college, so maybe five years is all that separates us.”
By now we had finished off the wine, and I said I’d better go up to my room. But as I stood up to say good night the effects of the wine made me nearly lose my balance. Mr. Smith quickly reached out to steady me, and then said he would see that I got to my room safely.
Outside my room I opened the door, then turned to thank him. I felt a sudden thrill when he put his hands on my shoulders, saying, “You know, meeting up with you tonight has brought back some of my fondest memories.”
“Yes, for me too,” I replied. Impulsively then, I raised my lips to his and kissed him quickly. His arms encircled me, pulling me tightly to him as the kiss became passionate, sending hot flashes straight to my loins.
When our lips parted we looked into one another’s eyes for a long moment before he said, “I’m sorry, I shouldn’t have done that. But now I have to tell you that I wanted to do that, and more, every day you were in my class.”
Just then a group of men came out of a room down the hall and started walking toward us. “Why don’t you come in for a few minutes,” I said to him, “so we can talk privately.”
In the room we sat on a small sofa, and I boldly asked him just what else he had wanted to do to me back then. He blushed a little. “I have to confess to having been a dirty old man,” he told me. “Peeking up your skirt every chance I got.”
I told him I knew all about it, and had deliberately teased him. I said that seeing him look at me that way had aroused me, and I had often fantasized that I was alone with him and giving him my virginity. I even told him about buying the sheerest panties I could find, so that I could show him my pussy. He said he had noticed that, and marveled at the way my abundant pussy hair had looked even darker than the hair on my head.
“I shouldn’t be telling you this,” he went on, “but you gave me an erection every day. In fact, you still do. I’m married now, you know, and I’ve never wanted to cheat on my wife before, but I haven’t even thought of her since running into you tonight.”
I kissed him tenderly then. “You know, I said, “I love my husband with all my heart, and would never leave him, but he’s not here now, and what he doesn’t know won’t hurt him.”
As he looked into my eyes I took his hand and guided it under my dress to my inner thigh. “I’m not a young student anymore,” I said softly. “And you are no longer my teacher. We are two consenting adults, alone in a hotel room, where only the two of us will know what happens.”
My hand went to his groin then, finding him hard as steel beneath his pants, which were damp where his cock pushed them out. I quickly undid his fly and worked my hand down his undershorts to wrap my fingers around his fat cock, just as his own fingers touched the wet gusset of my panties.
It felt deliciously naughty to be making out with my former teacher. “Oh God, Mr. Smith,” I whispered into his ear, “I want you to fuck me all night long!”
I could feel him trembling as he asked if I’d let him undress me, as he’d dreamed of doing for 10 years now. I said yes, but suggested we move to the bed. I lay across it, shifting this way and that to accommodate him as he unfastened my dress and slipped it off. I held my legs up so he could remove my shoes, then unsnap my garters to peel off my hose. I arched my back to help him as he released the hooks of my bra and slipped it down my arms to gaze at my breasts for a long moment before kissing each of my nipples and telling me how lovely they were.
I waited anxiously for him to remove my panties and take me, but instead he dropped to his knees, pressing his face against my crotch to munch on my cunt through my panties. I grasped his head, pulling him snugly against my pussy as I quickly built to a powerful orgasm. My thighs clamped his head as convulsions racked my body and juice gushed from my slit. I collapsed then, temporarily spent, but I was aware of him tugging my panties down and off before standing up to quickly strip himself.
When he was naked I goggled at his hard cock, which was considerably longer and thicker than my husband’s. I knew that this former teacher of mine was going to really stretch my box if he ever got around to fucking me. Now he was down on his knees again, just staring at my wide-open cunt. “God,” he breathed. “Your pussy is even more beautiful than I remembered it. You have the pinkest, prettiest pussy I’ve ever seen, in any magazine or in real life.”
I finally asked him if he was going to fuck that pussy or just look at it. To encourage him I scooted to the center of the bed and spread my legs even further. He gave a little gasp and knelt between them, his cock just inches from my yearning snatch.
“Do it, Mr. Smith,” I panted. “Do it now, take my cherry.”
“Oh my God!” he moaned, and moved to penetrate me, his cock finding my opening, the huge head pushing its way in. I was so wet and slippery that the whole shaft easily slipped in all the way to his low-hanging balls, which settled in the cleft of my buttocks.
Although obviously excited, he thankfully wasn’t in a hurry to get his rocks off. He fucked me at a leisurely pace, stopping to kiss me, to fondle my breasts and caress my body, then resuming the delicious screwing. I was unbelievably aroused, and I experienced several orgasms while he refrained from coming himself. But after about 20 minutes of penetration his body tensed, and I felt the warm wetness of his semen exploding inside me. Even before he finished coming I felt it trickling out of me and down my ass, to form a big wet spot on the bedsheet.
As we cuddled in post-orgasmic bliss, he said, “God, that was a little kinky, you telling me to take your cherry when I went to fuck you.”
“I told you I had fantasized about that,” I said. “Now I’ve lived out that fantasy.” I smiled at him. “Did I tell you about my other fantasy, Mr. Smith? The one where I suck your cock until you blow a load in my mouth?”
With that I slipped down in the bed and engulfed his limp member, still wet from our recent joining. It was quite a mouthful, even flaccid, and it became hard within 30 seconds. I’m a pretty skilled cocksucker, according to the men I’ve blown, and I always try to do my best to please the man I’m with. There wasn’t any way I could deep-throat a cock as thick as his, but I could handle four or five inches, and I worked the rest of his shaft with my hands. My efforts were rewarded after about five minutes of bobbing and sucking. His body suddenly went rigid, and my mouth was filled with salty-tasting cream, much of which oozed from the corners of my mouth before I could swallow.
When he finished I let his cock slip from my lips, then gazed up at him as I swallowed what remained in my mouth, then licked the last drops from my lips. He pulled me down then, rolling me onto my back, saying, “Now I’m going to eat that pretty little pussy that I drooled over so many times.”
He kissed and licked his way down my body until he reached my dripping snatch. I love having a man go down on me after having already filled my cunt with his come. Mr. Smith did magical things to my fleshy folds and swollen clit, things that soon had me coming in buckets all over his face.
Just when I thought I might go out of my mind, he moved up, slipped his oversized cock inside me once again and fucked me for nearly half an hour. We fell asleep then, but at some point during the night I became aware of him spooning up behind me for a long, lovely, sleepy fuck.
We frolicked in bed until 10 the next morning, when he had to get ready to go to his interview. That interview went very well for him, and we went out that night to celebrate his new job, returning early enough to knock off a couple of good fucks before going to sleep.
On Wednesday I went to my second appointment, which was not as successful as the first, but I didn’t care. Mr. Smith and I had another glorious night before I had to leave the next morning. But since he would now be living in Chicago, I knew I would see him again whenever I went back.
So as it happens, I had two wonderful reunions that week—one with my former teacher, and one with my husband when I got back home.
I really love my life!—Name and address withheld