Boys in the Attic

The few days that followed were blissful. I dressed as often as I liked. I "relieved" myself as often as I could. My walking in heels improved. I was convinced I was hot. My fantasies of being "taken" by other guys grew more elaborate and stimulating. I had one explosive ejaculation after another. I slept very well at night, especially when I was wearing a lace teddy and stockings.

Joan returned in the second week of January. My idyllic mini vacation was over. I nearly cried when I saw her car pull into the driveway. Once she was unpacked and settled, Joan talked for a few hours about where she had been and what she had done. I was fascinated. I wanted very badly to spend a year abroad, but I didn't have the time nor the cash to do it. Joan's stories and photos were the next best thing.

Joan went back to work, Billy returned and the spring semester got underway. I dove headfirst into the new round of study and writing. I wanted to repeat my success of the last semester. I spent more hours in studying on the weekends. Even though I still had most of the money my folks had given me at Christmas time, I avoided spending it on dining out or drinking. I kept my nose to the grindstone.

Spring break rolled around much faster than I had imagined. The bitter cold of the winter receded and we had a few nice days in a row every week. It was great to be able to open the windows and air out the house. Joan's Easter break from her school coincided with the university's break. Joan told me that she was going to Florida for several days and asked me if I could watch the house. I immediately, happily agreed! Billy said that he was going to take a road trip to California. I was secretly ecstatic that I would again have another week in which to indulge my secret self.

As soon as my housemates were gone I rushed up to the attic. The temperature up there was perfect. Rather than make several trips up and down the attic stairway, I undressed in the attic and put on my female outfit there. I used the sofa for sitting as I dressed. It was clean and in decent shape. I wondered why Joan had left it there. I selected red again for my first session. Red undergarments and shoes. A red cocktail dress that felt wonderfully light on me. It had a bit of fringe along the hem that seemed very sexy to me. I loved red on women. I loved it on myself! I tried dancing; nothing fancy: just a few moves moves I knew that were manageable in heels. I started singing a pop tune that was then at the top of the charts. I giggled at the sound of my own voice. The sound of clapping froze the laugh in my throat.

I turned to see a young man standing on the stairway. His chest and shoulders were just above the level of the attic floor. Of course I was shocked and humiliated, but I did notice that he was quite good looking. I scrambled to think of an explanation.

"Don't let me interrupt," he said with a laugh. "That was very entertaining."

My face must have been as red as my outfit. "Who are you?" I asked.

"I'm Jerry. Joan's nephew. Didn't she tell you about me?" Jerry ascended the rest of the steps and stood just a few feet from me. He was taller than Joan. I guessed he was six-four. I also guessed that he was a football player or on a hockey team. He was powerfully built. I was doubly humiliated to be dressed in front of a much larger guy.

"No, she didn't," I said. "How did you get in?"

Jerry took a set of keys from his pocket. "I've always had a house key. I stay here in the summer's and help Aunt Joan with her gardening. Right now I'm studying up at Buffalo, but now I'm on my break. Are you Dale?"

I was so embarrassed. I had to nod, but I started crying as I did. The shame was just too much. My body stooped as I bawled. Jerry closed the space between us and gave me a hug. I felt as though a grizzly bear had taken me in its arms. Without thinking, I rested my head against his rock hard chest.

"It's okay," Jerry said. "I'm sorry I surprised you. I was passing through town on my way to the city, and I had asked Aunt Joan if I could stop by here for a rest. I guess she didn't tell you."

I shook my head and croaked "No. She didn't. Please..."

Jerry patted me on the back. "Don't worry. I won't tell anybody." He pushed me back slightly and looked at my face. "You know, you look really nice in those things."

I couldn't meet his eyes. "I'll change. Just give me a minute." I started to turn, but Jerry held on to me.

"Why change? You're doing what you like to do. Don't let me stop you." He kept a soft grip on my biceps.

How could this have happened? I thought I had always been so careful. I was naive. I had allowed myself to become too distracted to pay any attention to the world outside the attic. A marching band could have walked through the first floor and I wouldn't have noticed. Now, my secret was a secret no longer. I wanted to disappear into a puff of smoke. After a few moments I looked at Jerry's face. He had a kind, empathetic smile.

"Jerry, I can't stay dressed like this. It's too embarrassing. If you'll just give me a few minutes, I'll meet you downstairs in my real clothes. Okay?"

