I Find the Pot of Gold
Right after I started my sophomore year, my fraternity decided to go to one of the hot clubs in South Beach. The club had the usual mix of gays, straights (men and women), bisexuals, transsexuals, and transvestites. It was a real freak show and I was certainly not out of place there. I danced with my fraternity pals, got fondled a bit in the crowd, and ended up fucking a bisexual guy in the lady's room while his girlfriend watched and instructed me (and nibbled my tits). Girls were peeking over the stall and cheering as she reached under and stuck a finger in my butt, then stuck it in her boyfriend's mouth to suck. One girl climbed over and started to suck my buttfuck's cock. His girlfriend got bent out of shape and made her leave. Eventually, I came in his mouth and walked back toward the dance floor.
This nice looking guy, about mid-thirties, was watching a girl dance and walked right into me. He was very embarrassed and offered to buy me a drink to make it up to me. We hit it off immediately and had a couple of drinks (yes, I was underage). He told me his name was Rod and I told him I had several friends with the same name. I was drinking White Russians and he told me he had never had one. I told him I loved to taste White Russians and feel the cream run down my throat. I saw a bulge growing in his pants and told him that I thought there was something alive in his pants. He got very embarrassed - it was just adorable.
He told me that he had just moved to Miami from New York to run the Miami office of a major investment banking firm. His office managed the South and Central American territories as well as South Florida. They were very involved in dotcom IPOs. At that point I was far more interested in his dick going up than the NASDAQ index. I asked him if he had ever stuck a large amount in Fannie Mae and his cock grew even larger. The double entendres were getting him hot and he finally asked if I wanted to put my money where my mouth was. I whispered in his ear "I'd like to put your dick where my mouth is." He almost sprayed his shorts. He asked if I would like to come back to his waterfront townhouse and I quickly accepted. It wasn't until I got in the car with him that I started to wonder whether he knew I was a tgirl. He leaned over and kissed me, fondling my breast and I quickly forgot all about telling him.
We pulled out of the parking lot in his Mercedes convertible and headed toward his place. I leaned over and nibbled his ear, fondling his johnson at the same time. It was an impressive bulge and I wanted to free it from its constraints, so I unzipped him and worked it out. It stood high and proud in the night air and I started to stroke it to full attention. It finally stopped growing at about eight inches and I leaned over and licked the head. He moaned deeply and pushed the head into my mouth. My red lips worked up and down his shaft for about a minute, then swallowed him all the way. That was all he could take and he blasted my mouth with his sticky cum. I swallowed it all and he thanked me profusely. The rest of the way to his house, I kept my head in his lap and his cock in my mouth as it dripped cum. He stroked my hair and said sweet things as his cock began to harden again.
We pulled into his garage and went inside his beautiful townhouse. The view was beautiful and the upstairs terrace was surprisingly private. He opened a bottle of Caymus Special Selection cabernet and I knew enough about wine to recognize that he was trying to impress me. I lay back on a cushy chaise lounge on the terrace and sipped the luscious wine as he rubbed my shoulders. He leaned over and kissed me intensely and I moved his hand to my breast. He removed my top and began to caress my breasts and suck my hard nipples. I pulled him back up and opened his fly to get at his sweet cock. I moved him behind my head and had him lean over so I could take it into my mouth as his balls dangled against my nose. The aroma was intense and musky. He lasted longer this time and started to moan loudly as his orgasm approached. Just before he came I put the head in my wine glass and he shot a torrent of cockjuice into my remaining wine. When he finished, I sucked him dry, then drank the wine with his cum swirling in the glass. He looked on in amazement and said "You are the sexiest woman I have ever seen. I'm going to give your pussy my special oral treatment." I started to panic again realizing that he really did not know.
