The next weeks, months and years were then filled with bliss exploring my Sister's clothes, as she was happy to let me do. Being alone, or with my sister, many afternoons in the house allowed me to really get into the part. I remember a typical afternoon when I would immediately take off all my clothes upon arriving home. I would the start by putting on makeup at my sisters dresser, which had a mirror on top. It was nice to start out in the mirror with those fabulous eyeliners and shadows, mascara, and that sumptuous lipstick. This got me started already; with the heat beginning in my balls, ever so gently, then staring at myself hard in the mirror. Then I might decide upon a gorgeous corset with lots of lace, which I loved, and garters of course. I liked a hot red corset to match my lipstick, with black garters. Fastening that around me would send shivers up my spine; and through my cock, which would begin to stir. Rolling up those fabulous old-fashioned nylons and attaching the garters sent me off into an erotic realm from which I wouldn't return for a few hours. Pulling the bikini panties up over those nylons, feeling their material slide against the nylons, feeling my legs rub against one another in those stockings made me hard enough that the panties wouldn't quite cover my cock, the head of which was constantly peering out over the band. I would lick my fingers and stroke my cock-head with the spittle as a starter. Remembering my sister sucking on her boyfriends gorgeous cock would send me into a fantasy of sucking a cock while dressed the way I was. Fortunately, my sister had a couple of sex toys in her dresser, one of which was a dildo that looked just like a big cock. I would get this out and start sucking on it just as my sister had instructed me, starting with my tongue on it's head and practicing taking as much of that shaft as I could. At the same time I would start stroking my own shaft, my hand full of K-Y jelly. Having that dildo in my mouth and moving it in and out, imagining that my sisters boyfriend was fucking my face, would make me extra hot. I might imagine him saying something like, "OOHHHH, Tina, you suck me so great, your even better than your sister. Oh FUCK I'M CUMMING!" and I would, of course, be able to swallow his whole load! Soon I would be spurting cum all over the floor in front of me for the first time that day. Then something happened that really changed things. A few months after I had cum out of the closet with my sisters help, I had started to experiment with stimulating my ass. At first, of course, it was my finger, and then fingers that would probe my asshole, coated with oil or jelly. This felt so good to me, as I know it does to everybody if they just allow themselves the pleasure. I could, and did, spend a long time luxuriating in the sensations I felt when rubbing myself right around the opening of my ass and then deeper toward the prostate. Uhmm, what a great discovery! Then I tried to find the ideal object around the house that would help me explore more of this pleasure. My sisters dildo was a bit too big for this purpose, I didn't want to have to get past pain at that point. I did, however, discover my first true lover in our bathroom plunger! It was an easy size to take up my ass without pain and I could fasten it to the trim work next to the door so that it would stick out horizontally. Oh how I loved setting up the full length mirror opposite me and backing my ass up onto that plunger shaft dressed in her lingerie, or short dresses, or cheerleader outfit, or the sexiest combination I could imagine, staring at myself in the mirror, starting to ride that shaft in and out while I began stroking my rigid cock. I might say something like, " that's it Seth, Fuck me in the ass! I always knew you wanted to! Fuck me hard!....YESSS!" and I would spurt my jism once more, sometimes without even stroking myself!
