I am 48 now, but this story takes place when I was a teenager. It is autobiographical.
This story is intended only for readers 18 and older. Feedback from readers is greatly appreciated!
From Brother to Lover--Part 2
That night, after pretending to work on my homework in my room (all the while actually reliving my first sexual contact with Bill that afternoon), I went downstairs and announced to my parents (loudly enough for Bill to hear in the other room) that I was going to take a shower and go to bed. I did this because my normal routine involved showering in the morning and I knew there'd be questions--I didn't want to be interrupted during my shower or intercepted on the way to my room. As anticipated, my parents asked why I was showering at night and I replied that I felt "grungy" and that, with Bill home, the shower schedule might be pretty congested in the morning.
I went upstairs, got undressed, and went into the bathroom, taking care to lock the door behind me. I had been thinking all night about what I could do to make myself as girly as possible in case Bill was interested, yet avoid being found out by my parents. I decided to settle for shaving my entire body very carefully in the shower--I hadn't much hair anyway. I also wanted to make sure my "pussy" was as clean as possible--just in case Bill wanted to explore it, so I turned around and cleaned myself with my fingers. I crouched and stuck my bottom up so that the hard spray from the shower head hit me just right--it felt heavenly, making me feel even more feminine!!! The shower was followed by a thorough, rose-scented moisturizing of my torso. I was too frightened to use any of my mother's make-up, save some soft red lipstick. Looking in the mirror, I realized that for the first time in my life I didn't mind my soft blonde curls at all. Suddenly, this very feminine feature suited me perfectly! I arranged my hair in what I thought was a pretty, feminine style.
Feeling very daring, I wrapped my bath towel around me as a girl would--covering all but the tops of my breasts and leaving most of my smooth, nude legs exposed. After listening at the bathroom door to make sure no one was in the hall, I scooted into my bedroom that way--trying to wiggle my bottom as I went. Once inside my room, I closed the door, turned on the light, looked at myself in the full-length mirror on the back of my door, assumed a sexy pose, and let my towel slip to the floor. All I had succeeded in doing was turning myself on--my rigid 5-inch cock was totally incongrous with my feminine persona! I realized I'd better relieve myself of that potential source of embarrassment by, well, relieving myself! As I masturbated, I thought about making love to Bill. I came quickly, into my free hand, and licked my hand clean. (Oh, how I wish I could have just sucked my own cock--or better yet, Bill's!)
When I was finished, I picked my tightest and shortest pajama top, put it on (leaving the button just above my breasts unbuttoned--realizing I was just totally thinking of myself as having a girl's body now), and admired my legs and breasts in the mirror. (Although I was pretty slim, I had fairly nice tits for a boy--"Thank Goodness for baby fat", I said to myself!!!) Happy that my lipstick appeared intact, I turned off my light, opened my door--just a crack, and got into bed. It was 9:30. Now the waiting began. After what seemed an eternity, I finally heard my parents come up the stairs and go into their room. (Wouldn't see them again.) I looked across the room at my clock radio--it was only 10:00! I had hoped Bill might follow quickly, but no such luck. In fact, as the house became quiet I realized that he was watching TV downstairs. My heart sank! I leaned out of bed, pushed my door closed, and felt like crying. Instead, I laid there, closed my eyes, and tried to think about my exciting afternoon.
I must have drifted off to sleep because the next thing I was aware of was someone whispering my name. I opened my eyes and gradually focused on Bill, looking gorgeous in only his pajama bottoms. I said, "What time is it?" (Kind of an odd response to the situation, but I was immediately thinking about how much time we might have to play.)
"It's a little past midnight," Bill said. "I wanted to make sure Mom and Dad were asleep and, to be honest, whether I wanted to come in. But, the more I thought about your face and your mouth this afternoon, the hornier I got." Then came the clincher: "What's your 'girl' name?"
"I'm Gail," I said, as I pulled the sheet and blanket back to reveal my legs (which I'd tried to arrange fetchingly--probably a waste of effort since it was pretty dark) and invite him to lie down with me. He sat on the edge of the bed, took off his pajama pants, and climbed in beside me, nude! Once again, just like that afternoon, I could hardly believe my good fortune! I immediately turned on my side to face him, conscious of wanting to squeeze my tits together and arrange my legs in as feminine a manner as possible. I gently, femininely caressed his cheek with my (hopefully) soft hand (not wanting to seem too overanxious to reach for his cock). I just couldn't believe that Bill had come to my bed to make love to me! I was really going to be his girl!!!
Bill put his hand behind my head and pulled me toward him. He kissed my lips softly. "I had put on lipstick for you, but it's probably gone by now. Sorry!" He kissed me again, then harder and his tongue was pressing against my lips. I had never made out with anyone before and had never even heard of French-kissing! I just knew I wanted Bill to take any part of my body he wanted, so I parted my lips, and when his tongue entered my mouth I sucked on it like I had sucked his cock that afternoon. It seemed like the natural, feminine thing to do.
