Dressed So Ch. 05: Tess' Friend

Shifting to the right side she withdrew the toy and brought it to her mouth. When she was just cleaned she had no issue licking her fluids off of her toys. Again she pressed the toy up but she twisted it slightly as it moved and somehow more of the toy slipped inside. The feeling of fullness was surprising and again she turned onto her tummy, the end of the partially exposed toy dropped to the bed surface. She relished this new feeling for several minutes, the meaty phallus moving about inside her as she shifted slightly. Instead of a pounding fuck her toy was somehow at home deep within her. Again she withdrew the long toy, moistening it with her tongue and moved it inward again, twisting but in the opposite direction and this time most of the toy was trapped by her tight inner cavity. The toy was deep but the end protruded.

"Wow" escaped from her mouth, her surprise so complete. This time when she rolled to her tummy a new sensation was evident. The toy wasn't a vibrator but due to her subtle movement it was stimulating her special places. She realized she was excited enough to climax. It was deep within, if she moved just so and felt the prick, it was fucking her or at least it felt wonderful. She slipped a pillow beneath her tummy, and just moved about, rolling side to side and, boom, she was coming, A deeply felt climax continued for nearly a minute. A moment later she was asleep or maybe passed out.

When I awoke, the phallus was still deep within my boi pussy. Removing the 8 inches buried within me took a few moments and my full attention. It reminded me of the rush of the orgasm. Pausing to consider the intense pleasure I moved to the edge of the high bed still a bit woozy, lowering my heels and went to the Kitchen to cleaned the now very special phallus.

I was still in my sexy outfit when Charles called later that evening, and we talked for well over an hour. I really liked him, how he listened and paused to think when I spoke. We'd planned a lunch meeting for Wednesday near his office off Madison Avenue.

I escaped from the Office a bit after Noon. I walked the short distance in my black pumps. The place Charles had selected wasn't too busy and they were able to talk quietly. He explained his new position at a large accounting firm. He was the director of new clients and had to travel lightly but enjoyed meeting the clients. He had studied Accounting in Boston and completed a Masters in Marketing in Colorado.

"I started at this large firm about three years ago but was transferred from their Miami office a couple of months ago. This is actually the largest office within the firm."

Charles was the second child, born in the Midwest and the family lived in Indiana. I shared my passed but kept to the general rather than the details. He didn't need to know about my difficult teen life.

"I did a few years in a small college outside of Chicago but completed my studies in Brooklyn. I see my career as a means to have an independent life, rather than as a drive to work too much. I like to do well but within a near forty hour work week."

I didn't explain the difficulty of being almost too beautiful, in a City where every guy wanted a quick relationship and sex.

"My interest in dating is to expand my horizons. I need to meet people and I love the social opportunities, but I want to, this may sound a bit weird, but I want to control the situation a bit. Meeting in a bar, or through friends can be ok, but there's a lack of sincerity, a rush to get to the next step in a relationship."

Charles looked at me, "Your plan is a good one Louisa. Patience is important to me as well."

We had a lovely date. I was in my business attire due to an afternoon meeting away from the Office, low heels and a dark grey suit. My long blonde hair was held in a ponytail. Though I was worried I was getting too close he asked me to meet for a drink Friday evening near my apartment.

"I'd like to see you again, sure, Friday evening can work, say after 6pm? Oh, but I have an early morning appointment so can we keep it simple?"

He smiled, "Patience, it works for me."

I was a bit tardy Friday evening and I was excited to see Charles when I arrived. He was standing near the doorway waiting. We relaxed with a bottle of Pinot and shared an appetizer. Charles made me feel comfortable as we talked until past eight but I told him I needed to get some rest. We'd seen each other three times in less than a week.

"Can I walk you home Louisa?" I was tempted to bring him home but I had to hold to my plan. Tess would have been proud. We walked quietly along the stone sidewalk, my heels clicking. When we parted I kissed him deeply, but stopped short as his hand moved across my behind.

"You feel wonderful in my arms Louisa." His hand played across my skirt covered bottom.

He pulled me close enough that I could feel his cock. Could he feel my small bump? I had to slow my responses, it was exciting to be held and kissed by him, but I had to keep focused.

"Goodnight Charles," my hand lingering in his as we parted.

I saw him watching me from the corner, so a turned at the stoop and waved goodbye. The feeling of his awareness of my sex seemed clearer each time we were together.