I really have to tell you something." I said urgently as he pulled my skirt down. My cock was tucked between my legs and he had a baffled look on his face as he stared at my pubic area. He spread my legs and I braced myself for an angry reaction. My big cock sprang up and he slipped off the chair and landed on his bare butt. "What the fuck is that?" he asked in a stunned voice. "At least he isn't hitting me." I thought to myself. "What kind of girl are you?" he asked, though he already knew. "I don't believe it, a real live shemale. The ones in the films are so ugly, but you are gorgeous." "Ah ha" I thought, "He watches shemale films." Suddenly it occurred to me, "He wouldn't have been in that club if he hadn't been interested in the wild side of life." I asked him whether he wanted to continue and he told me that he was a bit freaked out. He said he had never had sex with a shemale or a male but had watched a couple of shemale films out of curiosity.
I told him I would call a cab if he wanted to stop. He glanced at my empty wine glass and smiled. He got up and brought more wine, filling my glass and telling me that he would be happy to add cream later if I wanted more. I licked my lips and slipped a condom on him. I told him I wanted him get on top of me and mount me like a woman. I raised my legs and spread them, giving him easy access to my ass. He got some lube and inserted a finger in my ass. As he stroked my butt with his finger, his other hand moved cautiously to my cock, rubbing it carefully. Next he rubbed my balls tentatively, like a child with a new toy. I begged him to stop teasing me and give me an assfull of cock. He slid between my legs and guided his cock to my tight entrance. I told him to prong my ass good and he eased the head inside. It felt so good as it started to slide up my chute, making my cock tingle and my nipples harden. I squeezed his shaft with my butt muscles and he moaned like he was in pain. He placed his lips on my nipple and sucked me gently as he smoothly stroked my ass. He rubbed my other breast, then squeezed it gently, fucking me in a deep, intense way. When he started to cum, I ripped off the condom and swallowed his cock, taking his load in my mouth and purring. Then I drank more of the fabulous cabernet and swirled the cum and wine together in my mouth. He surprised me by kissing me and tasting the sweet mixture of cum and wine.
He had just had his third orgasm and he was a bit winded. He lay on another chaise and caught his breath and I lay beside him, taking his cock in my hot mouth, sucking very softly, getting the last few drops of cum. My cock was near his face and he started to touch it again, studying it carefully as it grew long and hard. I moaned and he licked the head very carefully, as if he was afraid he would break it. I think he was working up the courage to cross that threshold and, finally, he took my cock in his mouth. After a bit of trial and error (and some painful nicks with his teeth), he started to figure it out. He couldn't take more than half, but my moans guided him in his quest to improve his oral skills. He really went at it and soon I was ready to blast off. I told him I was about to cum and he grabbed a wine glass and stuck my cock in just as I shot a huge load. I really filled the glass with cum as he stroked my shaft, milking more juice into the glass. He poured more wine in the glass then offered it to me. I was a bit disappointed, but drank about half. He redeemed himself by drinking the rest and licking his lips. He smiled and said simply, "Thank you my love, it was wonderful and enlightening."
He invited me to spend the night and I gladly accepted. His bedroom was gorgeous and we both fell asleep quickly, in the spoon position with his arm draped over me. About 3 AM I awoke to feel his hard cock rubbing my naked ass. I grinned and asked if there was something he wanted. "Please" he begged, "I need to feel it again." I got a condom on him and slid back in the spoon position. I raised my top leg and he helped me hold it up as he slid his big log back up my asscunt. I rubbed my nipples and stroked my cock as he got into a steady rhythm, riding my butt and stretching my tight tunnel. Finally he blasted a load up my ass, then slipped off the condom and started to toss it. I grabbed it and drained it into my mouth, swallowing most of it. Then I stuck my tongue inside it and got the rest.
I leaned over and kissed him and he grinned. "That was so hot, baby. You are amazing." "Thanks lover." I replied and turned over to get some sleep. "Sweetie, are you awake?" he asked and I turned to see what he wanted. He told me that he had been watching me as he fucked me and was very curious about it. I knew where this was headed and I got very excited. He finally worked up the courage to ask me to fuck his virgin ass and I agreed, quickly. I got him on his knees and lubed him and a fresh condom. I worked a finger in his ass and he started having second thoughts. I assured him I would go slow and eventually worked the head of my cock past his tight assring. He started to panic and I leaned over, rubbing my big tits across his back, then reaching around to stroke his cock. Amazingly, it started to get hard again, just minutes after his fourth orgasm of the night. Very impressive.
