The Switch Up Ch. 04

"Yeah, in that draw," I said, nodding to the bedside table by her side. She reached over and opened it, once she had finished undoing the rope around my legs, and pulled one out as I got completely naked. She followed suit, and finally I was able to see her in all her glory; words would not even begin to describe just how incredible she looked, she was as close to perfection as you could get. I could not believe I was about to have sex with this girl, never mind effectively lose my virginity to her.

Emma ripped the packet open, and ensured the condom was facing the correct way before balancing it precariously on the tip of my cock. She turned, and began to kiss me. The kiss was one of the more intense ones I have had, even in my own body, and as it was going on Emma gently unrolled the condom onto my cock with one hand. It was tight, but not too noticeable, though I could see why guys chanced their luck so often in an attempt to not use one. I sat up to allow myself to get on top, but she pushed me down and straddled her waist.

"I still feel like I owe you for that pussy eating, so you just sit there and relax," Emma told me, which caused me to be slightly disappointed as I was looking forward to thrusting into a woman for the first time; it was also a blessing in disguise, as I was worried I would not live up to Dylan's reputation and this way all I had to do was lay there. She shifted her weight forward slightly so my cock was in perfect alignment with her pussy. Knowing the trouble with this move myself, I grabbed the base of my shaft and held it steady as she slid down. The feeling of having a pussy encasing my cock was very different to her lips and mouth. This was more intense, with every area of my cock a source of pleasure. The pressure and the warm, wet walls of Emma's pussy added to the sensation. She continued to very slowly lower herself down, pausing every few seconds to adjust to my cock filling her; when she did pause she would move back up slightly, increasing the already building pressure.

Emma lowered herself all the way down, so that she was effectively sat on my thighs. She looked me deep in the eyes, and I looked back while grabbing a tit. I rubbed the nipple between my thumb and forefinger, just as Emma began her ascent. She continued moving up and down, to the pace of a church bell sounding, for a minute or two; building me up, but not enough for me to make use of the condom. Gradually she began to pick up her speed, and I helped her stay straight by grabbing her ass so I could guide her up and down my cock. The muscles in her pussy's walls really added something to the feeling.

Suddenly, my orgasm crept up on me and I pulled out on an upward movement in an attempt to prolong the session. My condom slipped off slightly, but I managed to pull it back down before it came off entirely. Emma opened her mouth in attempts for an explanation, but I just rolled her on to her back and took her top lip between mine before she could speak. Our tongues danced as my hand crept towards her pussy, and I inserted two fingers to keep her going while I took a needed break. I was glad I was experienced in how guys fuck, because if not I would have cum by now; I felt sorry for virgin boys, they would have a hard time satisfying any woman on their first attempt. Intermittently, I put my thumb on her clitoris, which caused her to physically writhe about with pleasure; this was something I had never been able to do in my own body with smaller hands, but Dylan's were perfectly sized. I kissed her neck, and that was enough for her to moan audibly for the first time.

"I'm close, finish me off with your cock. Fuck me!" she pleaded. I did as I was asked, but I was the one in control now; with my cock lined up, I thrust into her. Unused to having a cock, and indeed using it, I pushed in too hard. I realised immediately. She groaned loudly, and threw her head back as her acrylic nails clawed at my back. Her pussy contracted so much that I thought my cock was going to snap in half.

"Shit, I'm sorry!" I said, quickly trying to pull out.

"For what? Do it again! Harder and quicker! Dominate me!" she screamed, in a total U-turn on earlier, as she grabbed my ass before I was all the way out and thrust my cock back inside her like she would a dildo, to another deep groan.

I pulled back again, but this time I had no intention of releasing her. I looked at her properly for the first time, and realised just how much she turned me on; not just that she was hot, but actually having some feelings towards her rather than looking at her as a sex toy for my pleasure. I thrust back in again, a little lighter than before, but this time I picked up the pace trying to find a rhythm. In a similar way to cutting wood with a saw, I slowly found my groove, and increased my pace with each stroke. Her moans turned into cries, and her cries into screams as my own orgasm neared once more.

"I'm cum-cum-cumming!" she screamed, digging her nails into my back as I relentlessly kept up the pace, the adrenalin pumping through my body masked the pain. "Don't stop!"