Jerry answered by moving me back to the sofa. I felt helpless to stop him. At his unspoken request I sat down. He sat quite close to me. Our knees touched. Jerry put his right arm on the back of the sofa. A slight thrill raced through every part of me.

Jerry's voice soothed my frayed nerves. "Look, I'm not out to get you into trouble, okay? I won't say a word to anybody. What you do up here is your own business. It's not for me to stop you, or to expose you."

I shook my head. "I don't know why I do it. This really isn't me. It was just that one day I was up here and I saw the clothes. I couldn't help myself. I only do it when nobody else is around."

I felt Jerry's hand around my right shoulder. It felt good, I have to say. I felt the fabric of the dress between his skin and mine. In fact, every bit of clothing I had on at that moment seemed to come alive and excite me. It scared me a little.

"Do you have a female name, Dale?" Jerry asked.

It had never occurred to me to name my other self. I shook my head.

"You know, Dale can go either way." Jerry maintained his kind smile. "But maybe you'd like something that's totally different." He placed his left hand fingertips against my left leg. I nearly jumped!

"Um," I began, "I really can't think of anything off the top of my head." I hoped that Jerry wouldn't spot the little tent in my dress.

Jerry looked away for a second. "Let's see," he mused. "How about...Tracy?" He looked at me for my reaction.

I liked it! I also liked that I didn't have to spend any more time looking like an air headed girl. "Tracy's nice," I said.

"Good! Tracy it is. Let me hold your hand, Tracy." Jerry lifted his left hand slightly. I gave him a wary look, then placed my left hand in his. Again I had the feeling of a bear's claw encircling my too-small hand. But it was wonderful! He was so handsome, and he smelled like he had just stepped out of a hot shower. I lowered my head and giggled!

"How old are you, Tracy?" Jerry started stroking my palm with his fingertip as he spoke.

"Twenty-one." I whispered.

"I'm eighteen," he said. "I'm still a freshman. I guess that makes you an older woman?"

I laughed softly. "I guess it does." What the hell was happening? Was he really trying to seduce me? I didn't know how to get myself out of this predicament. "Do you mind that I'm older?"

Jerry chuckled. "Not at all. I like older women. You know what?"

I shook my head. "No?"

"I like older men, too." Jerry's gaze transfixed me.

I was speechless. My mind raced through all of the possibilities. He was gay? Bisexual? Was he really serious now? I must have had a look of sheer panic. Jerry released my hand and placed his palm along my right cheek. He leaned in toward me. Oh no. No. His lips touched mine. I closed my eyes.

Yes, dear readers, it was my first kiss. Laugh if you must. I was THE high school geek. College geek. Geek of all pocket protector geeks. I had had crushes on girls from puberty onward, but I had never been able to summon the courage to actually ask one out on a date. As I have mentioned, I also had boy crushes on some of my classmates. Doing anything about it was unthinkable. I had always believed that my first kiss would be mine to deliver; delivered to the lips of a sweet young girl who would eventually become my bride. And now this.

Not that it was bad! I found myself quickly opening my lips to receive Jerry's probing tongue. We licked at each other and took playful bites at each others' lips. I noticed that his right hand was completely around my right side. The warmth of his other hand against my cheek was delicious. Nothing I had ever experienced in the past felt anywhere near as good.

Jerry pulled back just far enough to give me a broad smile. "You're a great kisser," he said. He caressed my forehead with his thumb. "Lots of practice with coeds?"

I whispered "No. You're my first." I hated myself for admitting it, but this gorgeous hunk of a young man had me under his spell.

"Are you serious?" Jerry said it without making me feel bad. "I would have never guessed."

I had to feel his lips again. I leaned up and resumed our kissing. Jerry moved me back a little and brought my legs up over his lap. He held me with his right arm and caressed my lower legs with his other hand. This was too good to be true! Shock waves traveled from every place where his hand met my nylon covered legs. He had me. I would do anything for him. Any hesitation I had ever felt about being with a guy was gone. If I was to lose my virginity to a man, so be it.

