2 comments/ 7185 views/ 10 favorites Alone Time Ch. 02 By: bullockhall I awoke Sunday morning in my warm bed and stretched. I lay there for a moment, remembering the events of the night before. I had spent the evening dressed, as I usually did on Saturday, in beautiful, sexy lingerie. I had thought my crossdressing was a secret, particularly from my housemate Jack. As I lay on my bed in my female alter ego, pleasuring myself and dreaming of being taken by a real man, I had slowly come to the realization that I was not alone. I had heard soft noises coming from my closet, and figured out that my roommate had not gone out for the night but had hidden in my closet to watch me dress and masturbate. The idea that I was being watched by my friend was scary, but highly erotic. I had exploded in an earth shattering orgasm, and had found myself hoping I had pleased him. I rolled out of bed with the germ of an idea in my head. I hadn't told Jack about my crossdressing for fear of rejection. Clearly he had figured out my little secret and, rather than be repulsed, it turned him on. As I stood in front of the mirror brushing my teeth I thought about what that meant. I liked Jack, liked him a lot. I had never thought of him 'that way'. He was good looking, and friendly, and sweet...and sexy? If I was honest with myself, he was sexy, no doubt about it. I tightened the belt on my robe and headed downstairs. I walked into the kitchen and found Jack sitting at the kitchen table drinking coffee and reading the Sunday paper. He was wearing his usual gym shorts and tee shirt. He was sitting in one chair with his legs stretched out and resting on a second chair, the sports section open on his lap. As I walked over to the stove to put on some water for tea I admired his long shapely legs. Why had I never noticed them before? "Morning Jack!" Jack jumped in his chair and seemed to be avoiding eye contact. "Oh, sorry. Morning" he mumbled. He was staring at the paper so intently I thought it would burst into flames. I decided to let him off the hook. "So...I never heard you come in last night. You must have been out late, did you have a good time?" Jack visibly relaxed. He put the paper down and looked me in the eye for the first time this morning. A tiny smile played on his lips. "Yes, yes I did. It was, I don't know, different. But I really enjoyed it." "Different? You mean you and your buddies didn't do the same old, same old? Get drunk, tell dirty jokes, and annoy girls? Wait a minute...did you meet somebody? You did, didn't you? Tell me, tell me!" "Wellllllllll...I did, kinda, meet someone new. She's...different. Beautiful, sexy, but definitely different." "Different is good! I'm happy for you! It takes courage to step out of your comfort zone. Are you going to see her again?" Jack actually blushed. I was shocked...and mildly aroused. "Well, I hope to see her again. But I'm not sure. She's not like anyone else I've ever, you know, dated? My friends might not approve. I don't even know if she'd be interested in me." Don't worry about your friends. I've met them and most of them are, if I may be blunt, morons." Jack laughed, and smiled. "And you're a really nice guy. Any girl would be lucky to have you. Even if she's 'different'. Maybe especially so." My kettle began to whistle, and I got up and prepared my tea. Jack went back to his paper. I grabbed my tea, and a scone from the basket on the table, and headed for my room. I heard Jack's voice just before I left the room. "Do you really think so?" "What's that?" Jack sighed. "Do you really think any girl would be lucky to have me?" I almost made a joke, but I saw the look on his face. "Yes Jack. Yes I do. I know so." "Thanks. I appreciate it." The rest of the day went uneventfully. We watched NFL football, had a few beers, and generally relaxed. We talked about the games, laughed at each other's jokes, exchanged small talk. Overall, a good day. No mention was made of last night. Late afternoon, after the second game, I stood up and stretched. I collected the trash in the room and tossed it out. "Hey, Jack! I think I'm done for today, I'm all footballed out. I think I'll head upstairs, get cleaned up, get ready for tomorrow. You be ok?" "Yeah buddy. Go ahead. I might go out for a bit. See you later." I headed upstairs with a smile on my face. My body was tingling as I bathed. I scrubbed myself, paying particular attention to my bum and hole. I reshaved my entire body so I was smooth and hairless below my ears. I rubbed lotion over my entire