"Me too!" I shouted, trying to hold off until Emma came. There was nothing worse than a guy cumming and deciding to stop when were right on the edge. The pressure was really building, and I tensed to hold off my inevitable ejaculation like I would to stop myself peeing.

"Yes! Yes, yes! That's it! Ahhh!" Emma cried, her pussy convulsing around my cock, which proved to be too much for me. The build-up of my orgasm had become too powerful, and overpowered my attempts to stop it. Instinctively, I leaned down and kissed Emma our lips meeting just as I felt myself cum, as her own orgasm tailed off. Despite only cumming fifteen or twenty minutes ago, I pumped at least five more times and what I imagined were healthy sized strings of cum out. Finally done, I collapsed on top of her, forgetting my new size.

"Shit, Dylan," she groaned, trying to push me off of her.

"Sorry," I said, pushing myself up slightly after working out she was talking to me.

"Are you going to pull out, or are you leaving your cock in my pussy forever?" she teased.

"Sorry," I repeated, forgetting that I was now the one that had to pull out. I rolled off her, and grabbed a tissue which I used to pull my condom off with before chucking it in the trash. Emma gave me a gentle peck on the lips as I lay next to her.

"Stop apologising, I think that was the best sex I've ever had," she blushed. "And I didn't even have to tell you what to do, it was like you knew where every spot was. You must have had sex hundreds of times!"

"I don't know about that," I murmured, trying to play it off.

"Well I do," she smiled, kissing me again. "I'm glad you finally stopped fucking that good-two-shoes long enough for us to do this."

"Which goody-two-shoes?" I asked, not seeming to recall Dylan telling me about this.

"Mollie?" Emma replied, confused as to why I did not know.

"Oh her!" I said, trying to hide my shock; Dylan definitely did not tell me about this.

"Yeah, I'm glad you turned her down when she wanted to make it official, otherwise I would not have felt your massive cock ripping me in half!" she giggled, as I tried to comprehend what she was saying.

"You okay, Dylan?" Emma asked, concerned as she traced my abs with her finger.

"Erm, yeah sure, I'm just glad you enjoyed it," I said, realising I had spaced out a bit thinking about my brother and best friend fucking. How did I not realise?

"Enjoyed? More like enjoying, we're not done yet!" she whispered into my ear, which caused my cock to stir even more than it had from just thinking about Dylan and Mollie, despite its previous work.

"I think I might be," I said, still breathing a little heavily; it was not often I got to experience two orgasms in a single session, along with all the action usually required as the man rather than the woman.

"I think someone disagrees," Emma giggled, noticing my semi and grabbing it in her hand which only caused it to get bigger. "And I want that someone to go where no one has ever been before."

"And where would that be?" I asked quizzically, not getting the hint once more as she stood and swayed her way sensually towards the bathroom; I tended to be the one saying sexy things like that and dirty talking, so I was not used to reading signals.

"Bring some lube," she said without turning to look at me, and spanking the area of her body that contained the only hole my new body had not yet explored. Now realising what she was suggesting I moved faster than I had ever done previously in my life, scrambling to find some lube and scampering after her into the bathroom. I loved ass play as it was, and was a master with a strap on, so the idea of doing the same thing and getting pleasure from it really turned me on. Emma was already under the shower, and as I stared at her heavenly body time seemed to slow. She told me to run the bath, and I did as she said before joining her under the water.

"Is that uncomfortable?" she whispered, nodding at my crotch as I joined her in the shower; at first I thought she meant my almost erection, before realising she was talking about my overgrown pubes.

"Not really, well, a little itchy I guess," I answered honestly.

"Well, I'm sorry I put you through that," Emma apologised, moving in and kissing me as the water ran between our lips.

"It was more than worth it for this," I whispered, sliding a finger into her still sticky pussy.

"I can't argue with that," she giggled, as she leant back and trusted me to keep her upright, as water bounced off her tits. "But let me sort that for you."

"Okay," I agreed, with no thought required; I had Emma Charles, one of the sexiest girls I had ever fucked in front of me- she could tell me to jump off a cliff and I would. Maybe I was really turning into a guy.

