Dressed So Ch. 04: Tess's Notes Pt. 01

I shifted on the seat and pulled the hem up to my back exposing my tight thong.

"Where is your dick? Did you have surgery?"

I turned to look back at him smiling, "Silly, its still there but I wouldn't want you to see it, at least not now. Please treat me like a woman and fuck me John."

He spread his seed about my tight hole, slipping one moist finger into my butt, than he slipped in a second. My opening was ready and he removed his fingers and positioning his cock, the head pressing lightly, "Are you ready Tess?"

I looked back to his face smiling, "Yes John please fuck me and make me a woman," and he slipped the head inside.

There was a moment of intense pain but I gritted my teeth and told John, "Please wait a moment. I'll be ok, just a second John."

My ass adjusted to his phallus, "Ok now, slow but deeper, a bit more please."

After some slow and painful minutes he was completely inside me and we paused. "You've done this before John?" I panted.

He was atop me and he reached around my back to hold my breasts, "Yes Tess, but with boys, not a beautiful girl like you. Your tits are nice and you feel great on my dick."

"Ok then, fuck me John, fuck me like a man fucks his woman," he began to move out, "OOHHH, but slowly, big boy, oohh that's better John." His cock was only slightly moving within my bum but it was extraordinary.

After a minute the pain disappeared and I told him, "Deeper now John, yes, deeper, fuck my pussy John."

He was so hard and though not as big as some of Cathy's toys he was warm and was deeply fucking me. "Oohh John, I'm going to, ahh, I'm coming John. Oh, oh no, my dress!" I came and John did too, but he stayed inside me.

After we'd rearranged ourselves John asked, "I had fun tonight Tess, can I see you again?"

I considered the question while he drove home. My dress was stained, but with my juice. My bum was sore, and I was leaking John's juice. "John, I enjoyed what you did to my body and I like you, but I'm really a lesbian. Can you understand?"

He kissed me when it pulled into my driveway, "I didn't hurt you did I Tess?"

I turned and touched his cheek, "Only what I'd expected you sweet boy. Thank you for making me a woman. I'll never forget this night." I reached up to kiss my lover.

I didn't see John the rest of that summer as he went off to college in California. His lovemaking was reasonably gentle and I did enjoy being fucked. He was different than loving Cathy. She was soft, and the climax's we shared were powerful. Maybe I'd want another man someday but I wanted more of what Cathy had to give.

2003.3

I hadn't shared my night with John with Cathy, even months later. Each week my body seemed to evolve, my hair was somewhat thicker and my skin softer. My light peach fuzz on my face seemed not to grow. Cathy would inspect my breasts weekly and pass judgment. My weight, as well as my height, hadn't changed since I began the hormones, but my hips had swelled to over 37".

"Your breasts curve very naturally and the areoles are very attractive, at least to this lesbian."

One evening later in March I asked Cathy to use her toy on my bottom, "Could you allow me to understand how a girl is penetrated?"

She looked at me quietly, "Tess, it's natural you're curious about using your passage for sex, but it won't be like what I feel when you're inside me."

We spoke about my request the following week.

"Girls like us sometimes do fuck each other, with toys, but using our bums generally is not considered. It can be pleasurable but care and proper hygiene are essential. Let's plan to make this a special event, just this once. I'll get you a cleaning kit tomorrow and than Saturday night I'll deflower my young lover's bottom, ok? But I won't lick you Tess. It will be different than normal."

I thought I knew what to do, but Saturday I was taught by Cathy to meaning of 'clean'. After two hours of anal douching Cathy had me shower and than dress for the evening. She allowed me to use the Master bedroom to get ready while she put the little one to bed. She had placed a wrapped box on the bed with a note, "I'll enjoy seeing you in this lingerie and the high heels."

Inside were a white lacy bra, a beautiful thong and suspender belt. The taupe hose were very fine and sexy. The sling back black heels were 120mm and would go well with the knee length red dress.

I was dressed and waiting on the sofa when she entered. She was gorgeous but she was dressed in black pants, a white shirt and a pink tie. She settled next to me and we kissed and petted for nearly an hour. I felt her hardness and was excited that she seemed so into the event and leading me toward a new frontier.

"Let's go to the bedroom Tess. I'm ready to fuck you."

"Oh Cathy, please love me, I want your cock inside me."

"Please remove your dress and chemise Tess, but leave the hose and thong on."

Cathy moved to me on the bed after removing her pants, the strap-on prominent. She removed my white bra and licked and kissed my nipples, biting softly and kissing my mouth, "I'm going to rub my body all over you Tess, my cock can wait a bit."