It was during one of these sessions; looking at myself in the mirror, impaling myself on that plunger, that I noticed something that wasn't quite right. I saw a movement at the window that was visible in the corner of the mirror. Shit! it was Randy the kid from next door, and he was watching me! As soon as I met his eyes he turned and ran away. Oh my God, will he tell everyone in the neighborhood about what he saw? I thought I noticed that he had a hand down around his crotch. Was he getting turned on? I liked Randy, though he was a few years older than me and I didn't know him real well. He was on the swim team so I didn't run into him after school for a lot of the year. He also seemed shy, which was probably in my favor given the situation. The more I thought about him, the more I remembered how beautifully formed he was, in the way that swimming seems to do to people's bodies. He was about 6' tall with those lithe and strong muscles, olive skin, dark wavy hair, full lips; almost a Hungarian sort of look. Rather than wait and hope he wouldn't spread the word I took the direct approach that very next day. Normally Randy sat with a few of his friends toward the back of the school bus and I sat with a few of mine in the front. Our houses were near the end of the route so most of the bus would be empty by the time we reached home. So that next day I summoned up all the courage I could muster and went back to sit next to Randy. With a nearly parched throat I managed to blurt out, "Hi Randy, I know seeing me like that yesterday must have been a real shocker, I hope we can still be OK with each other. I mean I hope I didn't weird you out too much." Randy got real uncomfortable at this point and started staring out the window rather than look at me. He finally managed to speak, "Well it was pretty weird you know." was all he could say. "I know", I said, "but for some reason I really like to dress up like that. It gets me so turned on." "It did look like you were enjoying yourself, I'll say that." Randy replied. "What about you Randy, did you like what you were seeing?", I couldn't believe the words that were coming out of my mouth, jees Tina, you are pushing it. "Well, like I said, it was weird, but...... you do make a pretty sexy looking girl." Ahh, music to my ears! I was being swept away. "Hmm, well, if you'd like you can come over and see me today, I'd love to dress up for you." I said, licking my lips. "Well, I don't know Todd, this is all so sudden." Randy said. "That's OK. I tell you what, if you want to just let yourself in the house about a half hour from now and come on downstairs. My sister has practice today and won't be home till late. No pressure, I'll understand if you dont." With that, the bus arrived at our stop and we walked to our respective houses. This was way too good to be true. Even if Randy didn't come over, at least it seemed like he wouldn't tell the entire neighborhood about me. I sprung into action, which for me meant whipping off these boy clothes as quickly as possible and sitting myself in front of the mirror where I began to apply my usual deep red lipstick. I did want my lips to stand out for him after all- I wanted so much for him to get hard looking at me so that I could wrap these painted lips around his shaft. These were my thoughts as I coated my lips with that wonderful stick. My own cock began to stiffen, so I gave it a few loving strokes to get things started. I followed the lipstick with mascara and a touch of blue eyeliner. I thought I might keep it simple this time and wear my sister's babydoll outfit, which was a delicate peach color and had a very small bikini. I knew my cock would stick out of it a lot, but maybe Randy might like that. I pulled on some thigh-high off white stockings with lovely lacy elastic at the top to hold them up. I turned the lights down low enough to get a more romantic feeling in the room. I was barely done when I heard the door open upstairs and footsteps heading toward the basement door. What a gorgeous sight as Randy descended the stairs, he was wearing just his athletic shorts and a tank top, looking just like a god to me. "I decided I wanted to get a closer look." he said. "I'm so glad you did Randy" I replied, "come a little closer and look all you want." Slowly turning in a little circle I let him take me in with his eyes. Stopping with my back to him and raising the baby doll a bit, I couldn't resist asking "Do you like the way my ass looks in my panties?" "Ummhh......", was all he could say. "Go ahead and touch it if you'd like, it feels good." With that, Randy came forward and gently touched my cute little pantied ass for the first time of many to come. Feeling the pressure of his fingers sent a jolt of excitement through me and I could feel my cock jump in it's sexy nest. He gently moved his fingers, just barely touching me, taking his sweet time caressing my bottom. "Do you mind if I touch yours too?", I asked, turning toward him. "No, I don't mind..." he said. I began to feel his ass through his shorts as he contiued to stroke mine and I realized that he had no underwear on. I also realized that his hard cock was now pressing against my belly as we began to pull each other closer. This was my first sensation of another cock and I knew I would always savour the feeling. As he continued to stroke; and then squeeze my ass through my panties, rubbing himself against my belly at the same time, I brought one of my hands around under his shorts and began to gently squeeze his balls. This seemed to have the desired effect, as he began to moan in pleasure. "Uhhmmm, yes that's great." he said. "Randy, I'm going to suck on your cock now," I whispered in his ear. And indeed, I did as I had been practicing for months now, swirling my tongue around the head of his cock, keeping a tight grip on his balls, slowly stroking his shaft with my fingers, luxuriating in the sensation of a real cock going in and out between my pursed lips, the feel of it, so stiff and supple at the same time. Ohh, it was too good to be true! Now he rested his hands on the back of my head, not insistent, but a nice steady pressure, as I started to swallow more and more of his shaft; being aware of my own hard dick escaping it's panties and the feel of my stockings against the floor. 