I worked it in slowly and he finally started to get more comfortable. I wanted to give it to him harder, but I knew better. Eventually, I picked up the pace, getting into a good rhythm, slow but steady. He was hurting, but loving the way it filled him and the feel of my hand stroking his dick. He wanted to see my face so we flipped over and he straddled me, sliding down my big rod and fucking himself quickly. He started bouncing rapidly and stroking his cock hard, then leaned forward to kiss me and rub my nipples. I was really ready to shoot and he told me to shoot it on his cock. I slipped out and turned to spray his cock and balls with my hot jizz. After I covered his package with my cream, I went down on him and swallowed his cock, eating my cum. Shortly after, he deposited another creamy treat down my throat and kissed me to get a taste.
About 9 AM, I awoke to a kiss and breakfast in bed. He made wonderful omelets with croissants, bacon, marmalade, and amaretto coffee. While I ate, he washed my feet and massaged them with ginseng oil. Next, he sucked my toes, giving me a major hardon. He asked how I liked the coffee and I asked for some cream. He started to move toward the kitchen and I told him I would rather get mine fresh from the source. He grinned and crawled up to my face where I slipped his cock out of his briefs. I covered it with marmalade and pounced on it, sucking him really hard and tasting the sweet gelatin on his cock. I bobbed rapidly up and down till his moan grew louder and I knew it was about to explode. I pulled it out and aimed it at my coffee cup where he erupted with a massive load. I don't know how he had that much after the previous night. I stirred it in the coffee and sipped it, licking my lips and kissing him.
After I finished the coffee, I went to shower and get cleaned up. His shower was huge and had a porthole with a view of the water. I was really enjoying the warm water cascading off my face and over my tits. Suddenly, I felt a pair of hands on my ass and smiled, knowing what was coming next. I leaned forward, placing my hands on the wall and spreading my legs. I reached back and put soapy water in my ass and on his condom-covered cock. He entered me slowly and gave me a lovely morning ass fucking, ending it with another luscious load of cock nectar. I hugged him and rubbed my soapy body against him, my tits caressing his chest and my cock rubbing his tight tummy. He groaned and hissed "Fuck me again. I need my ass fucked again. Please give it to me." I was happy to oblige and slipped on a rubber. He assumed the position, and I rode his ass to a mind-blowing orgasm.
He and I became regular sex partners and he invited me to move in with him. I told him that it was important to me to get a degree and declined his offer. However, I did allow him to help me with financial advice. Eventually he helped me use some of my college money to invest and managed to get me in on some of the IPOs his company was doing. My $5000 initial investment quadrupled with the first IPO (thanks to the internet boom). Then we did several more and each time my return was unbelievable. It doesn't take long to build a huge amount of money with that kind of return. By the seventh IPO, I had over $12 million dollars and he told me to stop and smell the roses. He knew that the gravy train was going to end and he didn't want me to lose my money. Even now, he manages my money and it has grown to over $14 million under his expert handling.
After a couple of years in Miami, he was promoted and transferred back to Wall Street. Fortunately he was visiting me when the Trade Centers fell. He said I was his good luck charm and I know that he was mine. He gave me passion and friendship, a love of fine wines, and financial freedom. Whenever he is in town or I am in New York, I clear my calendar for him. It may be hard to believe, but I am far more grateful for the love and friendship than the money. Rod is a special man.
If you or someone you know has been with Tess, please email me at twonight@excite.com and tell me about it. I am very interested to compare your account with her journal entries.
Check out my fiction stories too (The Awakening, Black Dorm, Star Cruiser, and Olympiad), and my own true story (Shocking Encounter).