Daydreaming on Deck

He held me a little tighter, I then moved down and put my head on his chest, when I was in France and California I wore a wig, I was glad that I now had my own hair. I felt much more real like this. I was looking at my long nails on his arm, my nylon leg draped over his. He started to caress me. He put his hand under my chin and we kissed again, it was wonderful. It was exactly what I needed. It was exactly what this bored, depressed, lonely 'woman' needed. His one hand went to my breast as the other held me close. I lightly touched his face with my nails, I played with his messy hair. And we just kissed a sloppy kiss, on his chin on his cheek on his lips. Kissing a man was so different, better somehow and it was unplanned, I was getting a little too turned on. I glanced at his crotch, a man hasn't been attracted to me in so long. Very rarely do I even come in contact with one, just to talk, touch, flirt.

He took my hand and placed it on the front of his pants, and I started to rub. He rubbed my breasts and kissed my neck. I made the most girlish sigh when I got the chills running right down my back, my arms filled with goosebumps, my panties were getting tighter. I wanted him. I wanted him to be happy with my femme appearance. I wanted him to be happy he met a new woman.

I broke away from his embrace, I reached down to his zipper. I heard the teeth rattle, I heard my bracelets jingle. I giggled when I put my hand on his briefs. I made him stand up. I pulled down his pants and shorts, his cock was inches in front of me. I started to rub it, his hands started playing with my hair. I kissed his cock lightly, "I like when a man plays with my hair." My hair and his cock rubbed against my face. I stood up and I felt him take in my scent, I kissed his neck.

"You feel so good against me," He whispered.

His cock was getting bigger, harder, he was very impressive. My hands looked so tiny and feminine jerking him off. He had gotten so quiet, we kissed again as I rubbed his dick. I was watching my grip, my long fingers around him, feeling him. Soon he started breathing more irregularly, moaning lightly, I started pumping a little faster. I then played with his balls, pushing his cock with my wrist. I rubbed his hardness against his body, I used to be good at this. I used to be able to take care of a man. I imagined someone was watching from outside the window, just someone passing by, being pleasantly surprised. I would tell them they could get in line, they could be next.

Logan woke me up out of another daydream. "I'm, I'm gonna cum." he announced, I giggled, I'm making a man orgasm. I pushed harder, I then grabbed the top of his cock and caught his sperm in my fingers, it made it easier to maneuver his dick, play with him, which made it easier to rub. I kept on pushing his cum around his manhood, he leaned back and we kissed again harder. I felt his tongue in my mouth, my hair on his face. He was so much bigger than me, taller, I had to inch up. I opened my eyes wide, I started to cum myself, my 'clit' had reached over my panties, had broken out of its tuck. I rubbed on his hip as I still played with his now softening wet cock. I didn't stop looking at him as I moaned into his lips, lightly kissing them until my orgasm subsided. I gave him one more lick of his lips and chin and laid my head down on his chest. He held me tight. I was worn out, a man had made me happy for the first time in years. If someone looked in the front window at us they would think we were husband and wife.

"I looked up at him. "Can I stay and wake up with you in the morning?"

He glowed, he kissed me. My phone rang.

***

We were a couple of houses away. I could see Linda's car in the driveway.

I wanted to stay with him, I wanted to take more pictures, I was feeling so feminine, it was the type of experience I have been craving. I would come up with something later to tell my wife.

"Can I kiss you goodnight?" He whispered.

I took off my seatbelt I leaned over and he kissed me. A car drove around us, we were taking too long. The driver would tell someone he had seen two teens making out in their car, in the middle of the road. Logan pulled on my hair. We looked at each other. He then ran his fingers through it, making eye contact. He put both hands in my hair, then started to caress my cheeks, my strands in his fingers. He then grabbed another handful of hair from the back of my head and drew me to him again, holding me against his lips. We kissed. I was getting excited all over again. He then let me go, we pulled apart slowly.

"I love your hair and your lips. I want to see both on a pillow on my bed one morning. Hopefully soon."

"Soon." I echoed, I was getting enraptured again but I had to get back to Linda. I had to come up with an excuse anyway, just in case she asked.

We pulled up to the house, I wanted to kiss him again but I had to get out, "Goodnight, and thank you." and slowly made my way to the door. I waved to him and he drove away. I had too much fun tonight, I felt like I didn't deserve it.