She kissed me again and then slipped down and turned my hips, "I must lube and lick your sweet opening Tess. Can you see how hard I am for you, how stiff my cock is?"

"Yes Cathy, yes please love me, please fuck your girl. I need to feel you inside me."

She moved me to the edge of the bed, "I can better get to your special hole like this dear," she applied lube as she said, "and will be inside you in a moment."

"Tess my cock can only get inside if you're ready, moist, and relaxed. Breathe slowly baby," as she said this she pushed the tip of her cock inside me. It didn't hurt like with John and she took her time to slowly enter me, just a bit and than pausing. Her hands and mouth were on my breasts. It was quite awhile before I realized she had fully penetrated my bum.

"Now how do you feel lover? Is my meat deep enough for you? Can we start fucking or do you want to enjoy this a bit longer?"

I reached for her and pulled her close to my mouth, while feeling the cock slip slightly out of my bottom, "Now I'm ready, fuck me Cathy, fuck me."

Her control of the toy was evident as she stimulated my hole and herself. "Can I started to push into you now Lady, ready for your anal release?"

"Oh yes, please Cathy, fuck me, deep into me, fuck me with your glorious cock!"

"Tess you've pleased me so deeply for all of these months. I wanted to give you something special, this is your gift, my penetration of you, my loving your body, your face, your breasts, your ass," she was peaking and stopped speaking, nor could I as I responded to her cock, my seed powerfully released into my thong.

We quietly kissed and hugged for a while until I fell asleep.

"Tess wake up, you need to be heading home. It's after 1am and your mother will worry."

I stirred and realized the cock was still inside me but she had removed the straps, "Can we do it again Cathy?"

She looked tired, "No Tess, I need to get you home. You can put the dress and heels on, and walk ok?"

I had never returned home in full makeup and heels and she knew this. "Can't I change than leave?"

"No, I'm exhausted and want you to leave for the night, please."

We hugged briefly at the door and she kissed me lightly.

The streets were quiet except for the sound of my heels on the pavement. The walk was interesting since I'd never worn heels this tall nor walked this far in them. It was amazing to feel this comfortable, dressed as I was. I felt liberated from all of the history that was Tracy. My girlfriend had fucked me. I was happy.

2003.4

After the weekend when Cathy penetrated my bottom I found her crying when I came back from school Monday. She felt guilty of violating me. She didn't know that my birthday had passed a week earlier.

"But Cathy I'm of legal age now. You slept with an eighteen-year-old 'girl'. I loved our sex almost as much as I love you."

She said understood but somehow we'd destroyed the relationship. It was in late April when Cathy called and asked me to gather my things and move them home. I thought I was in love with her and that she loved me. The next three months were very difficult at school and at home. I found a simple job in Chicago for the rest of the summer before I entered College and moved out, never to return home other than for a few days at a time.

2003.9

At the University of Chicago I could live openly as a female and the schools policies protected my true gender. I met many other 'girls' and a great group of lesbians. The girls never asked about my gender since I now appeared so feminine. My body and looks, my wardrobe and manner had all been carefully adjusted with Cathy's guidance. It was her ultimate gift.

Waiting for classes to begin the boys were always hitting on me. Offers of dates, and more were common, but slowly they realized I liked the girls better. My roommate was an Asian girl named Kim who was focused on the sciences. We enjoy each others company but didn't share many friends. Early that first month I shared my sexuality with Kim.

"My cousin in Korean has become a girl, but 'she' doesn't pass too well. I would never have guessed you'd began life as a boy Tess. And I won't share this secret, I promise. We were roommates for the four years at Chicago, and though the rumor is 'Fun comes here to die' this isn't completely true, though we did studied very hard.

During the first semester at Chicago I wrote to Cathy often and she occasionally wrote me as well. I tried to see her over the Holiday but she said on the phone she had met someone. Over the next summer I tried again. We spoke on the phone and she shared that after I'd started College she couldn't handle holding me back. She told me there were new people to meet.

2004.1

I visited my parents for only a few days near the holidays but it was difficult with my dad. I returned to the City the day after Christmas. I wasn't lonely on the nearly empty campus since several of the girls had similar issues at home. The second week at a small bistro I met a lovely boy. David was very good-looking and though not effeminate, not macho either. We stayed and talked after my three girlfriends had left. The next day he met me for lunch, and then bought me dinner.

"Can I take you to a special restaurant this Friday Tess?"

David's wealth was apparent from his clothes, car, and personality but he wasn't a snub. "Do you have something lovely to wear Tess?"

I had plenty of beautiful dresses and said yes to his dinner date. After dinner he asked me to spend the night, "David you know I like women right?"