'OOHHHhh, FUCK, You suck cock sooo goooooddddd!!!" he managed to yell, as he started to fuck my face in earnest now, rocking his hips and thrusting his cock deeper inside my willing mouth. I was being face-fucked like I had seen my sister and I was loving every second of it, my little cock almost cumming on it's own as he exclaimed, "Ohhh SHIT, I'MM CUMMINGGGG!" With that his warm cum began to fill my mouth, as I started to swallow as much as I could, the remainder seeping back out past my sexily painted lips onto the baby doll I was wearing. "God, this is so FUCKING Hot!" I managed to blurt out, with a mouthful of Randy's cum muffling my words. I sprawled back on my sister's bed, knowing that I needed to cum in the best way. I started stroking my shaft and squeezing my balls as hard as I could when I felt another sensation, Randy was stroking my legs, focusing on that area right at the lacy tops of my stockings. "Oh, Randy, thank you, that feels real good", I said, continuing to stroke myself. He then moved his hands higher, underneath my panties, moving up my thighs. This had the effect of pulling my panties tight around my ass, and he started rhythmically tugging on the material of those panties where they went around my hips, pulling them up into my asscrack, stimulating me in a most delicious way. I was close to cumming when Randy put his hands over mine and gently pulled them away. The next sensations sent me into ecstacy, as I felt his hot lips engulf the head of my dick. He moved his strong hands around to my ass and started squeezing my asscheeks as he pulled my hips up and my hard cock into his mouth. Within a few rides in and out of his beautiful mouth I was cumming as hard as I ever had. "YESSSS! Randy I'm Cumming!" , I said, stating the obvious. Yet he kept at it for many more strokes, swallowing my cum as he pulled me in and out of his mouth. Sliding up along side me on the bed he began to kiss me, licking my lips at first and gently, but firmly, sticking his tongue into my mouth where the taste of both my cum and his mingled together. Being kissed by a boy for the first time, sucking his tongue deep into my mouth, made me want to cry. We held each other close and drifted off into the bliss of afterglow and sleep.
Awakening, with Randy still asleep, I had an idea, sort of a delicious surprise that I hoped he would like. It would take me a few minutes to get ready, but it looked like he'd sleep for a little while. I managed to get ready and quietly lay down next to Randy once more on the bed. I turned toward him and started nibbling on his ear to waken him. He began to stir and when it seemed like he was awake I whispered in his ear, "Randy, I'm still a virgin until you fuck me. Would you like to fuck me now?" "Well. Todd, I don't......" , he started, still looking up at the ceiling. "Call me Tina" I said. He looked over toward me with a questioning expression, and then amazement, as he saw that I was wearing a gorgeous snow white wedding gown! I had applied fresh makeup and was in the process of pulling up my gown to reveal white garters holding up pure white stockings. "I'm still a virgin Randy, why don't you fuck me? I know we'd both like it." I glanced at his cock which was getting harder by the second. Grabbing the K-Y jelly I had placed nearby I sat up and started smothering his shaft in it. I lay back down and smeared some on my asshole. He responded by rolling over onto me taking me into his arms. I lifted my legs as high as I could and he started rubbing his dick against me, at first right near my virgin asshole, but then the head of his cock was beginning to slowly push against my opening, working it's way inside. The pain began, slowly at first, but then sort of searing, as his big cock stretched my hole. At last it popped inside. "Ohhh!," I yelped, as my eyes filled with tesrs of pain and joy. He kissed away the tears as we lay still for a moment. How sweet he is, I thought. Then he began moving again, slowly, as the pain began to fade. I put my legs around his neck and he pulled me close as his hips began to pump that beautiful cock into me. I squeezed his ass and dug into them with my nails as he said, "Oh, Tina this is so fucking great! I love fucking you" "That's it Randy, fuck me as hard as you want, I'm yours!" With that, being a very strong boy, Randy stood up with me still impaled on his cock. I moved my legs to around his waist and he started lifting me up and down on my shaft. I no longer felt any pain and my cock had grown so hard between us. "Yes, that's it Randy, I love you fucking my ass!.......OOOOHHHHH!", I said, as the cum was suddenly sticky between our bellies. "Tina, I'm gonna cum in your ass......" "Yes, please Randy, fill me up like your bride!" Randy's strong hands around my ass kept riding me up and down his shaft, how incredibly strong he was. "Ohh, FUCK YESSSS!", he exclaimed as the cum started leaking out of my ass.
"God, that was so hot!" I heard, a voice, but not Randy's. I looked over at the stairs and there was Seth, his hard cock in his hand, staring right at us.