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Tilted Kilt

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Transsexual meets Mom then introduced to Daughter.
4.6k words
4.64
109.9k
84

Part 1 of the 5 part series

Updated 10/24/2022
Created 02/19/2009
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"Hey Shari. Take a look at the couple in the corner for me. Don't they look like a couple to you?"

Shari took a glance while loading her tray with four cold beers in frosty glasses. "Yeah Danika, I'd guess they are. Why do you ask?"

"Because she slipped me her phone number when he was in the boy's room. She just smiled and said she'd like me to call her soon."

"No Shit?", looking at them a little closer now. "She is quite attractive, though a bit older than your usual dates."

The man and woman in question were both in their mid-40's and well-dressed. "You gonna call her?"

"I don't know. I'll have to think about it some on my day off tomorrow."

#

Shari and I work as waitresses at a sports bar called the "Tilted Kilt". It's a sports bar, but we wear skimpy little red kilts for skirts and white shirts that barely cover our breasts and show lots of skin. White, knee-high socks cap off the outfit and needless to say, we do get lots of ogling and propositions. The tips can be quite good for the girls with bodies and aren't afraid to show their skin. I always make sure I wear a bra that's at least one cup size too small for my 36C breasts. A sexy little tattoo on my lower back that disappears into my kilt gets the customers - men and women - looking at me, coming and going.

Shari is my best friend and my roommate. We share a little two bedroom apartment in the downtown San Diego area that has become quite trendy in the past few years. It's great that we can also walk the four blocks to work since parking can be tough in the area. We're both 24 and have been friends since college. In fact, we dated some in college but realized we were happier just being friends.

Sunday was a chilly, rain-filled day so I slept in and enjoyed the feeling of the warm sheets on my skin. I finally crawled out of bed around noon, knowing I had laundry and some other things I had to get done on my day off. Shari was already at work and so the apartment was quiet. As I sorted through my laundry, I found the slip of paper with Susan's phone number from the night before. The image of the woman went through my mind as I pictured her face. She was quite attractive with shoulder-length auburn hair and expressive eyes. The touch of her hand when she forced the slip of paper with her number into my hand had been electric. Her eyes lit up as she looked into mine when she told me to call her. The thought of the moment now had my nipples becoming sensitive under my long t-shirt. It had been too long since I'd had sex!

Shaking my head, I finished sorting the laundry and pulled on a pair of sweats over my bikinis as I headed to the laundry room. Later in the day, I found myself finishing up the grocery shopping in the neighborhood but my thoughts kept roaming back to Susan's offer. I felt myself becoming aroused and blushed at the thought of someone seeing me.

Monday morning had me thinking about calling Susan. I didn't have to be to work until 4 pm so I had the day to myself. After a hot shower (though a cold one might have been more appropriate), I dialed Susan's number. The phone rang four times before I heard her voice.

"Hello, this is Susan."

"Susan, hi this is Danika," I could hear the pause on her end of the line, "from the Tilted Kilt Saturday night."

"Yes, I remember." She seemed distracted and I wondered if I should have called at all. "I'm going into a meeting now and can't talk. Can I call you at 11?"

"Sure, no problem. I don't work until 4." Susan hung up with a short good-bye. I looked at the clock on the wall and it was just before 10. I had an hour to kill and surprisingly I could feel butterflies in my stomach. Shari had gotten up so I fixed us breakfast and we talked while I waited for her call.

Just after 11 the phone rang. I saw her number and forced myself to let it ring three times before answering. "Hello Susan"

"Hi Danika. I'm sorry I was a bit curt when you called. I had three people in my office. I'm sure you understand."

Breathing a sigh of relief that it wasn't me, "Of course. It's not a problem at all. Is this a better time for you to talk?"

"Yes, I have a few minutes for you. I'm pleased you called me. I wasn't sure you would." When I hesitated in responding, she continued "You are a very beautiful girl. I would love to see you sometime."

"I would like that very much. And thank you."

We talked for a couple more minutes finding a time that worked for us both. I told her I had Thursday night off and she said her husband was out of town. So they were a couple, I thought to myself.

When I hung up, I turned to Shari and said "Let's go shopping. I need something for my night out!" We headed to the mall so I could find something sexy for Susan.