Jerry pulled back his right arm slowly and allowed me to rest against the arm of the sofa. I lifted my legs as he stood up and started taking off his shirt. I was entranced. His upper body was perfectly formed. He had abs to die for. Jerry's arms were heavily muscled. This was the first time I had realized just how sexy a male body could be. Jerry kicked off his loafers and pulled off his socks. His jeans dropped and I saw the outline of his cock against his briefs. It wasn't huge, but it made a nice bulge. After he stepped out his jeans, I sat up on the sofa and motioned for him to stop.

"Let me do the rest," I said in my best sultry voice. Jerry grinned and stepped forward. I started by running my palms over his chest and stomach. It was as if he were made of polished marble. I traced the bulges and the crevices. I stopped when I reached the waistband of his briefs. I looked up. "Are you sure?"

Jerry didn't speak. He just winked and nodded. He caressed my hair with his giant hand.

I continued. I hooked my fingertips under the waistband and pulled down. The front of the shorts caught on his cock. I pulled them forward and saw my prize spring up just inches from my face. It was thick and possessed a large, perfectly formed head. I was giddy. I don't think I fully understood what I was getting into, but it seemed like a good idea! I took his cock in my right hand and cooed at its feel. Jerry moaned.

You may find all of this very hard to believe. I had arisen that morning as a straight, part-time cross-dresser as square as any other geek on earth. All I had wanted to do was to dress up and masturbate, now that I had the means and opportunity to do so. But now, just a few hours later, I was about to perform my first blow job. I suppose stranger things have happened, but I can't think of any. You just have to believe that I - in that moment - was completely taken in by Jerry's charms and his self-confidence. His size, as well. I thought of myself as a pretty cheerleader to his alpha-male quarterback.

My lips touched the head of his cock. I opened my mouth and licked the spongy head. It was wonderful! Before long I was bathing every bit of his tool with my tongue. It was in and out of my mouth, as were his balls. I stroked him and tickled the underside of his cock with my fingertip. Every so often I would look up and delight in his smile. Then I would look down at my red shoes and red-tinted legs. This could not possibly be real! But it was.

When Jerry was about to come I felt his cock swell a bit. He grunted and I prepared myself for the semen spray. Several spurts of cum hit the top of my mouth as I licked the bottom of the head. I kept all of the semen in my mouth. I wasn't crazy about the flavor, but I didn't gag. I swallowed it and licked his cock as it slowly shrank. Jerry panted and collapsed on the couch. I giggled.

"Was I good?" I asked.

Jerry took my hand and kissed it. "Unbelievable," he answered. "My god, that was good!" He pulled me over for a kiss.

We played dueling tongues for a bit. Jerry's hands were all over my body. When he touched my privates I squealed. At last, I stood and twirled for him. Jerry's grin said it all.

"Take it off," Jerry growled.

I played dumb. "Who, me?"

"Who else? Come on. I want to see what's underneath that dress."

I felt a moment of insecurity. "Jerry, I'm happy just to do stuff for you. To you."

Jerry shook his head. "Nope. We've just started. Turn around."

I obeyed. I felt Jerry unzip the dress. I let it drop. His hands cupped my ass cheeks. I squealed again. He turned me around to face him. My lace panties and garter belt felt even better as they were exposed to his examination. Jerry pulled me forward and kissed my tummy. I giggled. He surprised me by standing and lifting me into his massive arms. What did he have in mind?

Jerry answered my unspoken question by carrying me down to the second floor. I was a doll in his arms. I felt weightless. He opened Joan's bedroom door and laid me down on her king-sized bed. I felt an added sense of naughtiness for being in there, but I was not about to object. Jerry opened a drawer of Joan's night table and took out a small packet. He put it on the bed next to us. "For later," he said.

Jerry then laid himself down next to me and covered my body with caresses and kisses. He took off my bra and kissed my nipples. He kissed my neck and my ear lobes. He stroked my legs and thighs. Jerry removed my panties and freed my straining little penis. He took it in his bear paw and nearly killed me with pleasure. As Jerry kissed me, he stroked me until I came all over his hand. I hugged him tightly and moaned into this mouth.

Jerry kissed my face and my neck as I recovered from my orgasm. I really was on a cloud at that point. Nothing existed beyond my arm's reach. My man was all. Jerry smiled at me and stroked my hair. He was so sweet! Every kiss of his convinced me that I was madly in love with this stud.

Before long, I once again felt Jerry's hard cock in my hand. He raised himself onto this knees and picked up the packet. He tore it open and poured a small amount of lubricant onto his cock. Was he...? Was this it? I was suddenly afraid.