It was persistent and I agreed to spend the night. We slept together and he found my secret a great joy. As a bisexual he'd never worried about sleep with boys and to him I was a girl, and his cock had plenty to give. We sucked each other off that first night. A week later I slept with him again. He enjoyed sucking me and we had some ass play but I wouldn't let me penetrate me.

"David I may allow you inside me at some point but right now I enjoying you as an oral lover, not a stud." He seemed to understand but when he gave me a special toy a week later I realized he would probably enter me very soon. The toy was a glass double-ended dong, about 14 inches long. The note was explicit: "I want to play with this together Tess."

I liked David a lot, but I really didn't see myself with a man. I stayed clear of David for nearly two weeks, until the new term began. I found him waiting for me to return to my dorm one afternoon.

"I'm sorry that my gift caused you this pain Tess. Please forgive me."

We hugged and he kissed me, "Can I take you to dinner Friday evening so that we can move passed my error?"

His apology was what I needed. So I went shopping, with his card, for a new outfit or two. "Please Wow me Tess."

I visited Neiman Marcus and brought back two pairs of Jimmy Choo heels and a McQueen mid-thigh lbd as well as an Armani knee length dress in red. He wanted to spend some money, but he refused my offer to shop with me. We were to dine Downtown so I decided to dress the part. His lovely girlfriend with a clitty, I selected my fine ivory lingerie and nude hose. The salon took me in Friday at 1pm when someone cancelled and I had the stylist change my look and the color a little.

I'd told him we would meet Downtown so I hired a cab. I enjoyed the ride, rather than using the trains.

David was waiting at the door, "My dear Tess, this is a very special surprise. I love the red dress and you're just a vision."

After dinner we traveled to David's apartment in his car. His hands were on my knee, enjoying the silky hose on my legs. Thankfully it was an automatic. I enjoyed teasing the beautiful boy as he tried to drive. I had decided to allow him inside my bum that night. I wondered if the rejected toy would be available? It was quite sexy but the principle was important. I would decide when and how he got me to take him deep inside me.

Arriving at his place David turned on some soft sensual music and served us chilled champagne. At dinner we had been careful to only have a half bottle since I was not yet of age. He brought us the glasses and she sat watching the moonrise over the lake.

I turned toward him flashing my legs, "David, can I spend the night?"

He smiled and kissed me gently, and I asked, "Did you keep the toy? I 'd like you to watch me play with it."

He smiled and stepped to the bedroom returning with the re-wrapped present and a beautiful small glass decanter, "Remember David, I decide who and what enters my body. You will sit over there and I will use the leather chaise."

I walked to him and he handed me the present and the lube. I set them on the side table. Turning I released the zip of my dress and allowed it to fall to the floor. I pulled the clip from my hair and it fell to my back. I slipped off the bra beneath the chemise and settled on the chaise to unwrap the toy. It was unique with bulbous ends and a narrow waist. I picked it up and lightly coated it with the lube. With my right hand I began to caress my breasts. The music was making feel very sexy and I turned my butt toward David while I eased the thong passed my hips exposing my rosebud but holding my clitty in place.

I turned to lye on my back and reached for the toy, grasping it at the mid-point and kissing the smooth end. Positioned near my opening I slipped it slightly inside, but was surprised that due to the tapered shape it entered much deeper than I'd expected causing me to gasp. I played with the toy; letting it slowly go deeper. This was making me uniquely aroused, as my play was also affecting David. He had his cock in is hand. I wanted to try a different angle so I removed the toy and turned to rest on my knees, butt high in the air, and inserted it again. My ass just swallowed the long shaft, at least half its length inside me.

I fucked myself for a bit but then turned to David, "Get that cock over here and put it in me sexy boy."

He didn't wait a moment, but without rushing he stepped closer and slid in my boi pussy. Maybe it was the pre-coitus play but I was crazy horny and his dick was doing the right things to me. I was thinking he could do this to me every day and what's bad about that? Maybe this boy's cock could keep me happy. I liked that he allowed me to control everything. But now I was close and his fucking was bringing on a huge climax. I screamed as he pulled nearly out and than ran deeply in again. I loved being fucked!

"Ohh, Dav, ohh David fuck me! Fuck me, fuck me!" I came and a few strokes in and out later so did David. He filled my pussy with seed and we slumped to the leather, await the strength to move.

When he did he slipped out of me and some seed escaped, but David was clearly not a macho, as he moved down and licked it up, then turned me on again when he pushed his tongue into clean me, deeply. This was no ordinary man.

The End of Part One