Dressed So Ch. 05: Tess' Friend

I didn't need my lover to enjoy sharing his seed every time. I just loved that he was that much in lust with me. Maybe lust is ok at this point? We fucked in the middle of the night with me riding him reverse cowgirl. My little clitty was bouncing a bit because we were sleeping naked. The size of his phallus was not evident but I felt him deeper in this position. He came holding me tightly and I awoke with his still swollen member in my ass.

In the morning he asked about my past girlfriends.

"How did you know I've been with women?"

He got a bit tense "I just figured you'd have been helped, I mean, in a positive way, ahh, by other women. Women who wanted to enjoy your sexy body." But I wondered if he was being completely forthright.

"Do you feel comfortable that I've had multiple partners Charles?" I hoped he'd say yes.

"Of course, it's just that I've watch others struggle with gender based discrimination. Ahh, someone very close."

I looked at Charles, my big stud, and he had a small tear forming. "Are you ok sweetie? Can you talk about this comfortably?"

I was near enough for a hug and he started to weep "My sister is gay Louisa, and she has struggled to find acceptance. There are so many subtle sub groups in the gay community and Missy hasn't found someone."

This discussion needed more time, I hugged him, "Can we talk about this over the weekend Charles? This is important for me to understand and support you but I've got an appointment in thirty-five minutes, Ok?"

On Friday afternoon I asked Charles to find something to do that evening. I wanted to see Tess and her new lover without being distracted by his nearby phallus. I met the girls in the Bar of the Hotel, and they were dressed for the evening whereas I was in my business skirt and 3" heels.

"Tess didn't tell me you worked in Fashion Louisa. You are so much more beautiful than her old photos" Madeline said as she kissed my cheek and hugged me. "And so slim too."

Her smile made me think of how far I had come to be me. I sat between the two girls and the wine arrived. "So Madeline, how did she snag you? She can get very possessive huh?"

Seeing these two beauties, with their lovely long legs and sexy heels, they're hair styled and the faces made to perfection was great. I didn't miss my lesbian days but women can be so soft and smelled luscious and their skin so smooth. I felt a bit dowdy surrounded by the Manhattan evening crowd.

Tess jumped in "don't be opening any secrets, either of you, at least not until tomorrow. I found her wandering about at my club, you recall I mentioned Faunesse Lulu." Tess and Madeline describe their history.

"Than you've only been together about 3 months?" I sipped the cool wine.

Madeline smiled "It's been nearly four now."

"Has she tied you up yet?" I giggled recalling a past tradition of Tess'.

"I asked for no secrets Lu! And no, I'm into Maddie's beauty, not pain." Tess wasn't perturbed.

We dined at Sette on the East side, than returned to their Hotel for a drink in their room. I could enjoy Tess from a different perspective. I wasn't being chased and pushed by her. Madeline was an amazing beauty, a bit taller than me, and five pound lighter. I found myself strategizing a new diet. Tess looked extraordinary also. She'd trimmed a bit and was happy to be in love. I didn't feel nor look sexy but Tess was shocked by my figure, the length of my hair and the style. She also commented on my manner.

"You've learned a great deal young Lady." Tess ordered a bottle of Moet and met us at the window. "Lets take a bathe, did Maddie show you the crazy tub, with a view?" we entered the Bathe and it was an extraordinary layout.

She ran the water, making the decision for us all.

"Just don't muss my hair, I have to head home before midnight."

So now undressed we slipped slowly into the warm bath as Tess dimmed the lights allowing the City to enter the space. I felt so comfortable with my naked body, but Tess teased me by grabbing my small clitty.

"She wasn't this small 2 years ago!"

"Stop it Tess" said Madeline. "or I'll restrict your access to my bum for two weeks."

That seems to have affected Tess, for she actually blushed and kissed me lightly as an apology.

I wasn't envious of Madeline's pussy but I did move closer and touched her there. "I'm as much a girl as I want to be Tess. Be careful or I may pull Madeline away from you." My hand stayed for only a moment to brush the small trimmed mound.

Madeline turned to kiss me and reached to my clitty. "Do you still get erect at all Louisa?" I stood so she could see my beautiful little clitty. It was barely 2" long at having been in the tub for 10 minutes.