#

I had a lunch shift on Thursday and thought the end would never arrive. It was probably good that I had work to keep me busy, but I was anxious to get home and get ready for the evening. Susan set up the evening, leaving me a voicemail while I was working with the time and place. She did add that she couldn't wait to see me again. Since my waitress outfit leaves little to the imagination, I knew Susan was attracted to my body and wanted to show it off tonight. The outfit Shari and I found at the mall on Monday would do just that. I wore my slightly longer than shoulder-length blonde hair down. I wore my sexiest boyshorts and just an undercup bra. They were both in white lace. I pulled a thin, blue sweater over my head. I could already feel my nipples pressing against the sweater. Next, I pulled an off-white mid-thigh skirt over my hips. Stepping into three-inch heels, they only accented my long legs. I'm 5'7" in my bare feet.

I took a cab the ten blocks to the restaurant. I had heard of it, but had never been there. It was way out of my price range for a meal. It sat atop a hotel, the thirty-fourth floor. I took a private elevator to the restaurant. The hostess greeted me warmly as the doors opened to a private lobby. I gave her my name and told her I was meeting a friend for dinner. "Susan?" she asked with a beautiful smile.

"Yes. Is she here already?" I thought I was early.

"Yes. Please follow me and I'll show you to your table." As I walked through the restaurant, I noticed there were no tables visible. It seemed all the booths were cloaked with a curtain for privacy.

The hostess knocked once then opened the curtain to allow me entrance. The curtain closed behind me. Susan was smiling up at me as her eyes drank in my appearance. She was even more attractive than I had remembered. "Please sit down. I ordered champagne for us." I looked past her shoulder and saw the city skyline out the darkened glass and the Pacific Ocean in the distance. I slid into the booth, sitting next to her as close as I thought appropriate.

We made small talk with interruptions for the waiter to take our order for dinner and to serve us. He was drop-dead gorgeous in his own right. The second bottle of champagne had me quite light-headed by the end of dinner. The waiter was most discreet when took our dessert order, not saying a word as Susan pressed her lips to mine and her hand cupping my breast.

"Do you live alone? Is it near here?"

"I have a roommate," knowing what my next statement would mean. "But she won't be home until after 2. It's a $10 cab ride from here."

Susan's eyes lit up with that information. "Wonderful! How about we have them pack the dessert to go and we can eat at your place?" It wasn't really a question. It was obvious from the beginning that Susan was used to being in control.

We flirted in the back seat of the cab for the quick ride to my apartment. As soon as we walked through the doorway, Susan shut it behind us and pressed me to the door. Her lips were tight to mine, her tongue invading my wanting mouth. I dropped the desserts on the floor as her hands cupped my breasts through the sweater. My nipples were already hard in anticipation of her touch. In a flash, her hands were under my sweater and pulling it over my head. My chest was heaving from breathing hard. Her lips wrapped around my left nipple as she bit down on it causing me to gasp. Susan pressed her left leg between my thighs and applied pressure. Her mouth sucked on my breast, taking my hard nipple in her mouth. My body was on fire from her touch.

Without warning, her left hand moved under my skirt and cupped my crotch. Her mouth left my breast as she felt me for the first time. "What the FUCK is this?" My cock had become quite aroused from her attentions and had become un-tucked. Without letting go, Susan backed up a half step and lifted my skirt with her right hand. I just stood straight against the door. She ripped the boyshorts from my hips and my cock snapped half-erect in front of me.

"Susan ... let me explain please." I could hear the pleading in my voice. I really didn't expect it to get this hot this fast. I thought I'd have a chance to tell her.

She just smiled a very devilish smile, "Does it work?"

It took me a moment to hear what she asked and in that moment, she tugged on it with her left hand. "Yes," was all I could breathlessly say to her.

Not letting go of my cock, Susan pressed her body back against mine. Her mouth crushed my lips with lust as her tongue tussled with mine. She was jerking my cock with her right hand as her left hand squeezed my asscheeks. Letting go of my body, I could feel her fumbling with her skirt before it fell to the floor. Susan was just an inch or so shorter than me, our bodies a sexual match. She only wore a g-string bikini so she merely pulled it to the side of her pussy and with her right hand pressed the head of my cock to her pussy. "Show me how it works!"