She skipped out of the shower and back into Dylan's bedroom, "Sorry to get your floor wet."

The implement Emma came back with struck fear into me; it was a straight razor, the kind a barber would use to shave a man's face. I did not like to even shave my own legs with my Venus, so I certainly did not want to have someone set to my bush with a naked blade. She fumbled around behind me, and grabbed a can of shaving foam. As she gently squeezed some into her hand she leaned forward, taking my semi-hard erection into her mouth. Emma gently sucked on my head, preparing me for round three, as she began lathering up my pubes. Three was the record for the number of times I had done it with a guy, but it had taken us all day.

"Why did you ask me to grow it like this?" I asked, intrigued.

"Well I usually use it as a control tool when I am fucking guys, and sometimes there are tweezers and a little hot wax involved," she said, pausing, evidently remembering past experiences. "But like I said before there is something different about you, I just can't put my finger on it. You're not the usual dumb as guy just pounding away until you get your fill. I trust you to satisfy me."

Without any more words, she opened the razor and it was I who had to trust her. She made her first, swift movement and a clump of pubes swirled down the drain. It took her less than two minutes before all of my pubic hair, well my brother's, was gone. I knew he usually liked it short anyway, so I was sure he would not mind too much. She returned her attention to my cock, giving me nothing short of a blowjob to ensure I was hard again. Satisfied, she stood wordlessly and sashayed over to the now full bath. Emma turned the water off, and then bent over giving me a brilliant view of her ass. It was more than clear what she wanted me to do. I followed her into the bath, if it could be described as that; it was part bath and part hot tub, and with its size could be part pool. I pressed a button on the small tablet built into the bath, that could change things like lighting and control bubbles. Dylan had added these particular settings years ago, under the heading of 'Sexy Time'. The lights were dimmed, music played softly and the bubbles were on a medium setting.

"What are you doing?" Emma asked.

"Setting the mood a little," I whispered sexily.

"Change it back, I don't want this to be romantic," she told me.

"Then how do you want it to be?" I asked.

"I want you to tear me a new one," she laughed.

"Really, but you've never done anal before? You might want me to go a little softer than that," I warned, knowing from experience how painful your first anal experience could be.

"No, not properly anyway, and okay a little softer, but I'm always used to dominating someone and I want to be the one not in control for once."

"Well, I'm your girl!"

"Sorry?"

"I mean guy!" I said trying to laugh it off. "Give me a second, I'll just go and get a condom, you know because I'm a guy and I have a cock."

"Why? You're sticking it in my ass, not my pussy," she said, confused. "It's not like you're going to get me pregnant, and I've just cleaned my ass if that is what you're worried about. Now grab the lube, and don't use it sparingly."

"Why do you even want to do this?"

"Because I have never really done it before, but have always wanted to and trust you to do it. It's also where I feel the most vulnerable so it helps me get away from constantly dominating every sexual encounter I have," she said. "Anyway, I heard you were an ass man, so I thought I'd give you a treat."

"Oh, he's definitely a tits man!" I laughed, before realising my mistake again.

"He?"

"Erm yeah, my cock," I recovered poorly, before I lubed my cock up and her asshole, too, taking care to not use the right amount. I lined up my cock as I had a hundred times before, well obviously not with an actual cock but rather one of my plethora of strap ons. All of the girls absolutely loved it when I fucked them with one of these, especially Eva, it was my speciality. So I figured one physically attached to me would not be too different, and I would get some pleasure myself from it for once which would be a welcome bonus.

Emma was braced against the wall, bent over with her ass sticking out of the water which came up to her knees; she was right to do so, and I knew from experience. Every guy I had ever let do me in the ass had unceremoniously shoved half their length in, too excited that they were actually going to have anal sex to think about me. The ass is not especially designed to be fucked, its narrow, not as pliable as a pussy and certainly not as wet.

"Hey," I soothed, stroking Emma's hair. "Don't look so scared, relax a little, I'll go easy."

"Okay," she said, as she became a little less tense and her grimace faded. "I trust you, Dylan."

"It's going to hurt a little to begin, but ju-," I tried to say, before Emma cut me off.

