Dressed So

My passed relationships weren't as sexually driven as it might seem. I enjoyed my liaisons and affairs but most of the girls who had moved in were in need of very specific care. I insisted on strong penetrative sex and mostly resisted providing them the opposite. Since Lisa had moved out I'd focused on learning to appreciate how to treat a lover's needs as my own. Last month I'd spent the holiday weekend fucking a lesbian I'd met at a party. During the long weekend she had shown me the beauty of penetrative anal sex. Prior to her request to fuck my bum I had only allowed my lovers to lick me there. All of the girls had wanted me to fuck them with a strap-on, and I did sometimes, but I failed to orgasm during these sessions while bringing them off and therefore I didn't offer this unless requested. Never did I consent to having my tight passage entered. The weekend with Mary I had reached orgasm as I fucked her butt but I had multiple orgasms when she deeply loved my ass. This was a new adventure and required careful cleansing. I had decided to work at it and tried with my toys with success and learned the technique. Patience was important. If I had further explored this act with Lisa or possibly Jenna, the brunette beauty I'd lived with for 15 months over two years ago, I might be a married woman now.

I was at the doctor when I received a cell call from an unknown number. "This is Tess, can you meet me for a drink this evening?" Tonight I was busy with a client and couldn't meet, but agreed to do so the following evening. This began a slow seduction, but not by me; Tess was after me.

Our drink turned into dinner, but I passed off her flirting. "We'll see each other soon enough dear" but she kept at me. Flowers arrived at the office the next morning, and the next afternoon there was a box delivered. Inside were a lingerie outfit, quite beautiful, and a note with a Poem.

She said please she said she feels

a young woman

like one with desire

For a union

but must flirt

to tease and warm

with fingers

an other members to compare

The Poem was just the beginning for she left a phone message, then a sextext of her bum. Clearly we had to get together. I responded to only the sextext, with a smile and an address; she had to pick me up.

I was trying to take this slow, to focus on the details I'd previously missed in my relationships, so I agreed only to meet for drinks and dinner. She'd found a lovely place with a mixed crowd, so we weren't the only 'gay' couple. I was dressed to attract her eye and imagination. I selected the pale white lingerie she sent me including a very delicate waist suspender. These were fine garments and I wanted to play the part of a submissive lesbian. My legs were in sheer nylon hose with nude colored 120mm heels. She knew what I had on beneath the ivory skirt and white sheer blouse with a scoop neck but I worn a chemise to subtly conceal my body and the soft lingerie.

"You're taunting me, but your manner of flirting is very discreet. I'd like to take you to bed this night, to slowly remove those garments and play over your body with my tongue, then slip inside you." She was trembling with excitement yet I played mute, awaiting rather than giving her any sign. Beneath the table she slipped her right heel off and stroked my legs with her hose covered foot, but I simply sipped the wine and commented on the vintage.

"When I allow you to my home you can bring this along, it's a great Pinot, I'd love that Tess." Then I was silent as she continued to speak of her attraction, the massage beneath the table dressing continued. I changed the path of the discussion, asking her to tell me of her first encounter. The story went on nearly an hour. Not about a boy and her but of an older woman from her neighborhood named Cathy. The woman was divorced but with a child who Tess help care for. Cathy was instrumental when Tess was still living as a boy, finding and buying her the hormones that started the changes Tess desired. She also helped train Tess about beauty care and makeup. Tess had worn her hair quite long but it was a mess and Cathy brought her to a salon that helped repair and shape her hair while still easily converted with a band to a boy's style.

Their relationship became sexual when Cathy deemed Tess could pass and only if they were both properly dressed, lingerie as well as dresses. Their loving didn't include any penetration for over 24 months. Tess finally convinced Cathy to use a strap-on in bed one afternoon. Tess was more than ready for the love making and Cathy had enjoyed the sex as well. The next day Cathy had acted strange when Tess came by. Though Cathy didn't mention the interlude Tess sensed that something was different.

Tess said "Soon after that Cathy stopped calling for me to help with the sitting and within a month she made it clear our relationship had been spoiled by the act of penetrating my bottom." I saw her eyes moisten but no tears fell. "Anyway I was off to Chicago very soon after and classes distracted my memories. Why I can still feel this pain I don't know. Cathy was of course a beautiful and a tender lover. I clearly needed more though and the split was therefore a good thing."

