A New Start

After Deborah got her promotion, our entire situation changed. She began making far more money than we ever dreamed we would. She had been the breadwinner throughout our 2-year relationship, but with her new salary, my paltry income became unnecessary. One evening while she spooned me from behind, she whispered in my ear, "Sammy, I want you to quit your job tomorrow. I want you to stay home and start packing. We're going to be moving downtown."

It turned out she had been meeting with a realtor and had found the perfect condo for us. It was on the 14th floor of a building not far from her office. Those were the only details she would share with me. She refused to take me to the building so I could see our new home. She wanted it to be a surprise. She kept me away from it until the keys had been turned over and we officially owned it.

For the next three weeks, while she was at work, I packed up all of our belongings into boxes. During that same time, I always made sure I was freshly bathed and had a warm meal ready for her when she walked in the door after work. After she'd told me about her day and she'd eaten dinner, I went down on her and ate her to a relaxing orgasm or two. We'd snuggle up on the couch and talk or watch TV until we went to bed. When I'd go down on her once more before she fell asleep.

Deborah had been married once and her ex-husband was a jerk. From the few stories she shared, he didn't care much for foreplay and always left her messy with his ejaculate. She stopped enjoying traditional intercourse during that time. But she loved to be eaten. For a time, she thought she may be a lesbian or bisexual. But after she'd met me, she said she got the best possible solution to her sexual likes and dislikes.

Being a little more than a decade younger than Deborah's 34 years, I grew up always being the smallest kid in my classes and the last one picked for every sport I was forced to play. Being small shouldn't have been a surprise. My mother was very petite, standing two inches under five feet. After I'd stopped growing, I managed to top five feet, but just barely. I took after my mother in many ways. I got her eyes, her nose, her smile, her wavy blonde hair, and her petite build. After I'd gotten to my late teen years, my mother and I were often mistaken for sisters. It happened so often, we stopped correcting people.

Until I met Deborah, I'd never been with a girl, much less a woman. After we'd been together for a little while, we did make love. By then I was fully aware of how she felt about intercourse and let the foreplay last for more than an hour. I kissed every inch of her voluptuous body. I suckled from her breasts. I ate her to orgasm. I even tickled her brown button with the tip of my tongue. When I did finally slip my thin penis inside of her, I didn't last long at all. And knowing how much she disliked messes, I pulled out and squirted into my palm. While she lay there on her back, I knelt between her thick thighs squeezing out the last drips of my juice into my palm. Not having anything to clean up with nearby, I did what I'd done since I began masturbating, I raised my palm to my face and swallowed the evidence.

Deborah moaned while watching me slurp my juices up, "I love watching you do that." She didn't say any more until I'd finished cleaning up. She then pulled me into her arms, "If that was an example of what intercourse is going to be like with you, you've just changed my mind about it."

But I knew she'd been through a rough relationship and I wasn't the sort of person to push myself on her. I never instigated intercourse. I always waited for her to suggest it. But I really loved making her cum with my mouth, lips, and tongue. Or course I got wildly aroused while eating her. Sometimes she'd give me a fingerjob, I'm a bit too small for a handjob, she has big hands. During those fingerjobs, she liked to slip one of her fingers into my bottom. Other times I'd play with myself while she watched. After a long day, she'd sometimes fall asleep after I'd made her cum. Those nights I'm lay beside her and play with myself very slowly so I wouldn't shake the bed. But most times, I went without. I loved to make her feel good. And I never felt like I needed to cum.

I enjoyed being spooned from behind, in her embrace, with her taste on my lips, tremendously horny with a very stiff penis, while she slept. I truly enjoyed those nights where I struggled to think about how much I loved Deborah and horny I was. I tried to think of something to calm me down so I could go to sleep. That struggle always made me extra horny the next morning. Sometimes it went on for days and even weeks. But I didn't mind. When I did next cum, it was always a big one!