***

"Wow, that was a long dinner." Linda got up off the couch, she was ready for bed. "I saw Helene, she told me she saw Logan with a beautiful blonde at that restaurant."

"Did you tell her it was me?"

"Tell her, that my blonde husband was out with a male neighbor, yeah that's what I need spread around our little town."

I shrugged, I didn't care. Years ago she wouldn't tell anyone I was learning and working in France, as a woman. She wouldn't tell anyone I was in Monterey wearing designer dresses, quietly meeting clients for lunch, visiting so many wineries. A woman who was making twice as much money as she was. Now she had her chance, it was her idea, maybe she didn't truly believe it, but she still wouldn't tell anyone her husband was transgender.

***

The next couple of days I dressed up to meet Logan. It was like years ago when I was sneaking around. No one knew how extensive my wardrobe was back then, now it was complete, it was perfect. My body was thin and round and thick in all the right places, I wanted to show off. Last year I promised Linda I would stay on the deck, only a couple of times a week, I wouldn't get too used to it. I wouldn't get too comfortable in my heels or using my long nails. I would just stay in the back, hidden by trees, from people. Things now had to change, I didn't want to be lonely anymore. I had experienced too much, with the women at the salon and the mall, with Logan and Merch. Even with my own progress.

I would see the two of them through the trees, my knees would get weak, my breathing all ragged. They were always surprised by my outfit of the day. I wanted to be a fairy tale, I wanted to be overly feminine and have some fun. I wanted them to see me being a fantasy. Monday I wore a long pale blue ball gown. Long silver earrings, my hair slightly up in the back. I clicked around the wooden deck in my clear plastic heels, taking videos and calling Linda, making sure she wasn't going to be home early. I had already worked, cleaned the house, made dinner, I was ready. I waved when they came in view. I struck a pose when the dog rambled up the steps. I curtseyed and held my chiffon when they got closer.

Logan didn't make fun of me or laugh, he just smiled, dropped the dog's leash, and took me in his arms. We kissed, the trees our only audience. The dog sitting on the bench chewing his birthday bone.

"You look fantastic." He told me, he kissed my neck and slipped his lips down to my breasts. I was thinking were we moving too fast, what was the protocol? I wasn't used to a man's hands on my body.

"So do you." I had my long nails in his hair pushing his face against me. I felt his body against me. "One day can I walk with you and Merch? Can you introduce me to people?"

He looked down at me, he was so tall, he had a sneaky smile on his face. "I can, and I will." His face once again made it down to my breasts, to my stomach, my dress was so full, it had a long slip underneath. The hem came to the ground, even hiding my heels. Logan was squatting his lips millimeters from my 'pussy,' millimeters from the white silk panties hiding it. "Mmm," He said as he nuzzled me, my flat mound, smelling like powder. He looked up at me, holding my hips. "Can I see your legs?"

I smiled, I glowed, no one had ever asked me that before. "Of course, you can." I slowly drew my long dress up, bunching it in my hands, holding it against my body. My ankles, calves, knees, white thighs are now in view.

"Mmm," He kissed my thigh, played with my legs, nuzzled his face against me. He kissed the female mound in my panties, he licked the line of hair hiding in the transparent panties, he sniffed the part of my body right above them, he made me moan. I was shaking as he stood up, I dropped the dress, he sat on a big wooden chair, I fell into his lap. "I wasn't expecting a princess, but now I will always expect the unexpected" He laughed as we kissed, I felt his cock getting hard, felt his body hold me, I was enveloped by his arms. I rotated my ass, feeling his cock swell.

We talked about our date, the restaurant, the cheese plate, and the wine cellar. I told him the music there was perfect, subtle, and romantic. He told me the silverware was ornate and heavy, he told me my eyes looked radiant, my voice soft, subtle, and romantic.

I slipped off him, I got down on my knees. My hands on his thighs. The dog barked, I lost my breath, my heart stopped.

"Good morning."

"Beautiful day out." He told them.

"It is, have a nice day."

I was on my knees leaning against his legs watching the couple holding hands, heading toward the lake. I was glowing. I made him bend down and kiss me. "That was nice. I bet they would have stayed if, well you know." I told him, "I usually never see anyone back there, maybe we can have friends together."