body so I felt and smelled wonderful. I pulled on my robe and left the bathroom. Standing in the hall I listened for a few seconds but heard nobody in the house. Tip-toeing downstairs I peeked into the kitchen and living room. The tv was off and there was no sign of my roommate anywhere. Just like last night. I went back upstairs and entered my room. I dropped my robe on the floor and padded naked across the room. I sat down in front of my mirror and applied my makeup carefully, ending with bright red lipstick. I kept glancing in the mirror at the closet directly behind me, but never heard anything from there. Makeup done, I stood up and walked to my dresser and pulled out the new lingerie I had picked up yesterday. I held up the red corset in front of me and admired it. I loved the way it looked. Red satin body, soft breast cups, black lace trim and attached black stocking garters. I wrapped the corset around myself and connected the front closing hooks. I pulled two soft breast forms from the drawer. I held the up and looked at them. They were a B cup, I'm a crossdresser, not an exotic dancer. Applying a gentle adhesive to the backs I slipped them into the corset cups and adhered them to my sadly lacking chest. I turned and admired myself in the mirror. With my new breasts and makeup I was beginning to look like a beautiful woman...well...except for the fully erect penis that pointed at the mirror. Needed to do something about that! But first, stockings. I selected traditional sheer black silk stockings with the seam up the back. Expensive, but oh so sexy! I slipped them up my smooth legs and clipped them to the garters on the corset, careful to keep the seams straight. Then I pulled on the sheer black thong panties I had purchased. They weren't going to cover much, but I don't think I was really going for subtlety tonight. Next I reached under the bed and pulled out the box containing the wig I had selected earlier. It was my favorite. I called it my 'flapper' wig. It was black with straight hair coming to just below my ears. The ends curved, and pointed towards my mouth. It matched my outfit perfectly. I kneeled down on the floor to slide the box back underthe bed. While I was down there, with the bed between me and the closet, I found the tube of anal lube I had stored there and liberally lubricated my ass...just in case. Standing up, I looked directly at the closet for the first time. I announced aloud, as if in a warning... "Now where did I leave my favorite high heels? They must still be in the closet." I strode purposefully to the closet, tingling with excitement. I opened the right door and grabbed my favorite black patent leather stilettos with 4" heels. Facing away from the closet I stepped into the right shoe, the the left. Standing up straight, I admired myself in the mirror and took a deep breath. I was ready. Turning back to the closet, I grabbed the handle of the door on the left and ripped it open. I had been practicing my shocked expression all day for this moment. I didn't need it. The closet was empty. Jack wasn't in there. Nobody was in there. I walked sadly back to the bed and sat down. I felt like an idiot. How could I have been so wrong? Had I actually believed that Jack had wanted me? I felt a tear run down my cheek and I lay back on the bed. I felt depressed. I must have dozed off, because I snapped awake due to a knock on the door. I wiped my face and looked at the clock. More than an hour had passed! "Who is it?" "It's me...Jack." Oh shit, Jack! He must already think I'm nuts, and he'll know for sure if he sees me like this! "What do you want?" "I want to come in." "NO! I mean, what do you need, it's late." "Open the door please...I want to talk to you." I looked around, panicked. I could throw my robe on, but I was in full makeup. He would know. "I was getting ready for bed...I'm not dressed." I distinctly heard a sigh come from the hall. "Just open the door a crack. Please? I need to say something. After that, if you want me to leave, I will." I tiptoed over to the door, still in my high heels. I opened the door just an inch and stuck my eye to the crack. Jack stood there smiling at me. He held up his hands, showing me he brought a bottle of my favorite wine, and two glasses. "Yes?" "I told you this morning that I had met someone beautiful, sexy, and different. You said I should go for it. I'm going for it. Open the door. I want to see you...the real you." I was stunned. As if in a trance, I opened the door all the way and stepped