How I Met My Husbandbyjessymichelle©
Tim was a cute boy in a nerdy kind of way. Beautiful smile, though. He was about 5'9, dirty blond, skinny, kind of dorky, kind of messy, but a good guy and a better friend. I was only a bit shorter than him, but even skinnier, leaner, and tan from every morning I spent swimming for an hour.
Being both college freshmen when we first met, we helped each other through classes, homework, jobs, and girls. And after 2 years, we were pretty close friends, so I suppose it was only a matter of time before he found out about me and my not so little secret.
"Uh, hi," Tim said. He looked at me with his jaw agape, as if he was trying to say something but couldn't form the words.
"Oh. Um, hey. I didn't think you'd be back so soon," I said sheepishly.
"Class got canceled. Josh, what's going on?"
"Um, well, I like to dress up sometimes."
"Oh," he said. "I'm just gonna step out for a second and let you-"
"Yeah, thanks," I said as he closed the door.
I was scared out of my mind. How could I have been so stupid, so careless? My heart was pounding as I changed back into my guy clothes. Then I heard him knock at the door.
"Can I come in?"
We both sat on the couch in silence. I couldn't look at him, but I could feel his eyes on me. I felt like dying, instead I started to cry.
"What's wrong?" he said, I could hear the concern in his voice.
"Oh my god. I can't believe this. I really can't," I said, humiliated beyond belief. "You're like the last person in the world I would want to know about this." In my haste I had neglected to take off my eyeliner and some of my makeup and it was running down my face.
"Its..it's okay. I mean, it's not like you're doing lines of coke or anything. Are you?" he said jokingly, trying like always to make me smile.
"Heh, no," I said. It had worked. I looked up at him and he wasn't looking at me like I was a freak. He scooted closer to me and handed me a tissue.
"Thanks," I said, blushing a bit. I still wasn't quite comfortable with the way he was looking at me.
"How long have you been doing this?"
"Since I was young, like 10 or 11. I've managed to keep it a secret until now."
"Wow," said Tim. "No wonder you looked so good."
"Shut up," I said as I playfully punched him in the shoulder. We were both smiling now.
"Do you have a name?"
"I go by Jess. Like Jessica."
"Didn't you have an ex in high school named Jessica?"
"Yeah, but I just liked the name. Plus there was this one time I asked my mom what my name would've been if I was born a girl, and she said she was betwene Jeanette and Jessica because she likes names starting with the letter J."
"Right," said Tim. We sat there, and the awkwardness was starting to creep back. It reminded me of the handful of dates I had been on, where I would run out of questions or witty comments to say to a girl, and we'd just sorta sit there in silence. But then Tim asked the inevitable.
"So are you gay?"
"What? No! I'm still attracted to girls, dude."
"Just asking. I mean, it's okay of you are. I just wasn't sure if I had been rooming with someone for the last 2 years who's been checking me out when I'm naked."
"You are such a guy," I said, smiling again.
"So? I was checking you out a minute ago."
"It actually took me a second to figure out who you were," he said as he scooted even closer. "At first I thought that maybe you'd finally invited a girl up to our room, but then I recognized the birthmark on your arm and then your voice"
I sat there, flattered but kind of embarrassed, with absolutely nothing to say, until…
"You look pretty good as a girl," said Tim. "I think you could totally pass as a chick."
"Yeah, except this isn't a co-ed dorm. I think someone would notice that Josh disappeared and some new girl who kinda looks like him is living with his best friend."
"We're best friends?" he said.
"Duh." I leaned over and hugged him. It felt nice, but different. Of course we'd hugged before, like at New Years and at games and stuff, but I felt like I was there with him at that moment as Jessica, not Joshua. And then, I acted on impulse and did something I probably shouldn't have: I kissed him on the cheek.
We both pulled away suddenly and just looked at each other. Something was going on.
"Can…can I see you dress up again?"
"Okay," I said as I turned and walked into my room. I kept telling myself that I wasn't gay, that I wasn't attracted to guys. I threw on a pleated skirt and a cute t-shirt, and fixed my makeup and breast forms. Part of me felt like it was all wrong, but right now, I wanted him to see me, to really see me. I just wanted to look beautiful for him.