I sat quietly listening and she suggested we head to her apartment. "Tess I want you as well, but I want us to settle a good foundation without sex, if that's alright with you. I feel it will be for the best dear." I reached across the table for her right hand, a diamond on the fourth digit. "That a beautiful stone, a gift?"

"I had a serious male admirer for nearly a year, his true gift was his great cock but he tried to marry me as well. I just knew it wouldn't work. I wanted his sister more than him," she laughed.

So we shared a cab home, she watching me enter the building, than the cab moved back into traffic. Again the next morning flowers arrived, and another box and a poem, this time the gift was a realdoe insertable! I smiled knowing I would use it with Tess soon. "Stop sending me these toys to my office Tess. The distraction isn't helping me do my work!" She asked me for another date, Friday evening, at a surprise location. Reluctantly I agreed, so long as she didn't assume we'd be in bed that night. She chuckled "I promise not Friday."

I decided that evening to research the difficulty transfemmes encounter in the job market and business. Tess had an advanced degree in computer software and worked in the IT department of a small international firm. That appeared to be one of the few great jobs and the firm was on the record as supportive of the LGBT community. Her sole art venture was due to meeting several artists at the end of her college studies. Two of these had become big and Tess enjoyed the fruits of their success. She would eventually find out about all of my passed lovers, as well as my financial background. We could be every good for each other, so long as I didn't mess it up. I thought of Jenna, how I loved her breasts (the best boob job any woman could get), and she had a great cock too. I'd allowed her to simply leave and now I thought to call.

"I know you asked me not to call, but I just had to find out if you're ok?" She didn't speak for a moment "I'm with someone right now, but he's in the bath. Email or a text is more discreet girl, you know that." She paused "But I'm just fine, no long term relationship but I'm ok with that. I'm staying healthy and sane, and you?" I shared the recent past and we agreed to speak in a couple of months. It was clear she was sleeping around, I guy? She'd not been with a guy in years as far as I knew.

Friday evening Tess arrived by cab and had told the driver to wait, she came into the Lobby and asked for me. Via the phone I said "You're 20 minutes early! But it's fine Tess, I'll be ready in a few minutes. Come upstairs while I finish."

She entered the unlocked apartment a minute later and I called for her to sit and enjoy a glass of Chardonnay I set for her. I entered the Living Room ten minutes later ready to leave to find her looking over my photos and Library collection. "This one of you is beautiful, but who's the girl?" Her question distracted my attention of her flouncy tiered, cream colored dress.

I move to her side, in my heels she was just a bit shorter, "That one is Jenna, but let's not go there right now." She turned quickly and kissed me, her tongue finding mine and playing. I noted how quickly moist my pussy became as she felt my breasts. "Slow down honey." I said pausing but not ending the kiss. "I love you in this color" I whispered in her ear.

Tess said, "We've got a few minutes" her hand running down my back, and started to lift my hem.

"No we don't young Lady! Let's go before there's an accident, my panties are just a bit wet and not soaked yet."

In the elevator she drew me to her and I felt our breasts touching, hers just a bit larger, the nipples erect and noticeable through the fabrics of her spring outfit. "Tess, please stop for now I am quite moist. That's what you were trying for, so yes my pussy wants you. The toy you sent me hasn't left my mind. It's quite stout you know." She smiled and took my hand and caressed along the front of her beautiful dress. "You tuck very well, or your clitty is quite small Tess." she smacked my hand and kissed me roughly.

"You can't wait to see my clit can you? You've been lusting after me, huh? Well I'm a bit more stout but also very soft, and very attracted to you, and can't wait to fuck you!" Her hand reached the welt of my stocking. "You had better always dress just so for me dear. I will for you too." We kissed just as the doors opened and my middle-aged neighbor Ms. Lester looked up and frowned. She of course knew of my girlfriends, but she didn't like the public display she'd just witnessed.

Dinner was great, the wine perfect and we didn't finish until nearly 10:30pm. Leaving the restaurant, our heels clicking on the bluestone slabs I asked "Shall we have a night cap at the Bar down the street?" Tess looked pensive.

"I'm not going to sleep with you this night, I told you earlier this week we need to go slowly Tess. I think you're too special to lose and want our first time to be just perfect."