"Oh yes it swells, and though my testes are gone I can still produce a bit of cum. Charles's tongue has brought me off at least once this week."

Tess smiled and moved in closer, touching my clitty. "It's cute and small, but your breasts, they're so perfect. Are you happy with them?"

"Oh God yes, though a bit smaller would have been better. My mother was pretty large so the doctor wasn't surprised. Do you like my areolas?" They are surprisingly large and the nipples stout.

Tess kissed and nibbled the left nipple "Their what I was referring to Sweetie."

We finished the champagne and I stood "I've got an early appointment at the Salon. I can't let Charles see me next to you two without some fast work!"

I dried and dressed quickly and returned to say goodbye while they remained in the warm tub. I was home shortly and asleep within minutes.

In the morning I walked to my appointment and an hour later my pedicure and hair were beautiful. I love walking in flats, a tight pair of jeans and a sweater. Near my corner a guy walking a small dog and wearing a ring spoke to me.

"Can I just say you look lovely, without you're being upset? I'm married but, wow, I needed a vision today!"

I smiled and continued down the street. I had to dress for Tess was taking me shopping and I had less than an hour. My outfit was simple, a pencil skirt, a blouse and heels. Pantyhose were the best for running in and out of dressing rooms. I met Tess outside Bergdoff's and we shopped for two and a half hours.

"Now you have an appropriate dress for tonight Lulu. I can't wait to see you in those wicked sexy heels!"

She'd spent near five thousand dollars adding to my wardrobe; the new heels were over $1,750 alone! My salary didn't allow this level of spending and she knew it. Her generous gifts would be seen this evening. Except the la Perle lingerie, well maybe Charles would get a peek.

Tess asked about my beau, "he's a bit bigger down there than I could have hoped for, but he sure touches all of the right spots with that tool."

"And he's truly ok with your having a bitty clitty?" she smirked as she made her joke.

I pushed her shoulder a bit and smiled. "I think he may be in love already Tess." I then told her of the incident at the top of the stairs.

"And you don't see that as a bit slutty?" We shared other details of our new worlds. She told me about Madeline's ex-girlfriend Jenna. "She's still around, and though I don't feel Maddie loves her I'm not letting down my guard. It may be that she just likes and extra fun of sex with a third, but Jenna's got a smaller clit, not as small as you though. Have the hormones stabilized now?"

Tess's friend was more interesting than I'd first thought. Maybe they were a great match. Tess could get bored if not entertained. At the Hotel we parted and Tess said "I'm going to play with Madeline. See you later dear."

"Your friend is quite a beauty Tess. I've not seen a transition, other then yours and maybe Jenna's as extraordinary. Her little cock is not for us though" she hugged Tess after she put down her bags.

"She's come a long way in two years honey, but her maturity is what I'm most happy about." Tess pushed aside Madeline's dressing gown.

"Can you fuck me, please Mistress?" Tess allowed this role reversal and Maddie knew how to proceed.

"You'd better have completed your ablutions little girl! I'll go and settle the other details. But I want you dressed, is that clear?"

Tess knew what to expect and she ran to her drawers and found a white and pink lingerie set; the hose were stripped and she worked to get them correctly arranged.

Ten minutes later Madeline entered the bedroom wear her heels and a pair of dark pantyhose. She moved to the bed where Tess lay, her bottom up and presented on the four pillows. Madeline saw the subtle glistening of Tess's lube and took her place. She inserted her realdoe slowly, holding the end and teasing Tess.

"Does my girl want my cock in here or in her mouth?"

"Mistress, please don't tease me today, just fuck me, fuck me now please!"

The action was swift as Madeline entered deeply causing Tess to gasped in delight.

"My cock is inside my girl, let me slowly bring you to climax, Tess. Ahh, this cock is, aahh, is pushing me over,"

"Mistress is going to come inside her girl, fuck me deep Maddie." Tess looked over her shoulder as the Madeline withdrew the cock.

"Yes, yes, Mistress is happiest when she's fucking me! Push inside me now please."

"I'm definitely enjoying playing with you Tess, but I'm going to come too soon, maybe, oohhh, damn," she screamed as she peaked still thrusting into Tess's butt.

"Oh Mistress I'll come soon enough. Don't think I've abandoned my orgasm for yours."

The End of Part Five