When Deborah returned from closing on the condo on the big day, I was waiting for her. That day I wore the outfit she most liked to see me in, white linen shorts with a relatively high waist and a mere inch-long inseam. She always said my butt was too cute to keep hidden behind baggy clothes, so those linen shorts fit snuggly. For that same reason, she also got rid of all my tighty-whiteys and replaced them with thongs and g-strings. Under those shorts, I wore a white g-string. The dress shirt I wore was matching white linen and just long enough to meet the waistband of my shorts. If I raised my arms, a strip of my pale midriff would be exposed. On my feet, I wore new, bright white, slip-on tennis shoes.

When she pulled up outside, I raced out to her car. After I'd jumped in, given her a kiss, told her I loved her, gotten buckled in, and began quizzing her on the closing, she placed her hand in my lap over my bump and said, "I love you too. You look lovely! The closing went smoothly, but I'm tired of signing my name."

Deborah often used words like lovely, delightful, cute, and pretty when complimenting my appearance. Every time she did, I felt a warmth in my chest and a tingle in my penis.

During the drive to our new home, I quizzed her on what our condo was like. But she continued to refuse to tell me even the smallest detail about our new home. While she drove us into the city, the buildings around us grew in height. By the time we'd gotten to our new building and Deborah had found our space in the parking garage, she grabbed her purse before coming around to open my door. She had always insisted on opening doors for me and it never failed to make me feel special.

She held my hand protectively while leading me into the building. She guided us to a bank of four elevators, pressed the up button, and we waited for it to arrive. A moment later, the doors opened and we boarded the vacant elevator. She pressed the button for the 14th floor before turning to face me standing against the back wall. She crossed the elevator and after taking hold of my hands in her, she pinned me against the wall and pressed her thick thigh between my legs. She kissed me with a level of passion I'd never experienced before. When our lips smacked apart, she bit my upper lip before moaning, "I'm going to take such good care of you."

I couldn't resist grinding myself against her thigh while I whimpered softly, "I love you so much."

When the elevator began to slow its ascent, we quickly broke apart and tried to look innocent before the doors opened. When they did slide open on the 14th floor, we found we were still alone. Deborah took hold of my hand and while leading me out of the elevator and down the hall, she told me, "In the four times I've been here, I've only seen one other person in the elevator."

When we got to our door, she slipped the key into the lock and opened the door. But she didn't let me rush inside. No, instead, she threw her purse inside before leaning down and scooping me up into her arms. She carried me across the threshold into our new home! After I'd looped my arms around her neck, I squealed, "This must be what a bride feels like!"

Deborah stared down into my eyes and stopped walking, in a perfectly serious voice she said, "Maybe the next time I carry you over that threshold you'll be wearing a wedding gown and we'll be coming home from our reception."

We'd talked about marriage before. During those talks, Deborah always said I'd look cuter in a gown than she would. She said clothes for petite girls were always cuter and sexier than the larger sizes she had to shop for. During one of those conversations, I admitted that I often fantasized about being a bride. She immediately agreed, she likes the idea too, a lot!

Staring back into her eyes, I whispered, "I'd love that."

She smiled before breaking eye contact and began walking further into our new home. She eventually set me down onto my feet and I sank into the carpet! I giggled while slipping off my shoes before she started the tour. There were two bedrooms, the larger of them was ours. Off of our bedroom was a large bathroom with a walk-in shower easily big enough for both of us. There was also a huge, walk-in closet. One of the three sides was a little smaller than the other two, while pointing at that end of the closet, she grinned down at me, "This is where we'll keep your clothes." She then pointed to the largest side of all three walls, "And this is where we're going to keep your wardrobe of girl clothes that I'm going to buy for you."

I was speechless. We'd talked about crossdressing quite often. She knew deep down inside I was a sissy boy. The thongs and g-strings I wore every day had tags from a lingerie store and I had several nighties I wore regularly. But she knew I'd always dreamed of dressing up all the way, all the time. Deborah had often said I would make a perfect young lady with my petite build and timid demeanor. And as I stood there looking up into her eyes, I asked a silly question, "Really?"

She leaned down, kissed the tip of my nose, "Yes, really. Sammy, I know how much you want this. And I want you to have this. I want you to be my little girlfriend!"