"I trust you Dylan," she said quietly. "And I have never said that to anyone and actually meant it, let alone a guy who is about to stick his cock in my ass.

"Well, I'm honoured," I replied, realising just how fucked up this girl was. Without another word, I double checked I was lined up properly and eased myself into her. Her sphincter relaxed as my head probed, and I pushed inside but stopped once the glands of my new cock had passed.

After giving her a moment to recover, I continued, penetrating deeper. As I got halfway in, she contracted and I stopped. I bent over and kissed her back, before reaching around to find her clit; as soon as I did, she released a gasp and I restarted my forward assault on her bowel, which she barely noticed as she was too distracted by my playing with her clit.

With my pelvis now touching her ass, I was close enough to pull her head around and give her a deep kiss. This was by far the most tender, even romantic, moment we had shared all day. It was clear she had never let her defences down so much, or perhaps at all, with anyone before; she was completely at my mercy, I could ravage her whenever I wanted and not in a good way. As I stood there, slightly uncomfortable due to the position in which we were making out, I realised in a backwards way this was the closest I had ever come to making love; a disappointing realisation considering I was doing a girl I did not really know in the ass, using my brother's body. I had only ever fucked, I had never had a serious boyfriend, never felt true love, but this was different; of course, we were not in love, but we certainly did have a connection. The trust she was placing in me, was as satisfying as the actual sex. It felt dishonest that she thought I was Dylan, rather than myself.

"I have never felt so filled, so satisfied," she breathed, out of breath from the making out, our foreheads pressed together. "And that's not just because of your very large and satisfying cock."

"I feel exactly the same way."

"Would you make love to me now, not fuck me like I asked before?" she asked, a naivety creeping into her voice. "No one has ever made love to me, only fucked me...and sometimes not quite when I wanted them too."

"Emma were you rap-."

"That's a story for another time," she said, putting the issue to bed for now. "Please, just do as I ask."

So, I did. My cock was remarkably still as hard as it was when it initially embedded itself deep into Emma's ass, and I pulled out slowly before gently pushing my way back in again. I did this a few more times, getting her used to the feeling, before I began to find a slow and steady rhythm. The sensation of anal was different from being in her pussy, and in my opinion not quite as pleasurable, but it was certainly enjoyable. As I adjusted my angle, I saw a tear roll down her cheek.

"Are you okay?" I said, beginning to pull out slowly. "Does it hurt too much? Do you want me to stop?"

"No!" she urged, grabbing my cock and shuffling backwards so I re-entered her fully. "Just this is the way I had imagined my first time, a caring man who knew what he was doing, but I didn't quite get that. Please, don't let me kill the mood, carry on."

She was right, the mood had turned somewhat sombre so I decided to give her the best pick me up I could right now, the most satisfying orgasm of her life, using every trick that had ever been used on me. I restarted, and picked up my pace a little which elicited groans from my partner. She braced herself more firmly against the wall, as the water sloshed about around us. My right hand abandoned its post on her right hip, and went in search of hidden treasure. I twiddled my index finger on her clit, in the same way Dylan would do whilst playing his video games. My other hand groped one of her massive boobs, and I rubbed her nipple between my thumb and forefinger.

"Keep going, I love this! You feel so good inside me!"

That caused me to pick up my intensity. The girls had said the same type of things to me when I was pounding in and out of them with my strap on, but it had never had much effect on me; now, with 'my own' flesh and blood violating this girl's ass, her words seemed to really appeal to my newly discovered male ego. Something that did not make too much sense, if you consider the fact that my brain appeared relatively unaltered.

Emma's moans increased, and she herself began pushing herself back against me with each thrust as if she was begging me to go deeper. The fortunate thing about having already cum twice today, is that I could keep up this rhythmic pounding for longer than before which really allowed me to build Emma's orgasm. After a few more minutes of thrusting, moaning and the occasional kiss or grope I was close.

"Jesus Christ, Dylan, you've got me close to orgasm just by fucking my ass," she said breathily.

"And a little bit of clit play," I warned. "I'm close though!"

"Oh, please -ah- wait for me," she pleaded, through pleasurable sighs. "Fuck me harder; a little quicker and I'll be nearly there."