My cock is eight inches long and more than and inch and a half in diameter. I was already dripping pre-cum as the tip split open her pussy lips. I reached around and grasped her firm asscheeks shoving my cock deeper into her pussy. We shuffled our feet so I had her back against the door now. I thrust my hips up into her pussy, my cock stretching her wide open as she took all my length. She gasped as she felt my full size for the first time. With the door for support, I could feel her thighs wrapping around my waist as I drove my cock in and out of her ever-wetter pussy. Her body took my cock with gusto. Our lips crushed together in an intense kiss as I felt her body beginning to shake. That was all it took for my cock to blast a long stream of cum into waiting pussy. Her muscles heaved and she let go her own orgasm. Her body shuddered and shook against mine as I slowed the fucking of my cock in her pussy. Slowly, her legs lowered to the floor and I slumped against her. Susan smiled and gave me a kiss on the lips. "Wow! You are quite the surprise ... a very big surprise." I took her hand and led her to my bedroom.

I unfastened my bra and slipped out of my skirt and heels as Susan undressed as well. I took in her body. Yes, she was in her mid-40's but her body was tanned and firm. Her breasts were a bit smaller than mine, perhaps a 34C but with very full nipples. Her pussy was shaved smooth and I could see traces of our cum beginning to run down her inner thighs. And Susan took in my body as well. She shook her head as her eyes examined my nearly erect cock. I pulled back the covers and motioned for her to get on her back. I crawled between her legs and began to lick the combined juices that were running down her thighs. I continued to lick and kiss up her thighs, Susan spreading them wide to accommodate me. My tongue soon found her erect clit. Susan loudly gasped when I pressed my tongue against her clit. My mouth covered the area and my tongue raked back and forth across it's surface. Two fingers teased her pussy lips, slipping in and out of her. My tongue would dip down to take a taste of those juices before returning to her clit. Looking over her belly, I could see her playing with her nipples and sucking on her fingers.

My fingers, coated in our juices, pressed to the rim of her asshole. My tongue raking her clit, I could feel her breathing shorten. After tracing circles around it, I pushed the two fingers inside her asshole. It opened to take them gladly and her body spasmed as her orgasm washed over her body. My fingers slowly fucked her ass as I continued to torment her clit. Susan was crying out as the passion wracked her body. I didn't stop until she found the strength to push me away from her body. I moved up beside Susan's body and cuddled against her. My fingers playing with her nipples as she turned her head to kiss me. Her lips lingered as she tasted her own sex on my lips.

After catching her breath, I felt Susan's hand stroking my cock. When she had me half-erect, Susan crawled down my body and took my cock in her mouth. Her tongue was magical as it danced over my aroused skin. She soon had my entire cock in her warm mouth. She was taking me all the way to the base as she fucked my cock with her mouth. I could feel the back of her throat on my head but she continued to ride my cock. By now, she was lying on my body with my face between her thighs. My mouth was suckling her pussy lips as my fingers played with her asshole. We both knew she had me close to cumming and she abruptly stopped. Before I could say a word, she had scrambled around to be kneeling over my crotch.

"Can you get that monster up my ass?" With that, she spit on her fingers and rubbed them over the rim. Susan then lowered her hips down on my cock. I felt my crown pressing against her slicked, but tight, asshole. I lay still as she worked her body on my cock. I've not been with many that wanted to try and take my cock up their ass but Susan left no doubt. With a slight push, my cock popped inside her rim. Susan let out a guttural groan as my cock opened up her asshole. She was slowly lowering and rising on my cock, taking me inch by inch and enjoying every moment. My hands rested on her hips as she continued to ride up and down my cock, letting her body expand to take my size. She grinned that devilish grin I'd seen earlier when she finally lowered her body onto the full length of my eight inches of erection.

Susan just paused and rested as her body accommodated my large intrusion. She reached forward and pulled on my nipples as she now began to rock her hips up and down my cock. Susan was lifting four to six inches up and down my cock as I fucked her asshole. She was pulling and pinching my already tender nipples and the sensation was pushing me over the edge. "Oh Susan ... ride me ... Ride Me!" I cried out as I felt my cock fill her asshole with cum. She laughed as she felt the warm stream jetting inside her and rode me harder. She was bouncing up and down on my cock as she milked a second stream from me. I was near exhaustion and finally she dropped down on my semi-erect cock and covered my body with hers.