I whimpered softly and would have begun to cry if she hadn't pulled me from the closet and continued the tour. She walked me through the spare room, the second bathroom, the kitchen, dining area, and the tour came to an end in the massive living space. It was a huge room with one wall made from glass looking out onto the neighboring buildings.

When I tiptoed to the enormous window the length of the room and from floor to ceiling, I stood back a step and tried to peer down to the street. Deborah moved in from behind and wrapped her arms around me. She kissed up and down the side of my neck while unbuttoning my shirt. When the last button was opened, I spun around and giggled, "What are you doing?" She didn't respond. I squirmed with my back against the glass and squeaked, "But there are all those windows! Anyone could be watching!"

She slid my shirt off my shoulders and let it fall to the floor before going to work on my shorts. "Sami with an 'i', I've wanted to make love to you in front of this window since the first time I saw this room."

After the button on my shorts had been popped open, she slid the zipper down before slowly sliding my shorts down my legs. Her mention of love-making made me momentary forget about the enormous window I was standing in front of. "Like make love? Like penetration?"

While stepping out of shorts, Deborah picked up all my clothes and tossed them behind her. When she was standing in front of me again, she kissed my lips and whispered, "Yes, penetration. But I won't be the one being penetrated."

She hooked her thumbs under the bands of my g-string. I looped my arms around her neck, kissed her lips, and moaned, "You bought a strap-on?"

Deborah pulled my g-string up tight into the crease between my cheeks and over my penis. She moaned, "Yes, it's long and thin, and I know you're going to love it."

She didn't slide my g-string down my legs. No, she ripped it off my body. She'd never done that before. It didn't hurt. On the contrary, I found it to be a very sexy thing to do. I squirmed, naked with my back against the window as she kissed me passionately while sliding her tongue deep into my mouth. When that kiss came to an end, she stepped to her purse. From her bag, she pulled out a sturdy-looking harness with a long, thin pink dildo attached to it. On the end of the dildo was a slightly larger ball shape. I moaned softly when she began to pull it on over her pants.

She adjusted the harnesses before saying, "Turn around Sami with an 'i', look out the window."

I turned without even thinking about it. It wasn't until I was facing the buildings outside with their hundreds of windows all facing where I stood, that it dawned on me that I was naked in front of all of them! I'd been so caught up in the moment, I almost forgot about them. But as I stood there, scanning through all those windows, it became utterly clear that there had to be someone out there watching me!

When I covered my erection and took a small step back away from the window, Deborah spoke from behind me, "No, do not move away from that window. Sami, I've been dreaming about this for weeks! I'm going to make love to you right there in front of that window."

I didn't look back, I stepped back toward the window and rested both hands against the glass. Forcing myself to expose my naked body to anyone who may be looking. My eyes darted from window to window searching for any faces. I hadn't seen anyone by the time Deborah crossed the room, kissed my naked back before slipping a lubricant-covered finger between my cheeks.

I squealed and jumped up on my tiptoes! "You could have warned me you were going to do that!"

She kissed my back again, "Relax, Sweetheart. I want you extra slippery for this. This is going to be different from those times I've fingered you."

While keeping my hands on the window, I stepped away from the glass, arched my back deeply, and rolled my hips up to give her the best angle. My hips began grinding around when she slipped first one finger and then two inside of me. She eventually added a third finger and let me adjust to that before she withdrew them all.

I stood there, still scanning from window to window looking for anyone watching us. Thankfully, I hadn't found anyone. But just standing there was wildly arousing. Imagining all those windows filled with people's faces, watching what was happing in our window, made my heart race and my penis drip. Deborah soon leaned over my body and kissed the side of my neck, she whispered, "I love you, Sweetie."

I half-moaned, "I love you more!"

The next moment, I felt her hand on my bare hip, and then the slippery ball of the dildo pressing between my cheeks looking for its destination. When that well-lubricated ball bumped against my balloon-knot, I squeaked and arched my back deeper. Deborah took her time and didn't rush it all. Almost too often, she paused to ask if I was okay. I always told her I was wonderful. The only twinge of discomfort I felt was when my little hole stretched over the widest part of that ball. After it slipped inside, that pain was gone. Inch-by-inch, she slid the dildo into my body. After each inch, she asked if I was okay.