"Maybe? You mean definitely."

I took his cock out, I smelled the musk of his body, I rolled him around my face, my red-painted lips. I put him into my mouth, he slid down so easy. I felt him reach the back of my throat, his hands in my hair again. His hands making me a mess. I moved up and started licking him from the head of his dick to his balls, I kissed him from top to bottom, I licked his hard belly, his hard thighs, his extra hard manhood.

I grabbed his cock with both my hands, loving how he looked gripped with my long red nails. My thick silver bracelets around my wrist, my princess dress enfolding me, making me warm and more excited. "I want you to cum in my mouth." I kissed his cock, I smiled, I licked the head. I licked and licked, then I started pumping, I jerked him off. My tongue right against him, just waiting for him to squirt, shoot, enter me. I rubbed my nylon legs together, feeling the friction, felt myself move in my panties, once again I was getting ready to cum in my panties, two days in a row. I haven't had a man for over five years and now I was on a roll. Now a cock was near my mouth. When was it going to enter my pussy, when was I finally going to lose my virginity?

I started to suck again, I felt myself getting more excited. His hands went into my hair, guiding me on his dick. I was thinking that I wanted to take Logan to visit friends, visit the women in the mall, the salon, have him watch me get my lips done, my hair styled. Even my legs waxed. I wanted him to help me zip up my dresses, take off my corset, hold on to his shoulder so I could slip on my heels. He started to cum, I was daydreaming again. I had a man in my mouth and once again I was drifting off.

"Sabrina, this feels incredible." He was loving this, this would be the best part of his day, his week, his...

"Uhh, " I started to moan, I couldn't breathe again, I was cumming in my panties. How crazy was this, I didn't even have to touch myself, didn't have to push and rub and squeeze. I just had to be near a man, a man I was starting to enjoy, both his company and body.

I cleaned his cock with my tongue, I felt the cum drip down my legs, making my off-white pantyhose slightly sticky. I felt his cum drip down my throat making me more excited, more happy. I tucked him back into his pants in case we were visited by the couple again. I stood in front of him and lifted the dress, exposing my legs, my wet silk panties, I straddled him. My long cotton bodice and sparkly seafoam tulle hovered around his body. We kissed and then I relaxed against him, we would have to do this again. And again.

***

Linda was home, I was all de-glammed. I served her dinner, I thanked her for fixing my closet mirror. Again.

The next day I wore a burgundy Lolita dress. I bought it last Christmas but never wore it, I felt silly, but it looked incredibly sexy on me. Obviously, Logan thought so too, he was hard before he even made it up to the deck. I had him in my mouth and made him cum before we even said hello, before even petting the dog. He didn't want to leave me, looking so young and innocent. We walked the dog together for the first time, but I had to kiss him goodbye, I had to get dinner and drinks ready again for Linda.

After he left I changed into non-gender-specific clothing. I put a meal together. When Linda walked into the kitchen to greet me she asked why I smelled of perfume if Tuesdays weren't one of my regular dressing up days. I just shrugged. "I don't know. I was in the mood to smell nice." I could tell it wasn't a good enough answer. I felt her studying me the entire night. I heard her listening to me talk to myself by my bedroom door.

***

Wednesday morning, Linda wouldn't leave, she was on the phone, complaining about something not working or broken or missing. She kept on pointing to things for me to give her. She finally left but was still on her phone, she told me she would be home early, she told me to make something she liked, for once.

I texted Logan, I had to get dressed and begged him to come early to visit me. He was working but was going to stop by. I told him I had another hot fantasy outfit to show him, I would just have to change it before Linda got home. He was over before I hung up the phone.

I had a cheerleader outfit that I never wore, it was too revealing, too much of nothing. It was a white and cyan short tank top with a little matching skirt. My belly button would be exposed, along with my smooth stomach and hairless arms and shoulders. My body was now so much thinner I would look so cute in something like this, but it was an outfit for the bedroom, not the outside wooden deck. I put on sheer to waist pantyhose, no panties, I was thinking I was an older slutty cheerleader. I tucked myself in and put on a small panty shield, just to keep me in place. I slipped into my five-inch white pumps with straps, I started talking to the woman in the mirror, she was as excited as I was. "This cheerleader doesn't wear sneakers," I told her, acting cute. "She is in charge, she's head cheerleader." I giggled, I was getting a little excited.