I'd scheduled my 8:30am dental appointment weeks earlier, so I got off early. When I returned I had a simple lunch. Now what to do? Charles was on my mind, so I decided to try my deep toy again. After bathing I dressed in a soft pastel blue lingerie set and I settled on the bed to try to enter my tight hole. Again I started slow and only inserted about 4 inches. On the next penetration I moved it deeper and then relaxed. Removing it slowly I wondered about Charles cock. Would he enjoy having my bum atop his cock? The final time I pushed and twisted the toy inside I felt the upper tip of the long cock move slightly and then slip in deeper. I almost jumped up to see how much was within me, but I needn't, my fingers proved that the phallus was protruding less then four inches from my tight rosebud. Again with the soft rolling movement I brought myself to an orgasm. I wondered if others were enjoying their toys in the same manner.

Charles called late in the afternoon and asked if I was free Sunday to take a stroll in Central Park. The next day I wore a simple ankle length flowered light dress and flat sandals. We met at the corner of 65th Street near the Zoo and walked for over two hours, flirting and talking, and some light kissing. We stopped at the Boathouse for a glass of wine and some light food and afterward Charles held me close and kissed me deeply. I almost came from the excitement of his lips, his chest pressing my breasts. His hand came to cup my right butt cheek and I allowed the intimacy as he moved lower, holding me closer while we kissed. He suggested we meet for dinner during the week; we would speak in a few days about a plan. I was quite excited, his hardness was distracting and I needed to be careful.

"Charles, I'm very attracted to you and love spending time together. The relationship may be moving quicker than may be prudent. I'm excited to be near you, but, ahh, I want to get home since tomorrow is a work day."

"I completely agree, I love being near you Louisa. Your beauty is intoxicating and I need to know that you feel comfortable. I don't want a superficial relationship but a, I mean I want someone special. I want a serious relationship too. And I'm following your cues, ok?"

Again he watched me but this time from a bit closer to my stoop. I was definitively lusting about his body. The close hug had allowed me to feel his semi-hardness. I almost couldn't believe my boyfriend is so attracted to me. He seemed to understand my pause but I knew I needed to clear the situation Monday.

I awoke early Monday and considered how to broach the subject. It was a work from home day for me and I found starting early was helpful. Around 10am the bell rung. There was a package at the door and I slipped on my low heels and went to collect it. Returning to my apartment I saw the package was from Charles. I opened it to find a beautiful pearl necklace. It was a three strands and about 13" long. My hand went to my throat, wondering if my very small Adam's apple was a give away. I was in shock; I'd receive gifts from lovers but nothing like this. I saw the note and quickly torn the seal. The note was quite long, but in the third part he said he was falling in love with me. As I sat slowly onto my Living Room sofa I read :

"Louisa you are a very special, a very beautiful woman and I want to be with you. I feel you've a secret that you feel is holding us back, but I assure you, nothing you are or were will change my heart. Please consider my heart and share your painful past so I can truly love my new woman."

How could he have found my secret? Was there a mistake I made. Someone was divulging my history on-line? What could I do now? I was in shock and slid down on the cushions and cried until I slept.

When I awoke near 1pm I looked at the package again. He had written his address on the return panel. I went to my Mac and googled the location. He lives on the next block! I ran to the window to check what this implied. Mine was a fourth floor apartment, and his number was #302. He could have witnessed my display the past week? Now I was so ashamed. Could he have seen my little clitty from across the yards?

After crying again, I considered his note and re-read it. Was I reading something between the lines? 'His new woman'? 'you are or WERE'? I was so unhinged I got a glass of white wine even though it was only 2pm.

I needed the afternoon to think of how to see him. He worked in midtown so at 6pm I walked to his address to await his return on the steps of his Brownstone. This could prove a fool's errand. Now my phone was ringing, a unique sound that meant my office needed me. I returned to my apartment to deal with the office call.

After I dealt with the office matter it looked at the clock, 6:40pm. I saw that Charles had tried to reach me on the cell. The message was simple :

"I need to see you soon."

It was date stamped at 6:28pm. I considered what to do. I decided to run to him, but I had to dress just so. I entered my closet but the impulse to be clean lead to my ablutions and then a quick shower. I just threw on a dress without stockings nor a bra. Just a thong and a dress. I slipped on my flats and ran down the stairs but realized I forgot the pearls. Returning I placed the pearl collar about my neck, touching the very discrete bump at my throat. Maybe it was the tell?

