Fuckin' Chattin'
There is an old movie where a mob guy dresses as a woman and tells a doctor that he "loves fuckin' chattin". Now I know how he feels. I first discovered the chatroom at Planet-Shemale, then moved to the one at Gay.Com. I discovered that I really enjoyed chatting with horny guys while sitting on someone's cock. I found that with the right computer setup, I could sit on a cock and squirm and still type fairly legibly. I can also get my cock sucked. Now this has become one of my favorite pastimes and my friends enjoy it too. We still have regular sex, but at least twice a week I get fucked and/or sucked while chatting online. The only time I interrupt is to swallow a load of cum. I find it difficult to see the screen or type while a cock is squirting semen in my mouth.
I eventually tried phone sex and videocams, but the phone thing backfired when a guy tracked my number down using a crisscross directory and showed up at my house uninvited. I stopped the videocam, when pictures and videoclips of me showed up on the web.
I did stop chatting for a few months because the private requests became overwhelming. I know that all of you horny boys are just looking for a hot shemale to fuck but I couldn't chat with a guy without getting seven or eight private requests. It got to be too much. The interruptions made it impossible to carry on a conversation. I've now learned a few chatroom tricks which make it easier.
Greek in Greece
My friends who moved to Greece invited me for a visit to their villa on Mykonos. I had been to France, Italy, and most European countries a few times, but never Greece. I had always been intrigued by Greece, since it was the home of Lesbians (Lesbos) and the place where Greek sex was made popular. In olden days, the soldiers were accompanied by young men who were used as a sexual outlet. Those who learned to use their asses to apply pressure to the soldiers' cocks were well rewarded. While this is obviously an outdated practice, it does make me horny thinking about a Greek army unit using my ass for their daily pleasure. Yum!
When we arrived in Mykonos, Marco and Sara greeted Maddie and I warmly and invited us to join them for a swim at a private section of beach below their villa. Clothing disappeared quickly and we were swimming nude in the Aegean Sea. Within minutes Marco's cock was in my mouth and Maddie's was down Sara's throat. Shortly after that, we moved to their living room and condoms and lube appeared. Marco was up my ass in a New York second and Sara had her cunt impaled on my cock. After some maneuvering, Maddie got her cock up Sara's butt and we both drilled her nether region as Marco plowed my inviting tunnel.
After I took Marco's hot load up my ass, Maddie soon replaced his cock in my ass and I shifted to Sara's tight ass. Marco let me suck the last drops of cum from his cock and I kept sucking until he got hard again. He decided to give Maddie's ass a spin and planted his sweet cock balls-deep in her butt. When I came, Sara took my load in her hot mouth, then shared it with me. I rewarded her by going down on her sweet pussy. I worked her clit and tongued her steaming hole until she came, then kept going while she had two more orgasms. Meanwhile, Maddie kept pounding my butt while Marco drilled her slutty hole. They finally reached their limit and I took both their loads within seconds of each other. The next few days were a blur of their horny Greek bisexual friends, all of whom got a taste of my cock or my ass. I highly recommend Mykonos for those who love the bisexual scene.
After we left Greece, Marco and Sara joined us at a villa in the Bellagio area of Lake Como. We rented the villa from a gay American couple who billed themselves as the homos of Lake Como. They greeted us when we arrived and we invited them to join us for dinner at a local restaurant (they were hunks). After dinner and several glasses of Port, we went back to the villa and sat on the terrace, overlooking the lake. Before the evening was over, both of those hunks got to mount me and ride my ass. They both had amazing staying power, fucking my slot over thirty minutes each.
Scott's Yacht
One of my favorite places to have sex is on a large yacht. The motion of the sea is very erotic and you can fuck under the sun or stars without worrying about getting arrested. My friend Scott has a 120 foot yacht with 7 beautiful bedrooms. His first mate, chef and cabin boys are all sexy, horny guys and his friends are some of the most sexually provocative people I have ever met. One of our trips was particularly memorable. I flew to the Bahamas to meet them and we sailed from there down through the islands, finally stopping in St. Barts. Along the way I got to know the other guests. I had brought Maddie and Sandy with me and Scott had one gay couple (Gerry and Patrick), one bisexual couple (Harry and Carla), one single bisexual woman (Paulina) and a tgirl (Millie). Things didn't get interesting for a while, the first day, because everyone was sunning nude. Eventually, however, several of us jumped in the pool and that many naked, horny people in a confined space is bound to lead to sex.
It all started when Gerry and Patrick approached me and both began to stroke my cock under the warm water. Being the shy, reserved young lady that I am (stop laughing), I invited them to taste it. I sat on the edge of the pool and they took turns sucking my shaft and licking my balls. Others were watching and masturbating, when Maddie invited Millie to have a taste of her huge cock. Millie jumped on it with tongue flying. Harry couldn't resist Millie's ass as it wiggled in the water as she sucked Maddie deep.
Harry quickly slipped on a rubber and within seconds had his thick six-incher lodged all the way up her hot love chute. He moaned loudly as Millie pushed her ass back against him. I motioned Paulina over and buried my tongue in her cunt as she stood over me. She screamed in ecstasy as I tongued her clit and cunt. Not to be left out, Sandy and Carla moved into a hot 69 as Scott slipped his luscious, juicy cock up Sandy's butt.
The rest of that day and well into the night, we paired off in various combinations. After dinner, I fucked Horst, the German chef and then let him mount my horny ass as I took turns sucking off the cabin boys (Perry and Max). Perry and Max roomed together and when no visitors were on board, they spent their time fucking each other senseless or getting reamed by Horst. Max told me that one day he was gone ashore overnight and Horst was so horny that he fucked Perry six times and let Perry fuck him three times. Perry said that he had trouble walking the next day. That's my kind of crew.