She turned upon her heels, a beautiful and tall pair strapped about her lower leg well above the ankle. "Ok, then let's stop but at a wine bar nearby instead." They had a wonderful cellar and Tess clearly knew what to order. The Gamay arrived and was perfect. I failed to read the label until a bit later, Point-G 2006. The sly smile on her face made me realize Tess had a plan, and I was the target. We were seated in a little sofa wrapped about a café table. I had slipped off my heels and slid my feet to the edge while Tess massaged my hose covered legs. She spoke softly, cooing her words. As midnight approached I softly asked Tess to get me a cab home.

"Won't you let me bring you to my home?" We were reclining on a sofa and I moved to look down at her.

"You started this evening making my panties wet Tess, and I assure you I want to return with you, but I was very clear." I stood and slipped on my heels, turning to leave. She jumped up and tried to hold me, "NO Tess, not this night, soon yes, but not tonight." I continued to the door, she slightly behind trying to get her own shoes. As I reached the door a cab was just pulling up and I had my wrap and signaled to the doorman.

"When can I see you again?" she pleaded.

"We'll speak early next week Tess" I turned and gave her a quick kiss, then entered the open door of the cab. I was upset and also aware I was being a bit of a tease.

I was so hot for Tess but I had settled my path. The relationship was more important than the sex, at least right now. I thought of our evening, of her touch and the kisses. I hadn't checked my messages in more than 36 hours and on the ride home found that Jenna had tried to reach me. The message said:

"Call ANY time".

I paused to consider the possible benefits of pursuing Tess while re-visiting with Jenna. It could be interesting to better understand what I had lost over ten month ago; I quickly placed the call even though it was after 12. Jenna picked up on the second ring.

"I'm glad you've call. Where are you?" she asked. "Please come see me right this moment, please?" I considered how aroused Tess had made me and re-directed the cab to Jenna's new address.

I arrived and was buzzed passed the entry; she was waiting for me. The mirrored metal elevator door allowed me to collect myself, straighten my outfit and run a brush through my hair. Jenna met the elevator and jumped to kiss me, "Come to me you sexy Lady". We entered her apartment hand in hand and she led me to the sofa near the windows. We hadn't seen each other in so long yet she knew what she wanted and I think she understood from my questions last week where to take me.

"I still love you, and miss you, but can you be with me?" She paused in her excitement to settle into a reclined position that allowed her gown to fall open. Her lovely breasts were just held by the thin material, which fell to her open thighs, just covering the tip of her semi hard clit. I considered her beauty and shifted closer. She'd clearly showered and re-done her face.

"Yes Jenna, I need you tonight as well, but I've changed in important ways since we last were together." She smiled knowingly. Previously our lovemaking would include kissing, petting and lead to her entering me after I played with her clit. I would occasionally penetrate her. She simply looked over to the side table. I followed her eyes and saw the fleshy strap-on, proud and erect.

"Is that what you mean by 'changed' sexy Lady?" She moved and kissed me, while reaching for my skirt zip. "Is that the way we'll play tonight?" The phallus was extraordinarily large.

She started to un-button my blouse. "Can you handle fucking me, humm?" She caressed my breasts while releasing the bra. I felt so alive and my pussy was so wet. Her hand came to my mound. "Why are your panties so wet sexy Lady? Missing me a little, or has someone else got you humming?" I was quiet, allowing her to slip off the damp thong and remove my chemise and bra, as she reached for the strap-on with her other hand.

"Let me settle this for you." The harness was a flesh colored material and concealed a small protrusion. "Don't worry, we're both going to come tonight, maybe at the same moment humm?"

I considered what I wanted to do, to fuck her like she enjoyed, allowing her to do my ass as well? She had wanted my tight opening for so long. My right hand reached for the large phallus, as Jenna cinched the strap tight and my mound felt the subtle vibration begin. "Turn to me sexy Lady, I want to see your cock." I held the phallus and nodded to Jenna. She moved close and dropped to allow my phallus to enter her mouth. Moaning softly I watched as she ran her tongue along the length, across the tip and deep into her throat.

She removed the phallus slowly "I've been sucking a bit more real cock as of late, but not enough pussy. Can you fuck my mouth please?" I trained my attention on the willing soft mouth and slowly began to move into her, while holding her shoulder.