"Don't worry," Jerry said. "Just relax and let me guide you. I promise it will be the best thing you've ever felt."

I was somewhat comforted by his words. Still...

Jerry remained on his knees as he pulled my legs around his waist. I scooted down until I felt his cock head against my asshole. Jerry spread a dollop of lubricant against my opening. I jumped and gasped. Jerry chuckled. "Ready?" he asked. I bit my lip and nodded.

Jerry was a master at deflowering me. There was quite a lot of pain at first, but he kept talking softly to me and assured me that the pain would pass. It did. An incredibly powerful feeling of sexual pleasure took its place. I can't do justice in words to how good it felt. My legs locked against Jerry's back and I felt my heels click together with each of his thrusts. This was my most treasured fantasy come true. My prince was taking me as his woman. He was going to satisfy himself in me, and I would enjoy every second of it. He grunted and I moaned in unison. When Jerry came I felt the most wonderful sensation of warmth and fullness in me. I imagined myself being impregnated by his release. That thought pushed me right over the edge. I sprayed a few spurts of cum against his belly.

We shared a many kisses in the minutes that followed. Jerry rolled to my side and I threw a leg over his. We laughed. I think we did all of the normal things any couple would do after such a passionate act. I was too happy and spent to worry about what I had just done. Then a stray, discouraging thought entered my mind. I raised myself on one elbow and brushed my hair from my eyes.

"Hey," I said, "don't you have to go to the city?"

Jerry chuckled. "Not really. I'd rather stay here."

"But I thought -"

Jerry cut me off by placing a fingertip on my lips. "Don't worry, doll. I was just going down there to see if I could meet a guy for some fun. I found a girl, instead."

I playfully slapped his arm. "Hey!" I said in as deep a voice as I could manage. We both broke up at that.

"Listen," Jerry said, "Why don't I call Aunt Joan and tell her I'm going to stay here for a few days? I'll tell her the truth: I met you and we hit it off. Besides, I'll save a hell of a lot of money on hotels this way. Sound good?"

"Are you kidding me? You mean you want to stay with me?" I was over the moon!

"Of course! Why not? I think we might have a little fun." Jerry squeezed my butt cheek with that remark.

"Yes!" I squealed, followed by a big wet kiss on his lips. "Just don't tell Joan what we're doing."

Jerry rolled his eyes. "First, she wouldn't care. Believe me. She knows I'm bi and it doesn't make a damn bit of difference to her. Second: as long as you want to keep it a secret, it's a secret. I'm not interested in hurting you in any way. Okay?"

"Alright," I replied. I kissed him again. "It'll just be a while - if ever - before I can even think of telling anybody else." he nodded. I laid my head on his chest and drew circles on his skin. Before long, we were both asleep.

The week that followed was the happiest of my life. I spent nearly all of it in Joan's old outfits. Every day was a fashion show for Jerry's amusement and arousal. We made love as often as we could, limited only by our stamina. Jerry proved to be a very thoughtful and gallant boyfriend. He even bought makeup for me! I would have died sooner than buy it for myself, but he walked right into the drug store and got me everything I needed to pretty myself up nicely. He explained that no one ever pays as much attention to us as we think. I couldn't agree, but I was thankful that he believed it. I practiced all day long with the brushes and applicators until I looked fairly good. I rewarded Jerry with all sorts of treats.

When the week came to a close I was heartbroken. I knew that I had fallen deeply in love with Jerry. I didn't say it, but I'm sure he knew it. We spent our last hour together just holding hands and talking. Jerry said that he would be back as often as he could manage it. I was so tempted to drop everything and move up to Buffalo with him, but I retained my desire to finish my undergrad work at Binghamton and get a scholarship to grad school. I explained this to him and he agreed fully.

We parted, and tears coursed down my cheeks as I watched his car disappear down the road. I was back in my male clothes, having returned all of Joan's clothes to their rightful place. It took hours for me to recover from my grief and focus my mind on my studies. Joan returned that night and asked me all about Jerry's stay. I didn't say much.

It was so hard to get back into the routine of classes and study. I managed it, but my heart was no longer fully in it. Most of my heart had been carried up to Buffalo. I longed for Jerry's touch during every waking moment. I knew that I had to get over him. First loves, I had heard, are always the hardest.