Scott was the captain of the ship, as well as the owner, so he often had to attend to things on the bridge and could not join us. His first mate, Terry, was a bisexual guy and covered the bridge when Scott was joining the party. Once, during the trip, I noticed that Scott and Terry were nowhere to be found so I walked up to the bridge to check it out. When I arrived and peeked in, Scott had Terry bent over and was fucking him incredibly hard. Terry kept grunting and saying "Slam that cock up my ass babe! Give this whore's cunt the hard fucking it deserves.". I caught Scott's eye and he motioned me over. I slipped on a condom and lubed up. Scott said "Stay there Terry while I get some more lube." As he slipped out, I slipped my cock up Terry's hot, juicy hole and began to pound the hell out of him.
I slowed momentarily to let Scott slip on a fresh rubber and slide up my slot. Then we got a great rhythm going with me getting the best of both worlds. Eventually, Scott said he was ready to shoot and Terry pulled off to get his load. The look on Terry's face was priceless, but he recovered quickly. He slid his hole back down my cock and motioned Scott to feed him his cum. Scott got creative and slid under Terry as Terry went down to his knees. I moved back in and continued to fuck as the two 69ed each other to huge orgasms. Cum dripped everywhere as the guys tried to catch it all. When I pulled out to shoot, both guys got a facial and a mouthful of juice. I licked the excess off of them and sucked the last drops that were still dripping from their spent rods.
Later that night, my bedroom became a revolving door as half the guests stopped by for a late night fuck. By the time we arrived in St. Bart's, I had fucked everyone on the ship and had every cock in my mouth and up my slutty ass. The beaches in St. Barts are clothing optional, but the tgirls in the group still created a stir as we strolled past the naked tourists to a private spot. Guys did double takes and two women licked their lips at our big dicks dangling in the breeze. By the end of the day two couples had wrangled an invite to the ship and that night I managed to get my cock up all of their asses and I wasn't the only one. One of the women was a gorgeous redhead with double D tits a tiny waist, and an ass that caused heads to turn. She shaved her pussy and I must have spent an hour working her into a frenzy. After her fourth orgasm, she begged me to fuck her ass and I happily obliged. When I finished with her, I fucked her husband's ass and shot a load in his mouth, which he shared with her.
As we sailed back to the Bahamas, I decided to move out to the front of the ship and do my "King of the World" imitation from the bow. As I leaned out, I felt a hand on my butt. I looked back and saw Harry and I smiled my most inviting smile. Encouraged, he slid my thong off and slipped his sheath up my ass as he cupped my big tits with his hands. He began to slide in and out of my ass and I purred as the cockhead massaged my prostate, making my cock stand out proudly. About ten minutes later, we began to approach a cruise ship. Scott turned to give the larger ship a wide berth, but the passengers on the port side of the ship got a wonderful view of Harry plowing my butt as my cock waved in the breeze. They were yelling and whistling as we passed, encouraging Harry to "pound that bitch's ass".
Since that trip I have been on three other voyages with Scott, all of which were a sexual free-for-all. Our next trip will be through the Panama Canal. I hope that the guys who work the locks will enjoy seeing me get fucked as we pass through because I intend to give them a show.
My Sexual Legacy
As we went through my journals to gather the information that went into this book, we compiled some statistics. While I'm sure that the totals are not totally accurate, due to my inability to recall all of the details of some of my group sex scenes (even when I did the journal entries the same day), they are probably not far off.
The stats as of August, 2004 are as follows:
Blowjobs given 12,153 Blowjobs received 7,214 Loads swallowed 9,786 Anal received 9,622 Anal given 6,123 Female oral sex given 2,345 Female intercourse given 1,643 Handjobs received 1,987 Handjobs given 2,456 Double penetration received 2,765 Double penetration given 2,178 Total men 3,213 Total women 1,712 Total tgirls 134 Total encounters in clubs 653 Total encounters on beaches 174 Total encounters in cars 1,198 Total times being hit 3 Total times being verbally abused 18 Total white partners 2,622 Total Hispanic partners 1,212 Total black partners 833 Total Asian partners 211 Total mixed-race partners 181
Landmarks where I've been fucked:
Eiffel Tower Empire State Building Staten Island Ferry Central Park Statue of Liberty Carnegie Hall US Capitol Washington Monument Independence Hall Old Faithful Half Dome Golden Gate Bridge Carnelian Room (San Francisco) Grand Canyon (no, that is not another name for my ass) Royal Gorge Yankee Stadium Shea Stadium The Astrodome Pro Player Stadium Orange Bowl The Forum (LA) The Staples Center (LA) Santa Monica Pier The Hollywood Sign Mardi Gras Float Coliseum in Rome Seattle Space Needle The Alamo San Antonio Hemisfair Tower Carlsbad Caverns Sydney Opera House Great Wall of China Mad Ludwig's Castle Red Square in Moscow Tower of London Toronto Tower Toronto Skydome Hotel (at the famous window)
As you can see, I'm an equal opportunity fornicator and I could clearly be classified as a sexual addict. However, I travel the world in private planes and yachts, stay in luxury hotels, eat in the finest restaurants, and have sex with very interesting people and I am almost never depressed. I give money to worthwhile causes and do volunteer work fairly often, something I highly recommend. Keep in mind that this was not my life story, it was a sexual memoir for my life to-date.
I hope this has been entertaining for you. If you got off at any point while reading it then I am pleased. I love to facilitate sexual pleasure any way I can. Many people will be surprised at my life and some will judge me harshly. To them I say, walk a mile in my shoes (or spend some time up my ass) and you would probably see the world differently.
Goodbye and good sex.
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).