"I can still taste it," he said. We continued making out for several minutes. I moved my hands behind his head and ran my fingers through his sexy hair as we kissed. I was in heaven!!!Kissing him was wonderful! He surprised me by biting on my bottom lip during some kisses, but I didn't mind. He was soooo passionate!!! Then, as we were making out feverishly, Bill unbuttoned another button on my pajama top, exposing my breasts further. I was thrilled because I thought he was going to suck my tits--just like he'd make out with a girl, but he pulled the edge of my pajama shirt off my right shoulder and began kissing and licking it. Mmmmm! Next thing I knew he was biting it--Hard!!! I was shocked, but immediately thought that now I knew what the expression "hurts so good" really meant! I opened another button to expose my left shoulder so he would know I wasn't unhappy in the least with his sexual aggression and hunger. He quickly switched to biting, kissing, and licking that shoulder, as I purred and moaned.
"Oh, Darling!" I blurted out as he devoured me. (Oh, no! I hadn't wanted to speak or do anything to break the romantic spell.) I immediately thought that I could distract him by moving my hand to his cock, as he continued biting and sucking my neck and shoulders. He was hard as a rock!!! I started to caress his erection with my hand. Bill stopped biting my shoulder, groaned, and pushed my head down under the sheets toward his cock. I slid down and kissed his cockhead. It was covered with precum, which I licked up like a kitten. Then I pumped his shaft with my hand and was rewarded with another big drop--I spread it on my lips with a quiet "Mmmmm" and took him into my mouth.
This meeting with Bill's cock was much nicer than our encounter in the park because now I could take my time pleasuring his wonderful cock! As I began to suck his velvety cock, Bill stopped pushing on my head and began caressing my hair, saying things like "Oh, Gail! Yeah, that's the spot! Oh, you make me feel so good, Baby! Never stop sucking it!"--all of which inspired me to try to please him even more! In my cramped position--jammed into the bottom of the sheets--I was able to bring my left hand up to caress his balls as I continued sucking. I focused on going all the way down on him, then slowly working my way back up while sucking hard. I kept my tongue active constantly to maximize his pleasure.
Things seemed to be going very well; Bill was groaning in a very complimentary way! But, I was feeling really cramped with my legs and feet jammed in at the bottom of the sheets, so I decided to take a chance and kind of rose to my knees--still keeping my mouth on his cock--and swung my legs and bottom around so that I could stretch out a bit more, with my feet up by Bill's head, and laid on my tummy. I licked and sucked him vigorously and Bill began to run his hands along my smooth legs, which felt divine! One thing I particularly loved was when he would run his finger up the back of my leg from my ankle to my bottom--it was like he was tracing the seam of an old-fashioned stocking. He did that several times to each leg and I purred contentedly through my full mouth.
One time that Bill's "tracing" reached my bottom, his finger continued up and began circling and pressing against my bottom opening. (This was REALLY getting interesting!) I let a little moan escape my full mouth and wiggled my bottom a bit to encourage him (feeling very happy I'd cleaned myself so well "back there" during my shower). I next felt a wet finger trying to enter me. It wasn't so bad, even when it squeezed past my sphincter, and it made me feel VERY feminine. I tried to continue focusing on sucking Bill's cock, but now I was imagining him fucking me with it someday. I thought about how I'd be a REAL woman when we reached that event! But, for now, Bill's finger moving in and out of my bottom as I sucked his cock seemed just right!!! Soon, Bill withdrew his yummy finger and I felt kind of empty--although I still had a lucious mouthful!
Then, suddenly, Bill must have stuck two fingers into me. I jumped involuntarily and squealed "Oh!" Along with this more substantial presence stretching my bottom, I also thought that he was becoming much rougher. His thrusting fingers in my pussy (and cock in my mouth) both seemed to have an increased urgency.
He said, "That's one tight pussy, Bitch! Easy to tell you've never had a man" as he rammed his fingers in and out of me. Finally, he removed his fingers, I must admit, to my relief, but after only a few seconds. it felt like his entire damp fist was invading my bottom!!! I guess it was really only three fingers, but the pain was intense. Also, the force of this new penetration seemed even rougher. Still, I didn't dare risk telling my new lover that he was hurting me. I gradually became a bit more used to the severe stretching of my insides being caused by this 3-finger phallus.