I went back to check myself, my makeup, I smiled, I licked my lips, I was finally ready. I was too sexy for a Wednesday mid-morning, but not too sexy for Logan. I flat ironed my hair, making it look so much longer. I had just a touch of makeup and red lipstick once again to match my nails. I grabbed my pom-poms and ran outside to practice my cheers. I wanted to do a Clasp, then a High-V, and end with my signature Touchdown motion. Maybe a handstand to show off my pantyhose and legs, but maybe not.

Once again the dog rested quietly while Logan watched me from the bench. I don't think he was quite ready for this presentation, my moves, my outfit. He didn't move.

"Well?" I asked, my hands on my hips. He was still a little frozen, his mouth was open. I threw my pom-poms at him and ran. I hid from him behind the table, we went back and forth each gaining just a little bit of distance from the other. We laughed, we ran, I was having too much fun. I was making so much noise in my heels. He called the dog and Merch slid around my legs, I was disoriented, I held onto one of the deck chairs, I looked up and suddenly Logan was holding me.

"I win."

He picked me up and held me in his arms, I kissed him. He was so strong, I was so light. Then he walked back over to the bench and I plopped on top of him again. He held my nyloned thigh. Merch jumped up next to us. I had my head on Logan's shoulder, he kissed my cheek, he started to rub my breasts. He went under the tank top, started playing with me in my cute white sports bra, it was tight, he had trouble putting his hands under it. He squeezed and I felt him get hard under me.

"Is this a preview of things to come?" He whispered in my ear, kissing my neck, I rubbed his chest.

"No," I kissed him, his tongue entered my lips, "This is what's happening right now, don't drift away on me."

He laughed as I got on my knees, I pulled him out of his pants, I was great at this now. I sucked his cock once more hoping someone would come by to visit. I played with him again with my long nails. Logan moaned and I wished we had visitors behind me having drinks, maybe another couple looking for a good place to make love, maybe someone lost asking for directions. He came all over my top, I pumped and he shot. I tried to find it all with my fingers and then put it as sexy as I could in my mouth.

"I better change, I can't have Linda seeing me as a high school cheerleader with cum all over my uniform."

"Why not? You can tell her that's who you are now."

I thought he was being facetious, but he seemed quite serious. He took my hand and I sat back down on his lap.

"Maybe you are ready to become a cheerleader, a princess, anything. Maybe you are ready to just become you." He moved my hair out of my face, he put it over my ear, he was looking at me. His fingers traced my lips, my nose, my ears. "If you need me, I'm here. I will do anything for you." I put my arms around him and we kissed.

"I'm too scared, I don't want to say or do anything that will make my kids uncomfortable or Linda angry at me.."

"Okay."

"Unless..." I shook my head, I didn't know what I wanted or needed.

He smiled, we stood up. He rubbed my body, he held us together. He bent and kissed my breasts in the polyester. It was now his turn to get on his knees. His head under my short skirt, his face snug against my midriff, his hands on my ass.

"God, you feel so good, Sabrina. This feels amazing." And he then started to kiss my pubic area, I held on to his head as he kissed and licked. I never expected a man to ever do something like this to me, I was getting nervous, I had to get out of this outfit, I had to look presentable for Linda. "Mmm," He said as his tongue went below my crotch, just grazing the panty liner. "You taste fantastic, mmm." He moaned as he kneaded my ass, he pushed his face more into me. I started to feel light-headed, I messed up his hair, my whole body was gyrating, I was trying to hold on. I started to moan, I was making noise, I started to cum as he pushed his nose and chin and mouth around my soft mound. I felt my panties get wet from his saliva and my orgasm. I held him until I could breathe again. He was still licking and kissing me. I giggled and shook as he stood up, he then picked me up and carried me into my room, my heels grazing the walls, and we fell on the bed.

I was slightly on top of him, he looked very satisfied with this 'woman' in front of him, the skirt was high on her thighs. His hands were now on her face and hair again.

"Maybe, I am ready. Ready for whatever's next." He smiled, we talked for a while, he came up with a plan, just an idea.

I then had to get changed, I let him watch, while I found a more demure outfit. An outfit fit for an afternoon with the wife AND new boyfriend. Something to wear while I was serving drinks.