I walked quickly around the block and paused at the bottom of Charles stoop. I had an idea about what I was about to do, but it wasn't a complete plan. I stepped up each of the stairs slowly considering my options. I turned to return home; stop girl. Go to the bell and ring for Charles!

"Hello?" it was his voice but I couldn't speak.

"Is someone there?" I was panicking. He wanted me right?

"Charles it's me, Louisa."

The door buzzed and I pushed it, but I heard the sound of falling feet, pounding on the stair. We met on the second landing and he embraced me, kissing me deeply, my very being. Wow, he did want me. After some moments we walked up to his apartment. I didn't watch the steps, nor the space, I was looking into his face, his eyes, and I felt his semi-hardness again.

He opened the door; I pushed him aside and slammed it shut. Dropping to my knees I pulled open his zipper while looking up to his eyes, reaching within for the rising hardness. And then my mouth engulfed his sex, his meaty thick long cock. It was now in me, my mouth was loving him. My tongue was making him hard, harder; my fingers grasping the thick cock that was pointing at my future. I wanted his seed in me, I looked again to his face, he was watching me, and my eyes were seeing Charles's soul, while I loved his great cock. I suckled him as he started to pulse, the thickness swelling in my mouth and hand. And boom, he exploded into me, my tongue trying to capture all of his essence. I loved his salty seed, as it filled my mouth a bit escape and dribbled down my right cheek. Was I in love? I needed more but I was now surprised by my behavior. I wasn't this kind of girl, but I jumped up, the cum still on my cheek, and kissed him. I nearly collapsed but I had to run away. Turning, I opened the door and ran down the stairs. It took a moment for Charles to realize I was leaving but by then I was on the stairs. He called to me but I needed to get away.

I didn't return home for several hours. I wandered the Upper East Side just trying to comprehend my actions and the possible impact. I was moving slowly along the sidewalk in front of my Brownstone when I saw Charles, sitting near the door.

"I'm just happy to see you're ok Louisa." He arose and started down the steps passing so near. I could feel his warmth and reached to touch him. He took my hand and kissed it gently.

"Call me sometime tomorrow, and get some sleep. I loved your very special kiss Louisa," and he stepped away while looking over his shoulder, smiling.

In the morning I decided to ask him to a late lunch, but I had a lot to do. My hairdresser found a spot for me at 10:30am. I'd planned my outfit, hoping we might find a reason to runoff the afternoon. I texted Charles and he agreed to meet at the MoMA bar at 1:30pm. I had to get my face just right and was dressing at 12:30pm. For this date I was going with the lacy ivory lingerie, a shelf bra and nude hose with a lovely 4" white lace welt, a lovely white suit and 5" white heels. The clincher wasn't necessary but I wanted to be dressed just so he'd want to spend the afternoon with me; just me and Charles. I'd primed my rosebud after my cleansing. Looking into the mirror I placed the pearl collar about my neck; they were so beautiful. Then I brushed out my hair and set it in a half up bun. My afternoon face was easy; mascara and lipstick, oh and some blush. I was in a taxi at 1:10pm and traffic was only a bit heavy. The young cute driver tried to flirt.

"Miss you must be going to a photo shoot. You look so beautiful. And you've got a great smile, and wow, sexy legs." I smiled but turned to watch the pedestrians along the way down Fifth Avenue.

I was seated at the Bar when Charles turned the corner entering the MoMA bar. He smiled when he saw me. I turned on the stool as he approached, my legs flashing my stockings, he kissed me tenderly and grasped my waist.

"You are a vision my beautiful girlfriend. Can you buy me a drink?"

We talked of simple things, but I stopped him.

"Charles, I want to apologize for my behavior yesterday. I can't say I didn't want to have you, but my running away surprised me. You're special to see me today."

"You're kidding, right? You needn't ask for my forgiveness Louisa."

"But do you still want me Charles, even though I acted like a slut, I mean do you want me, like I want you?"

He just tilted his head and moved closer, then he kissed me deeply, the longing evident.

"Can you spare the afternoon? I'd like to take you to the St. Regis for the afternoon."

We left after the glass of white wine. I was happily looking at him as he guided us out to the street to a taxi. Once in the car his hands were all over me; my legs and breasts were clearly ok to him during the short ride. I wasn't too disheveled when I stepped out to the Valet.