back, giving Jack the full view of my outfit. Jack gasped, his jaw dropping. "You're...beautiful. No, I mean, perfect, you're perfect!" He held the wine and glasses out, and I took them from him. "Come on in." I seemed to be whispering, my voice suddenly hoarse. I turned and walked back into the room with Jack following. I placed the wine down on my dresser, acutely aware of how much ass was showing under my corset and above my stockings. I turned around, and Jack was right there, an inch from my face. In my heels I was the same height as Jack. Our lips were practically touching, our breathing ragged. He raised his hand and gently touched my face. I shivered. "May I?" I nodded dumbly. Jack pulled my face to his and our lips met. I melted, electricity coursing through my body. I wrapped my arms around his neck. He leaned into me, pinning me against the dresser. Our tongues explored each others mouths as Jack ran his hands all over my body. We broke our kiss, gasping for breath. "Wow!" Jack grinned at me. "Yeah. Wow!" I reached out to him and began unbuttoning his shirt. I slid it off his shoulders and ran my fingers over his hairy chest. Jack placed his hands under my ass and lifted me up. I wrapped my arms around his shoulders and my legs around his hips. He turned and carried me across the room and laid me down on my bed. Jack stood back and looked at me with passion. He stepped out of his shoes and pulled off his socks. As he undid his belt and pulled down his pants and underwear I moaned audibly. He smiled and stood in front of me completely naked, his hard cock pointing right at me, teasing me. I held my arms out to him, pleading. Jack climbed on the bed and I took him in my arms. I kissed him hungrily as I ran my hands over his back and down his ass. He ground his erection into my panty clad cock as I felt my precum soaking my panties. After several minutes of this I was ready to explode. Sensing this, Jack whispered in my ear. "What do you want my sweet?" "Oh, baby! I want you to fuck me!" Jack kissed my lips, then pulled away. He kissed my neck, my chest, my tits, my tummy. He finally settled his mouth over my groin, where he began kissing and nuzzling my cock through my panties. I writhed in pleasure. "Please baby! I want you inside me!" Grinning, Jack knelt beside me and took the sides of my thong in his hands. I lifted my legs and Jack slid the thong over my ass and up my legs. He sniffed it before tossing it aside. I spread my legs, showing him what was his. He ran his hand down my leg and across my ass. I moaned loudly. He stuck his finger in my asshole, finding it already lubed. If he was suprised, he didn't say. "Stop teasing baby, get over here!" I pulled him down on me and, grabbing his stiff cock, placed it against my slick hole. He eased the head of his cock into me, pausing to allow me to adjust to its size. I felt it stretch my hole, then ease as he withdrew. Again, a half inch further, then out. In again, and inch this time, and I pushed back against him, wanting him to take me. Suddenly he was in and I felt him fill me. I was in heaven! Jack was very gentle and I felt wonderful as his cock filled my ass to its length. I pulled his mouth to mine and wrapped him in my arms as he fucked me slowly, the faster. I put my feet, still in their high heels, behind his ass and pulled him deeper into me. His cock massaged my prostate and I was in ecstasy! I began shaking and bucking, and then burst in a massive orgasm. My body tingled as I spewed cum all over my belly and chest until I was done. Jack's breathing became ragged and I knew he was close. He started to pull out but I grabbed him and pulled him close. "Don't you dare leave! Stay inside me! I want to feel you!" Jack groaned and spasmed, slamming his cock into me as he came. I felt his warm seed filling me as he emptied his balls. Finally done, he pulled out, his cock slipping out of my ass with a 'plop'. I felt strangely empty as he rolled over next to me, breathing heavily. I lay may head on his chest, feeling spent and satified. After a few minutes, Jack rolled over to face me. I took his face in my hands and kissed him gently. "Thank you sweetie. That was wonderful. I didn't know what to expect when you knocked on my door." "No. Thank YOU! That was...indescribable! I've never felt anything like that! Nothing could top that!" "Nothing?" I grinned wickedly as I took his soft cock in my hand and stroked it. I bent down and ran my tongue along its length and felt it harden. "Let me see about that..."