Then, Bill yanked his fingers out of my pussy, pulled his cock out of my mouth (scaring me that I might have nicked him with my teeth!), grabbed my hips, said "Come here," and flipped me around so that my head was by his, but my back was to him. He put his arms around my hips and began to spoon, jabbing his wet, erect cock toward my pussy opening. Once I realized that he wasn't angry, but wanted to play with his "girl," I felt a lot better. As his jabbing continued, I realized that Bill intended to fuck me--TONIGHT! My mind was racing--I wasn't ready for this, but I realized my actions had suggested to him that I wanted this. Realizing I couldn't chicken out now without losing Bill, I tried to calm down by reminding myself that, after all, after surviving Bill's three violent, giant fingers (complete with nails), I should be able to accomodate Bill's smooth cock. I decided I should help him and actually reached back and pulled my left "cheek" outward to give him better access to me and began to move my bottom to encourage his activities. I also took his left hand off my hip and brought it around to my breast. (If I was going through with this, I definitely wanted to be made love to like a girl!)
Bill's wet cock was actually beginning to feel quite wonderful as he rubbed around my rear opening, especially since he combined it with tweaking my nipple with his hand and kissing and nibbling my neck! Still, I wished I had lubed myself with some vaseline--I just never thought we'd get this far, this fast! The next thing I knew, Bill was trying to stick his cock through my (slightly) wet opening--"This is it," I thought!
In spite of all the preliminary stretching with his fingers, the pain was intense as his big, hard cock forced it's way through my anal ring! I asked him if he was inside me and to please take it very easy, but, instead, he became even rougher--grabbing my throat and whispering "Shut up and take it, Bitch!" I was shocked, but the funny thing was I realized my little cock was being aroused by his manly cruelty toward me. I accepted that, painful or not, this was going to happen just the way Bill wanted it to. I also remember thinking that I'd heard somewhere that women often find their first sexual experience painful--so I just told myself that this was also part of my becoming a real girl. After all, a big, strong man should be in charge and dominate his little girl! However, these distracting thoughts did little to relieve the searing pain as Bill drove his cock deeper and deeper into me. I tried to think more sexy thoughts, but it was difficult.
At least Bill seemed to be enjoying himself! He kept saying things like "Oh, you're so tight, Gail. I'm gonna turn your cunt inside out!" After a while, the pain seemed to diminish magically and I began to really enjoy Bill's thrusts! I moaned and turned my neck for brief kisses. I found that I wanted him even further in me--when it felt like he was all the way in, he was hitting some VERY pleasurable spot!
I whispered, "Oh, fuck me, Bill!!! Please fuck me deeper! I want you all the way in me!" He picked up the pace, thrusting as hard as he could each time. I said, "Bill, may I turn on my back so you can fuck me like your wife?" (I don't know why I said "wife" instead of "girl," and I felt silly when Bill gave me a puzzled look.)
Still, he pulled out and said, "Okay, move, Baby." I didn't waste any time. I rolled on my back, swung my legs up on his shoulder, and arched my back to give him full access to my wet pussy. He grabbed my hips and thrust his cock in to the hilt.
"Oh, yes, Darling!!!!" I said through clenched teeth. He rammed me over and over, my head sliding back against the headboard. Too soon, his body stiffened and I could feel him pump his seed into me. "Now I really am a girl," I thought! I felt sooo proud!!! Bill threw my legs to the side, off his shoulders, and collapsed onto me. His cock was still inside me and I hoped for a kiss. He didn't disappoint!
It's funny, but my next thought was that I couldn't let Bill's cum run out onto the sheets. Cleverly (I thought), after our kiss, I said "Let me clean you off with my mouth, Darling." Bill pulled out of my pussy and I was able to turn on my side--I hoped that turning my bottom up would keep his seed inside me. Bill presented his shrinking cock to my mouth and I proudly licked his cum, tasting him and my musty ass juice (and even a piece of my shit)--didn't bother me at all--I was a woman!!!
Bill started to harden in my mouth and I thought "Oh no, I need to clean up and get some sleep!" (I remember thinking that my post-sex thinking also seemed very feminine--focusing on practical issues.)
Fortunately, Bill must have been spent; he pulled out of my mouth and said "That was good! Good night, Gail", and went out to his room. Later, I came to resent men making such quick exits, but that first time, I was very relieved. I raced to the bathroom and let all Bill's cum run out of me, as I reflected on this life-changing day and night. Ummmm!!!! It was only then that I realized I had never even become erect as Bill made love to me. It seemed right--I was a girl, after all. I was also pleased that I had avoided Bill possibly being grossed out by encountering a manly cock other than his own. Anyway, I was sure I would always want to please men who would love me as a girl.
As you can imagine, I really didn't sleep in the few hours left that night. Too many wonderful, sexy thoughts and plans racing through my mind! And, now that Bill was gone, I came twice in my hand thinking about my incredibly sexy night!
Hope you enjoyed these stories! Thanks for reading!!!!