tagTransgender & CrossdressersDressed So Ch. 06: Tess's Notes Pt. 02

Dressed So Ch. 06: Tess's Notes Pt. 02


Tess' Notes - Part Two

Please find a moment to read the story "Dressed So". The following is the sixth chapter, support to the five parts previously released. This is the continuing collection of notes Tess prepared over a period of years.


2004.8 The summer between my first and second year I worked at the Library helping with various research projects for the post-grads. In late July I was leaving the return desk when a pretty blonde girl stopped me.

"You're Tess right?" she said. "You did some great work on my Persian and Mesopotamian folders."

I had turned and stopped, she was near, I could smell her scent, and look at her eyes. "Thanks, and you are?"

"Oh sorry, my name is Dani, Dani Stock. I'm doing a post-graduate year here. My focus is the art of the Middle-east before the Common Era," she was now a little nervous as I stared and smiled.

"I'm sorry if I've delayed you, Tess," she was turning to move toward the door.

"No, Dani, please stay a moment. I enjoyed the research. My two Art classes have only provided a survey level look at that period. Your request led me to dig passed the easy stuff." I'd reached to touch her wrist as I said this.

She blushed at my flirting, "Would you like to get a coffee Dani?"

So began my second lesbian relationship. Dani and I spent the remaining summer hanging out. About two weeks before the start of term she sat beside me on a park bench in the history Quad and kissed me.

"Wow Dani, I figured you liked girls that first evening. It took you long enough to get your lips on mine. Can I have some more?" In the shade of a tree we kissed for sometime before another student called us out.

"Get a room Lesbos."

I considered my next move, "Dani I have to share something with you. It is important you understand I don't want to push you away."

She reached to hug me close, shifting her hands to my exposed right thigh. I was wearing a pair of torn mini shorts I'd cut from my favorite old jeans. Her hand moved slowly toward my thigh gap.

Dani moved to kiss me again, her fingers near the panel of my shorts, "Dani, I have, uh, I have a pretty large clit, I mean, ahh, I was once a boy," she was kissing me deeply as I tried to speak, her tongue probing my mouth.

"So what Tess, I want my body to be yours dear girl."

I was surprised and I stopped her, quickly rising. "Did you hear me, I'm a girl, but with a, I have a. I have a Penis Dani!"

She was very near, and in a blink her hand slipped up my nearest leg into my shorts, the fingers seeking to discover my sex. "I need you to stop Dani," I said as I moved a bit away.

We returned to her large room and spent that night loving each other. This was a very special night. Dani was the first woman I was with since Cathy. The lovemaking was soft and loving, our tongues and fingers played at all of our openings. I whispered to Dani, "I don't want your mouth or pussy on my clitty, please love me as a woman, tongues and hands. I need your softness so desperately."

I hadn't used the rodeo nor a leg lock position before. Dani had many ways to love me, she turned my imagination loose. We loved each other for hours. Her breasts were perfect and my playing with her nipples could send her off. Her tongue stayed at my butt forever, until I came screaming. She had me wear my thong to control my clitty, but her tapping on my mound brought me off several times that first night.

The next day she said she needed to do an errand. "Please be here when I return, say about 3pm Tess?"

I went to the Library and punched in for two hours. When I returned she wasn't back yet so I decided to shower. I didn't hear her come in ten minutes later. The opening bath door startled me, "Is it you Dani?"

She stepped into the shower but she was wearing a strap-on dildo. I smiled and kissed her, the stiff cock rubbing my thigh.

2005.4 Dani suggested that I come along for her annual gynecological visit. The doctor wasn't too surprised to see two women in the small examine room. "How can I help you two Ladies?"

A week later I had a new hormone regiment that allowed me to maintain my sexual functions. Dani had become comfortable with penetrating my bottom and though she liked my mouth and tongue on her pussy she asked me regularly to fuck her pussy. She wouldn't even consider anal penetration though.

One morning after we'd eaten a simple breakfast she asked, "Do you ever think of having a man to bed, I mean so you can enjoy a warm cock," Dani was always looking to expand her experiences and this idea had been tentatively raised just after the New Year. Now I wanted to ascertain her intent.

Later that afternoon I asked her, "Do you want an additional lover in your bed sweetie? Or are you just testing me?" We were in bed without a plan for the day. I was naked excepting a chemise and she worn a cozy nightgown of brushed back satin.