#

Susan and I would get together a couple times a week for the next couple months. Usually she would invite me to dinner as foreplay, but a couple times she stopped by my apartment during the day for a quick fuck before she went back to work. We got along great, though our conversations were pretty casual - not really delving into the others personal lives. One day Susan changed this by mentioning her nineteen year-old daughter. She had been away at college for her freshman year, but had returned a couple nights earlier for spring break. While we were lying side-by-side after fucking, Susan recounted the conversation she'd had with her daughter the previous night. Susan was surprised to learn her daughter had started fooling around with her female roommate and was swearing off guys. Susan didn't object to her being with women, but she thought it was crazy to do so without ever fucking a cock.

Susan had an idea and wondered if I would help her with it. While driving me crazy by softly then roughly handling my cock, she laid out her idea to me. How could I say anything but yes after she took my cock in her warm mouth and sucked me to orgasm?

Two days later, I was standing at the front door of Susan's beach house knocking on the door. A beautiful young woman answered the door. She was a younger version of her mother with longer hair but the same great curves to her body. She was wearing only a bikini that did not hide much to the imagination. "Hi, I'm Danika. You must be Katie."

"I am. Come on in, we're both out on the deck." Susan had invited me over to join her and Katie for fun in the sun. I didn't know what Susan had told Katie our connection, since I was obviously much closer in age to Katie than Susan, but it didn't seem to matter to me. "Can I get you a glass of wine or something else to drink?"

I had the glass of wine in my hand, but nearly dropped it, when Susan walked inside wearing the barest micro-bikini I had ever seen. It really only covered her nipples and the slit between her thighs. She gave me a hug and pressed her body firmly to mine. "Danika, I'm so glad to see you. You met Katie, right?" Katie appeared around the corner with her wine glass refilled. "Let's go outside, the sun is so warm today." Susan pointed to a room where I could drop my purse and change into my suit. The two girls were standing outside when I walked through the sliding door. I left my heels on to accentuate my figure, wearing a light blue bikini. My nipples were already hard from the anticipation of events and seeing their sexy bodies. My bottoms were a bit more conservative than I usually wear, but I didn't want to spoil the surprise!

We spent a couple hours in the sun, drinking wine and making girl talk. At one point, Katie offered to re-apply my suntan lotion and I gladly accepted. Her hands felt so good on my warm, oiled skin. It became obvious that Katie was aware of mine and Susan's relationship but that didn't seem to bother her at all. In fact, it seemed like it sparked her curiosity. When she offered to refill my glass, I gladly accepted. While she was gone, Susan commented that Katie seemed to be turned on by me. I wasn't sure how she knew, but she was right. Katie reappeared with two wine glasses and no bikini. "You don't mind if I get a little more sun, do you?" She smiled as she said it.

My eyes roamed her nineteen year-old firm body. Her breasts were perfectly shaped and hung nicely on her chest. Her belly was flat and firm. And she had just the sexiest patch of dark pubes above her sex. She was delicious to see. "I don't mind at all," I said as I removed my top. Katie handed me the glass of wine then asked if I would apply suntan lotion to her newly uncovered skin. I squeezed the warm lotion onto my hands and applied it to her back and then to her asscheeks. My hands caressed her skin as I pushed the lotion around her skin and down the crack of her bum. I looked over my shoulder and saw Susan's eyes glued to the scene. She appeared mesmerized as my hands, hands that had caressed her body, now caressed the body of her nude daughter.

Katie turned around to face me and her sex was inches from my face. I squirted another glob of lotion into my hands and raised them to her breasts. My hands massaged the lotion on her firm tits as my thumbs lingered on her nipples. I could see her lightly licking her lips as my hands squeezed and caressed her breasts. Trailing over her belly, my hands lowered to her sex. Still covered in lotion, my hands danced around her pussy. I rubbed her hips and worked my way towards the middle ... my fingers now rubbing lotion in her dark pubes and then cupping her pussy. Katie moaned as I touched her and I could feel her body tense at my touch. When I was finished, Katie stood motionless for a moment before bending over and kissing my lightly, but longingly, on the lips.

"Mom, I think you should put lotion on Danika's breasts so they don't burn." It took Susan a moment to realize what was said as she drank in the scene before her.

12


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