"Wow," he said as I sat next to him again and crossed my legs. "Perfume?"
"I'm not wearing any, genius."
"I guess I just like the way you smell."
I shoved him. What a dork.
"You've been using that line, since, like, ever, man," I said. "But it was kinda cute."
"You're kinda cute," said Tim. He brushed my hair out of my face. His hand was now on my cheek.
"Hey, are you flirting with m-" I asked. He pulled me towards him and kissed me. I had never kissed a boy before, and I was completely lost in the moment. My head was swimming. My knees felt weak. I noticed his surprisingly soft lips first, then his aftershave. His tongue then slipped inside my mouth, and I began to lick it and suck it the way girls in the past had done with mine.
"You even kiss like a girl," he said as we both took a deep breath. I took the opportunity to straddle him and throw my arms around his neck. I always loved it when a girl climbed on top of me and took control. So I began grinding myself into his crotch as we made out, and I felt his hands move from my face to my hips.
"Do I turn you on, Tim?"
"Aah," was all he could muster as I sucked on his lower lip.
"Am I getting you hard?" I asked while kissing him. I knew the answer, I was grinding my crotch into it, after all. But I wanted to hear him say it. I moaned into his mouth every time I brushed my tits against his chest. They were fake, but it still felt extraordinary. And I could tell it was driving him wild, the way I was pouring my whole body into his lap. My hands left his neck and reached for his pants, but I could already tell what his body wanted from me.
"Want me to go down on you?" I asked in the most girlish way, hoping he wouldn't say no.
"Yes," said Tim so weakly. I kissed down his neck, took off his shirt and kissed my way down his chest, stopping only to kiss his nipples, until I made my way to his stomach. I undid his belt buckle and pulled off his jeans. Then he took off his boxers, and for the first time I had a real cock in front of my face.
I took hold of it in my hand and began stroking it. It felt so right, so much like mine, only bigger, thicker. I started licking up and down his shaft, sucking on his balls, and pulling down on them as I finally took the head of his cock in my mouth. His hands were on the back of my head. He was pulling on my hair a bit, and I liked it. I took it out of my mouth for a second and started licking the tip like a lollipop. A string of saliva and pre-cum went from his wet cock to my lips. Looking up at his eyes, and I gave him a wink. I continued sucking on him, enjoying the scent of his manhood, and he began gently thrusting himself, trying to make love to my mouth. He looked so vulnerable right now.
"Tell me when," I said.
I never wanted anything more in my life. This feeling, of him using me to get off, and feeling so sexually desired, is this how girls feel when they do this?
"Oh, god!" he moaned. He was pulling my hair pretty hard now.
And then it happened. He came in my mouth. I felt every spasm of his cock as he began filling me. I didn't think about whether to spit or swallow; I let it all down my throat. It was so warm, salty, thick, but it wasn't bad. I loved being so lost in him.
I sat up, wiped some of his cum off my lips, licked my fingers, and teasingly gave him a quick peck on the lips. He sat there, completely gone.
"Can I return the favor?" he asked.
"I want you to," I said. "But, it's just that, I've never cum before. Like, every time I've been with a girl, whether she was going down on me or when we had sex, I've just never had an orgasm except when I'm by myself. It didn't feel right, the way I was doing it, sticking myself into them. The only time I really enjoyed it at all was when they were on top, and even then, just picturing my cock going inside them was a turn off for me."
"Say no more," said Tim. He started kissing my neck, then nibbling, harder and harder. He kissed my tits, and told me to take off my clothes.
"Can I leave my bra on?"
"Whatever you want."
I took off my shirt, and slipped off my skirt. I had a noticeable bulge in my panties, boy shorts, ironically, which he pulled down to my ankles. He started kissing my cock, and then he started rubbing it.
"Don't," I said, holding his hand away from my crotch. "It makes me feel like a boy."
"But you're not," Tim said. "You're a beautiful girl, Jess."
He started licking at it as I laid down on my back, knees up, and I kicked off my underwear. He kissed the inside of my thighs, then he began licking only at the pink tip of my cock the way, I imagine, he had licked other girls' clits.