"Why don't we get dress and go dancing tonight Dani? We can have a simple dinner and than go to the new club just off Campus. If you want to bring a boy home I'll be OK with that."

She looked a bit surprised, "It isn't a test, but I wanted to see how you'd feel being intimate with another dick in bed. I think you'll enjoy sucking cock and I can't provide you with a real one. Maybe it's a kink of mine but I guess I'd like to see a man fucking you. It would be interesting, and different."

I moved closer and pulled down her gown to expose her breasts, while kissing her lightly, "Maybe it would be fun. I haven't been with any man since David." I recalled that I did occasionally wake to a thought of John's cock in my mouth though.

"But you have to be certain the boy you select understands about us and my clitty. We can't stop a big man who is angry or surprised."

So we spent the afternoon planning our outfits and talking about old flames. She wasn't interested in fucking someone else as much as wanting to see me penetrated with a warm cock.

"Dani, you know I'm more into your beauty and your softness. My only wish was that we could afford to shop more. I'd love to see you in stockings and heels, full glamour make up and your hair done. I'm really becoming a lipstick lesbian."

She came to me and we kissed, "Not on my allowance dear. Daddy already feels taxed by the extra year of study. We've got plenty of great outfits Tess."

Later we had a salad and some wine, then started to prepare. Dani was dressed in tight red jeans and tall black heels with a snug black sweater top. Her bra didn't conceal her taut nipples. I wore a skirt that came to my knees, pantyhose since we'd be dancing and luscious white wool top with a princess neckline.

"Are the heels OK, Tess, I mean, they are sexy as hell, but can you stand them all night, and dance as well?"

She hadn't seen me in 110mm heels, something I took for granted. "I'll be fine Dani. You look so sexy, umm, wanna just stay in?"

We weren't in the club ten minutes when a tall handsome guy asked me to dance. "Ok, so long as you'll dance with Dani next." I nodded to my partner.

"Life should be this difficult. Sure thing, my name is Ted, yours?"

"I'm Tess and this is Dani, and we're real close roommates Ted. We share most things, huh Dani?"

She slipped close and held me, "I love Tess fucking me, and her tongue is a delight on my bottom," she tapped my crotch, "and, well her other features too." and then she kissed me deeply.

I saw Ted observing us and he paused, "I'll find a way to see this adventure through girls."

We danced through a set, Ted steered us, and he wasn't shy about his package. "Tess, are you two for real? I feel like I've fallen into a rabbit hole. You both want to be with me tonight?"

I considered how to broach the discussion of my sex when the dancer next to Ted fell backward making him fall toward me. I turned but failed to stop the crash. He landed on the floor but rose quickly, a bit embarrassed, and accidentally grabbed my skirt. It slipped down to my thighs and there he saw more than I'd intended. My hand reached to resettle my outfit as Ted stood, smiling at my blushing cheeks. As the music shifted we began to dance slowly, "I'm sorry, that was an unfortunate introduction to my undies."

He held me closer, "I can't ask much, just understand Dani and me, well we're not a typical couple."

I moved in closer still so that he felt my subtle but still present bump. "She a bit of a voyeur, she wants to watch us fuck Ted." I kissed him while his hands roamed from my bottom to my breasts and his cock stiffened.

I didn't want a problem with this gorgeous male. I took his hand and brought it to my crotch and he looked quickly to my face.

His other hand was on my bum. Sliding down my cleft, he whispered, "So you were born male Tess?"

I didn't disabuse him of his semantic error, "So you'll fuck us Teddy?"

"I'm all in for your deflowering." He simply smiled with our groins moving to the music but I was getting stiff as well.

After dancing for well over two hours we found a cab and headed back to the dorm. We were settled on either side of Ted. Dani reached for Ted's zipper as we drove along, "Oowgh, Tess he's got one a bit bigger then yours."

Ted smiled, "I'm looking forward to sharing Tess and you Dani, but let's wait until we've some privacy."

He looked at me and I decided to be clear, taking his hand and slipped it beneath my A-line skirt, allowing his hand to stroke my soft clitty. "This is for Dani and maybe for you too, big boy?"

We wasted little time once inside, Dani and I slipped to our knees and opened Ted's pants. She took him in her warm mouth first, sucking and licking his length, "Here Tess, he feels wonderful."