"Watch the teeth Jenna, and hold my balls gently. Kiss the tip girl, yes, run your tongue around the smooth head Jenna. I'll let you in on a secret, I've missed your beautiful tits and your great clit too." I pushed her to lay back and this exposed her tight opening. Her thong now concealed her stiffness so I pushed the panel away from her pink rosebud. I ran the moistened cock up and down her perineum, teasing her while my fingers entered her mouth. "Suck on these while we get you lubed."

"I won't need any dear, I'm so ready for your cock, please enter me," So I slowly centered the stiffness and pressed up and into her, pausing with just the large helmet inside. "That sooo good sexy Lady, yes go slow, I want to feel each centimeter enter my body dear. Ooh that's just perfect, now all the way in please, oohh yes, all of your cock sexy Lady, press your nuts into my butt!" I leaned forward to kiss Jenna, holding her chin with my right hand, at the same moment I withdrew the phallus some 5cm, then slid back in deeply.

"Oh Lady that's what I need, I need your cock, fuck me now, yes, Sexy, fuck me!" I started at a pace, fucking her but deeply and kept my face close to hers and kissing her, her mouth, her cheek, her ears, while caressing her breast with my free hand. We were looking into each other's eyes,

"You still love me, after I hurt you?" I said.

"Sexy Lady you're inside me and my peak is near, yes I do, I do love you, I love your cock inside me. I only wish it could shoot me full of your seed. Keep fucking me!" she closed her eyes. I had notice the stir within my pussy, though not penetrated, the vibration began to cause my pussy to contract, and I was going to come with Jenna. We had never experienced a mutual orgasm like this before. I increased the pace and the stimulation at my mound moved just to the right and I started to peak, and she was gripping my body, holding me close as the deep fucking brought her own release. She loudly orgasmed as the phallus pounded her tight bottom.

Afterward we lay relaxing in each other's arms in the bedroom, with a cool white wine. "Will you let me fuck both of your openings this night Lady?"

I turned to look at her face, "don't be greedy Jenna, but yes, near morning we'll make love again ok? Why the urgent call tonight? Were you alone or just horny?"

She started a story about her passed month, with first a man, then a woman, confusion on her part, but some great sex. The woman wanted her to move in with her and her husband, but Jenna worried it might get too kinky. She just needed some time with a friend. My call last week had opened the door, so she'd reach for me. I was happy she had called, for the release was what I needed.

"So you decided to find out how sexy your butt is Lady? I've always loved your little hole. Now you'll let me in, humm?"

I decided to be as truthful as possible. "I met someone who insisted I allow her in, over 36 hours she fucked me repeatedly and I came so strongly Jenna. I realize you tried to get me comfortable with anal for so long. I resisted foolishly I now see."

Jenna smiled wickedly "Turn over I want to kiss your ass Lady," she rolled me a bit onto my side and dove beneath the covers, licking me with intent, then slipped her middle finger into me. "You are accessible Lady!" She played there, licking, stroking and rimming me for ten minutes.

Jenna was calm as she lifted my bum and positioned a pillow. She stroked my back, and ran her hands under to grasp my breasts, thumbing my nipples gently. She moistened my cleft with a lube and then played her clit along my slit and then my anus. Without a word she pressed the tip of her cock inside. I was caught surprised, it was so thick. But the penetration wasn't uncomfortable. She subtly eased a bit in, then a bit more and stopped. She again grasped my tits, "You are ready Lady. Never before have you allowed me inside your bum. Can you sense my excitement? My clit wants to come inside Lady, may we enjoy this first and special loving."

Though fully penetrated, for she had her testes removed years ago, her clit was so beautiful to look at but now I saw it as something to enjoy in a new way. "Oh Jenna, make love to my ass please, slowly, but do fuck me please Jenna." I reached around and used my right hand to hold her close to my back. "Pooch, you're so deep within me Lover. Stay with me Jenna, stay, fuck me, fuck oohhh " I came again but she didn't pause, just continued to fuck me. She moved off my back and we coupled in a reverse cowgirl and fucked until her peak. I'd never felt a seed eruption quite like this inside my bum. We stayed close and quiet until she slipped out, but she quickly moved to enjoy her seed seeping from my opening. Her tongue soothed my rear until she felt she had retrieved most of the juice. Her lips met mine and she pushed the seed into my mouth.