"Oh, god!" I moaned loudly, as the feeling was too intense and my passion escaped my lips. "Call me Jess again!" I was breathing pretty hard. I had one hand inside my bra massaging myself and one hand on his cheek.
"I want you, Jessica."
"Tim, I...I want you. I want you inside me so bad. Will you...will you make me a woman? Will you make love to me?"
"Turn over," he said. Now I was the vulnerable one, on all fours and on the floor. I could actually see myself in the reflection of my full length mirror. I looked like a girl who was about to get taken from behind by her well-hung boyfriend. Instead, however, I felt his lips again. He was kissing down my back, to my bottom, where I then felt his naughty little tongue again.
"I wanna eat you out," he whispered. That wrong feeling came back for a second, like a part of my boy mind was fighting me with everything he had. But it was drowned out by the sounds I was making. I was succumbing to the lust inside me. It felt amazing, his warm breath against my hole, then licking me, wetting me with his tongue, over and over. It was the closest I'd come to having an orgasm with another person.
"I think I'm ready now," I said softly.
Tim was on his knees, and he positioned his himself behind me. I felt his hands grab my hips, but then they left. I heard him reach for something in a drawer. And then I felt 2 slick fingers run across my ass, and one slipped inside me.
"Whoops," he said, always playing around. He was fingering me gently, working me around, getting me ready for him.
"Since when do you have KY?" I asked him with a bit of a surprise and quite a bit of lust.
"For special occasions," he said with a grin.
"So's this, big boy," I said as I took out a condom from the bottom drawer and put it on him. Spermicidal, ironically, which we both smirked at. I had only put a condom on my own cock once before. But doing it for someone else was much easier, though, especially after his cock was wet with pre-cum and saliva. It was really turning me on as my hand slid over his uncut manhood, which seemed to only get bigger and bigger.
I could feel the heat coming from his hard cock again. Then I felt his tip touch me, and slowly I felt it, inch by inch, enter me, until what felt like all 7 inches of it was inside me. I could feel his balls against my ass. He then pulled it almost all the way out, until I only felt his head again, and then he thrust deeply into me again. It hurt, but it felt so unbelievably good.
"Pull my hair," I moaned, really loud this time.
He was making a fist in my hair as he was riding my ass, pumping me. My breast forms bounced with every deep thrust.
"Harder, deeper," I begged. "Spank me."
He did. My hand moved over my cock.
"Let me," he offered. He stroked in sync with his thrusts, and I had this image of what it would be like if I had a real pussy, if I was a real girl. But in the heat of the moment, I was a real girl. I was his girl.
"Tell me how pretty I am. Am I tight enough for you?"
"You're so pretty baby. Your pussy feels so good, you're so tight. Oh god, you're so wet."
"Tim," I said, taking a momentary break from my deflowering. "I want you to take me. I want you to take my cherry on my back. I want you on top."
I laid down, and he placed a pillow from the couch underneath me, then he spread my legs and threw them onto his shoulders as I guided his cock inside me with my hand. We weren't making love anymore. I wrapped my long legs around Tim's body, and he pinned me down by my wrists, over my head. I was submitting all of myself to him.
"I don't think I can cum without rubbing it," I admitted. He let one hand go free, and I began stroking myself. I knew I wasn't going to last much longer, and neither was Tim. He was thrusting so hard, so quickly, so violently. His moaning became as loud as mine, and he let out a final, guttural moan as he finished inside me. Feeling his cock spasm, mind began to as well. But it was different somehow. It was so much more intense, like it was happening all over my body, my neck, my nipples, my thighs, my boyhood, even. I trembled with ecstasy as I finished on my stomach, and a little bit on Tim's.
As soon as he laid down exhausted, I lowered myself to him once more, cleaning my love off of his stomach and his soft cock with my mouth. We made out, tasting one another again. I nibbled on his ear, sticking my tongue in it.
"You're bad," I whispered. But he was spent. I stroked his chest and his stomach for a little while, before curling up in my guy's arms. For the first time in my life I felt safe, whole. And just before drifting off to sleep, I wondered if this was how all women felt after their first time...