She stood and kissed him as I continued to suck him and soon brought him off, "umm, so sweet Dani, have some," as I stood and kissed her, then Ted.

"He's just rogue enough to allow his seed with a kiss. I like this boy Dani."

Ted moved to the sofa as I opened Dani's tight red pants, "This will require some effort, but wait until you see my girlfriend's naked pussy."

"I've always want to fuck a shaved girl, now I get to suck and fuck two in one night!"

I removed my blouse and Dani pulled off her sweater top, "Who gets your cock first Ted," said Dani. "My pussy or Tess' tight hole?" he smiled and looked back to me, hooking his finger.

"Tess, I haven't had of pussy like yours so let's start there, ok Dani?" Now unzipped my skirt hit the floor.

Dani turned my hips while looking at Ted, and simply moved to allow her tongue to soften my hole. "She'll be find now Teddy," she had spread some of his seed on my opening. I slipped my thong aside and she settled his helmet at my opening in reverse cowgirl. I could watch Dani as she moved to the floor beneath us. He was patient, awaiting my signal, but Dani was excited.

"Tess can you push his cock inside you please," she was licking both his shaft and my hole and I allowed my legs to relax and the head entered me. My tall heels help me to control his penetration.

"He's SO Big Dani, oohh, slowly Ted, just let me do the work," I looked over my left shoulder to see Ted with his eye closed and head back. "So tight huh?"

"My what have I been missing? You feel, I mean your pussy feels amazing Tess."

Dani move to my knees and pulled the thong aside to engulf my semi-hard cock, "You look wonderful atop his cock Tess. Now let's fuck this big boy, ok?"

After Ted's rock hard cock had reached the depth of full penetration, I kissed Dani while I got accustom to Ted's size, rolling my hips about while his cock stimulated my insides. Her tongue still tasted of his seed.

"Are you happy we're playing with Ted Dani? I did this for you dear. I like his cock, but I love your pussy."

I'd started to ease upward, then allowed him to push into me. Again slowly, than again, the pace increasing as my body responded. I lifted off of his lap and his cock popped out. I turned to kiss Dani and turned back to Ted just as Dani positioned him at my opening. I immediately dropped to his thighs, enjoying the deeper plunge. Dani was keeping me moist so I just continued to hump his hard cock. We fucked for four or five minute before the stimulation of the large cock caused my climax. I was still coming when Ted tensed and groaned, and I was surprised to see him coming again so quickly.

He shot into my butt and it was amazing, his cock still sliding in and out of my smooth body. "The subtle movements, the warmth, and the tightness brought me off Tess."

"Tess, his seed is oozing from you," as she bent to lick his shaft clean and my dripping hole.

He has still fucking me, "So, ooh Teddy, oohhh, you do like fucking me, filling my bum?"

"Yeah Tess, I do like this, but I don't think I can get off again with Dani as well."

Ted couldn't spend the night so Dani & I showered. "I won't need to do that again Tess. I'm glad he didn't have the stamina for another round, and that he couldn't stay. I need to spend time, just for us dear."

2006.2 By the holidays Dani and I had split. I was too involved in my studies to maintain the relationship and the episode with Ted had not been my idea. I was planning toward a great paying summer internship. I wanted, I mean I needed a wardrobe update.

During the spring term I met a young 'girl' in one of my classes. She was very passable to look at but a mess when she was moving or talking. She wasn't a transvestite except in manner. Patrick was in need of help, but because she looked so beautiful she put many people off. The boys were clearly attracted to her slim body, but she used silicone forms and a ponytail to complete the picture. Her style was more tomboy, than femme. I introduced myself after class during the second week of term.

"Listen Honey, I'm so not into girls, so please don't feel I'm too rude to ask you to keep your distance."

Wow! It took me a month to get passed the bitchy sound off. I watched Patti or Pat, wondering how to get her to trust me. The opportunity came one snowy evening. I was walking across Campus when I saw Patti being pushed about by a guy. I came near and listened before jumping to a conclusion.

"So you couldn't see I wasn't a real girl? That's just great. I finally meet a guy who thinks I'm a girl and he flips when he feels my breast form shift."

"You could have warned me, I mean you were sucking my cock so nice when your tit nearly fell to the snow."

He wasn't going to get violent so I just slowly moved closer and asked, "Pat, are you OK?"

She turned to see me about three steps away. "He's just now LEAVING. Go, now, or I'll kick you in the balls!"