We got a simple room, which was still extraordinary. After the Butler left I approached him and pushed his jacket off, turning to hang it up.

"Can I kiss you again?" as I removed my suit jacket.

He smiled as I dropped to my knees and again released his beautiful cock. He wasn't flaccid but I immediately licked his entire length, measuring as I did. He was large but not too big, thick but not too great. My stay-on lipstick was leaving a stain just below his helmet and as he stiffened he stopped me. I needed to be certain he understood. I didn't want to be mistreated nor did I want to deceive him, "Charles do you understand about my, ahh, how I'm not like other girls?"

"Louisa, I need to be inside," he stumbled his speech, "huh, inside your, can I watch you disrobe?" He was nervous as he pulled me to my heels and it was exciting that he needed me to show him what to do.

I smiled and stepped back three steps, turning while I unfastened the button and zip of my skirt. It slipped to the floor and I posed a moment and released the clasp in my hair.

Spinning about on my tall heels I posed my bubble butt by rotating my left hip, "Can I interest you in my unique pussy Big Boy?" Charles leaned back, his bottom on the bed, his cock was hard as I walked closer. He stood and positioned me on the edge of the bed, tittering on my 5" heels. He seemed to be aware of my thong as he pushed it aside and licked me deeply, his tongue at my hole. He placed his cock at my opening.

"You need to take over Louisa. Slide my cock inside your body please." I would handle his meaty cock, reaching for the shaft I settled just the tip into my opening and I paused for a breathe. Turning to look over my shoulder at Charles I slid down a few inches and stopped. I worked my hips in a slow circle, holding him inside me. I continued so slowly, relishing his girth as his balls reached my bum.

"You're so tight and smooth dear. Fuck my cock baby."

Slowly I increased the pace of the plunging, and the depth, but I couldn't easily look to his face. I paused and he slid out of me and I mounted the bed. He followed me lying down, his head on a pillow. I shifted up toward him while on my knees, looking into his eyes I pushed down atop his cock.

"Do you like my pussy just a bit? Can you see fucking me every day honey? I need a lot of cock, and your sweet seed. You're getting a bit flushed Big Boy. Can you please fill my pussy? I want you to erupt inside of me dear. Or do you want to fill my mouth? Please just love me, love my body, love my heart."

He couldn't hold his orgasm any longer, and Charles came strongly, and I came as well. Maybe not a release like a boy but I trembled as I rode his great cock like a pornstar, my heels aside his knees. We made love a second time a bit later, after he inspected my clitty and licked my gushing rosebud. He snowballed his seed with me. The champagne arrived and I covered up when the sweet young waiter came in, his dick semi-erect seeing my scattered lingerie.

We talked until near dinnertime. He explained how he'd come to appreciate the world of transfemmes. Early this year he had dated a girl from a Canadian city for a month while on an assignment. She wasn't totally into guys and therefore not for him. I thanked the good fairy for finding this special man. He seemed to love my body, and just before dinner he took my clitty in his lips and though small, I released a small amount of sweet seed.

I was falling in love with Charles.

On Wednesday morning I had to get home so I left Charles at the Hotel around 6am. Before I left I woke him with my mouth on this beautiful soft cock. He was limp but my mouth settled that quickly. His seed was deep in my belly as I got the taxi; a breakfast before an office day.

Tess called me later that afternoon. "So is he as nice as you'd hope? As sexy as he appeared?"

I gushed for nearly twenty minutes. She got a clear understanding after I said 'I love his cock' four times.

"So he knows of your history?"

Tess could be such a big sis "Of course he does."

"And you told him about Madeline and I?"

"No way dear Tess. That's for you to decide, not me. But don't worry. Charles will love you two beauties."

Later that evening we spoke on the phone, Charles asked if he could visit that evening but I was behind at work. We agreed to sleep at his apartment Thursday night. We discussed getting some take-out, but the sex was what we both intended to enjoy. We awaited the delivery petting and kissing on the couch. As soon as the bill was settled he stripped off my dress and laid me across the sofa arm. Taking me from behind. Previously this hadn't been a favorite for me. Maybe he just was special, his cock slipped deeply inside me, not as deep as my toy had the other day, but his cock was alive and warm and I came more quickly then the first two times. He filled my cunny and I wondered if he might clean me like the other evening.