I finally craned my neck around and moaned, "I'm fine! I promise I'll tell you if it hurts. Just keep going! It feels amazing! I love it!"

At one point she stopped, "Baby, that's about half of it. It's really deep inside of you."

I gasped, "Keep going, please! Don't stop!"

She let little bits enter me and paused in-between, but didn't ask if I was okay. I soon found myself pushing back against her hips. The last several inches dove into me in one push. I moaned and arched my goosebump-covered back.

Deborah moaned, "You took it all! I didn't think you'd be able to. It's so long. But you did it. My God, you are so sexy!"

While still pushing back against the harness, I moaned, "Please make love to me, Deborah."

She was tentative at first, just small, gentle thrusts. I knew she didn't want to hurt me, she was just being careful. But I wanted more. I needed more.

I found myself moaning, "Don't tease me." I then rolled my hips forward and moved my hips toward the window which let the dildo slide out of me far more than she had let it. I then slid back at an even pace until it was buried inside of me again.

Deborah took the hint and began taking much of the dildo out before sliding it back inside. At the same time, she groaned, "Sami with an 'i' is a little tart!"

I moaned, "I'm your little tart!" A wave of goosebumps washed over my body and I shivered before managing to say, "It feels so good, Deborah! I like this way more than I thought I would!"

With those words, she pulled the dildo out to the ball. She then drove its entire length back inside of me. "I love it too, Sami." She began repeating that long, deep thrust into my body and I found myself pushing back to meet each of those thrusts. With each thrust, I felt a rush of joy. It quickly became clear that was the way I was intended to receive pleasure from the woman I loved.

She continued to slide that dildo in and out of my quivering body for a good long time, she even stopped to add more lubricant twice. During that time, I did see a few people pass by their windows. And I did see one man looking out his for a short time. By that time, I was hoping they would look over and see us! But no one ever did.

At one point along the way, Deborah groaned, "How is your little wee-wee doing?" She then reached around my hip and barely bumped it with her index finger. And that was all it took. It had been over a week since I'd last squirted which made that orgasm extra intense. My creamy juices shot out of my skinny penis at speed and the first surge splashed on the window. I managed to get my hand down there in time to catch the next three bursts of my love.

While I crested in orgasm and was still squirting, Deborah never slowed, she gripped both of my hips and continued to make love to me while I spasmed, twitched, gasped for breaths, and rode out the most powerful orgasm of my 21 years. She kept thrusting into me while I swallowed the small amount of my cream I managed to catch. That afternoon, my penis didn't go soft after squirting. It remained perfectly stiff while Deborah slid that dildo in and out of me, making love to me for the first time.

She eventually grew tired from the exertion and had to stop. After she'd slowly pulled the entire dildo from inside of me, I spun around and helped her to remove the harness. I then rushed it to the bathroom. While I cleaned up the dildo in the sink, Deborah entered the room and stepped behind me. After I'd finished cleaning it, she reached down and took my stiff penis between her finger and thumb. She whispered in my ear, "You should go pee, Sami. We don't want you getting another bladder infection."

As I slipped from her arms and moved to the toilet, she spoke up, "Sami with an 'i', in this house you'll always go potty sitting down. That's how girls do it and that's how you'll do it. Do you understand me, young lady?"

I giggled while raising the lid. I was going to enjoy the plans Deborah had for me at our new home. I sat down on the seat. Deborah moved in close, and I spread my bare legs wide to make room for her. She reached out and placed two fingers onto my rigid penis. She gently pointed it down into the bowl while whispering, "I'll get this for you."

I had to arch my back deeply and roll my shoulders back so my erection could be pointed into the bowl. Bracing myself on the toilet just behind me, I immediately knew it was going to be difficult to relax enough to pee.

It may sound strange, but it was a very tender moment. My legs were spread wide apart as I balanced on the toilet. I looked into Deborah's eyes and struggled to relax enough to go pee. But I'd never gone to the bathroom like that before. I'd never looked into someone's eyes while trying to go. I'd never had someone touching my penis while I was trying to go. I really struggled to relax.