So this began our friendship. Patrick needed a lot of coaching, some advise and a friend. I didn't push too hard. I did get her to my place and eventually helped her with some shopping, and I gave her some shoes and two handbags I didn't use any longer.

When Patti was dressed and properly outfitted she was stunningly beautiful. I would never have suspected her gender origin. I explained that she needed a new name. She agreed but I took us a week to come to Louisa.

"But Tess, please don't work so hard for me. I see the way you look at me, you want me in your bed. Right now I finally look presentable, so please take me out so I can meet some nice men, maybe even a rich man?"

"Louisa, you do look great, and I would love to even just kiss your beautiful lips, but I don't think you're ready to meet men. You have advance in many ways, but your manner is still too tough. Let's just go hang with my girlfriends. Maybe in a week or two you'll be ready for something more, OK?"

We went to a small coffeehouse and I introduced her to three friends; a lesbian named Kali who I'd met from Northwestern, a tranfemme named Emma who was studying Engineering and a femme boy named Stevie. Louisa got on well with everyone and I think that it was a very important step. She said meeting Stevie was revealing, since she clearly wasn't a girl, yet everyone treated her as one.

On the walk to my dorm she asked, "How does that work Tess? I easily look more womanly yet the girls all treated her in a feminine manner."

I just looked at her as we walked together. "She how many steps I need to keep up to your pace and gait? That's just for starters. Stevie doesn't slouch like a skaterboarder when she's sitting. She maintains her face as necessary. You didn't once check yourself with the compact I gave you. If you had, you would have touched up your gorgeous lips after the second cup of coffee Louisa. You don't need to rush this but you need to respect that you're become something new. It takes time, care and constant attention."

She paused and turned to me, then kissed my cheek, "Thanks for being my friend Tess."

"So close to my lips, my heart is racing Louisa. Can you try again, please?"

She understood my joke but swatted my hand away.

"I don't need a lover, I need a girlfriend!"

By term end we spent most of our time together. Louisa applied, almost too late, for the same internship. I went along for support and saw the manager almost fall over herself to hire Louisa.

"Don't you dare try to tell me you haven't learn something's from our lessons Louisa," she was strutting in a 120mm pair of beige pumps.

2007.2 Louisa had changed her major and was slowly moving toward living as a woman fulltime. We still spent a great deal of time together but my focus was on my own academics. I would be graduating in less than 16 months. My major issue with my dear friend was trying to keep her honest. I had no issues passing and Louisa, if possible, had even few issues. She had grown into a near woman. Occasionally she still fell back to 'boy' mode, especially when drinking beer or playing pool.

The boys loved to watch her move about the pool table completing complicated shots her butt bouncing atop her heels. She had become quite a good cocksucker and those few boys she took into her bed, were quiet about her real gender, but she wouldn't share her sexual past and it would blow up on her every once and a while.

"Just stop trying to bed your next hunk Louisa. One of these men is going to punch you or worst."

"But I want someone to love me as I am, don't you see Tess. The hormones have helped, so they don't think I'm a boy. Well except the bold ones who reach up my dress. My clitty is much smaller now, only that guy you introduced me to was really surprised."

"You mean Ted? Even he didn't come to realize you were like me? Thankfully I was still near to calm him. He actually did think you were a girl Louisa, and that's just wrong. You can't do that, please promise me."

"But when I suck them off they ALL like it Tess. I only consider one in ten beddable, Ted almost hit me due to his surprise."

She wouldn't learn this lesson without being abused so I protected her as much as possible. Along the way I realized I wasn't so keen on guys. I liked many of the men I met, as friends and with several did enjoy the sex. But I began to understand that I needed a woman in my life, and Louisa didn't quite fit. Her beauty was more than I could handle. I mean once her breasts were between an A and B cup she could have signed a contract to walk in New York, or even Paris. But that wasn't what Louisa wanted. She wanted a man; a man to take care of her, to love and respect her; little clitty and all.

2008.1 Just before Christmas I was shopping downtown at Nordstrom's for a new pair of heels. I had been with the saleswoman for an hour and a half. I was unaware of someone watching my process due to my focus. When it came time to finally select the single pair I couldn't. Three different shoes were perfect. A black Michael Kors pump, or maybe the beige Choo slingback, but definitely the Louboutin stilettos.

"These decisions are too much to witness. Mira please put these all on my account."

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