Chapter 10
/BB
"I just... I don't quite get it?"
"What's not to get?" Jamie said. We were sat on the sofa the day after I'd been to Toby's. He was out today so we'd both showered at his place using the spare key.
"So... they understand that it's fake, right?"
"Of course!"
"So... they like thinking that girls are morons?"
"No! Well yes, some do like that. But it's a fantasy, hun."
"A fantasy about... girls getting stuck and... raped?" Jamie squirmed a little.
"Nooooo, not exactly" Jamie began. "It's... look, a lot of guys -- and some girls -- like the idea of a woman who's-"
"Stuck in a washing machine?" I filled in and Jamie gave a big sigh and shook her head.
"Look, it's just like people who tie each other up or cuff their partner to the bed. It's about control, not Ra*e. It's fine as long as everyone agrees to it."
"I don't really get that." I said earnestly.
"That's fine, hun. It's not my thing either." I didn't say it wasn't my thing I thought, I said I didn't get it.
"Have you tried?"
"Yeah." Jamie said and I felt my heart sink a little -- even now, sometimes I felt like such a dork compared to her, she was so much more experienced than me. I let the matter drop.
"Well" Jamie said after a little while. "why don't you ask Toby about it next time you're over and... entertaining him." She gave a wicked grin and I blushed.
"I- that was just a spur-of-the-moment thing, I'm not sure it will ever happen again."
"Okay, hun."
"I mean it."
"Okay, hun. I'm sure you'll never suck Toby's dick again."
The next day, I was leant over Toby's crotch, my lips firmly wrapped around his dick as he lay in bed and groaned in pleasure.
I swear I hadn't planned on it! It just... sort of happened. I could tell from the moment I walked through the door he was a little different; nervous but he was also jittery -- excited, expecting. I didn't want to disappoint.
"Ngggh! Ooooooooh fuck!" Toby groaned and writhed underneath me as I kept working his cock with my lips and tongue. At least with Toby, I knew I was the experienced one. He bucked and I pushed myself down, again burying my nose in his pubes and took his entire cock in my mouth as he came -- I allowed his semen to fill my mouth and down my throat without letting go -- and this time I was ready for the huge amount of cum he produced. I didn't let a drop go to waste. Finally, I slowly eased off his dick until my lips were wrapped around his head and with a gentle 'pop' I separated from him. Toby's breath was ragged; poor boy was spent and I wiped my lips with satisfaction.
"They say they're gonna fix the water this afternoon." I said a few minutes later once Toby had put his trousers back on and we were both sat on his bed.
"Oh." he managed, obviously a little disappointed.
"Thank you so much for letting us use your place."
"Of course, any time." He said, not really looking me in the eye. Feeling a little blue, I got up and went to gather my things from the bathroom. I slipped into my shoes and had my hand on the door when Toby emerged from the bedroom.
"Wait!" he said and I turned around. He didn't say anything for a little while but then finally asked me: "Would you..." he began, still struggling. "Do you want to go on a date with me?"
That wasn't something I had expected. I froze for a moment, my hand still on the door.
"You... I mean... we..." I took a moment to gather myself. "You don't have to, I mean you don't owe me -- or I mean, we don't-" I struggled, feeling very embarrassed, awkward and not a little confused. How did this happen? A few minutes ago I had felt so in control, so confident and now I felt like a shy high school girl. Again. Dammit, I didn't want it to be this way. Was he trying to bribe me? Was he trying to keep a good thing going? Had I been stupid? Was Toby not the guy I thought he was?
"I like you." Toby said and I snapped back into reality. He looked nervous; more nervous than usual. "I... I really like you. And not, not for... you know." He made a vague gesture towards the bedroom. "You're... fun. You're easy to talk to. I like you. And I would like to go on a date with you."
"Like a 'date' date?"
"Yeah. I... know a place. I mean I've never been but I've been told it's nice." My head spun.
Don't hurt him. a voice in my head said. Whatever you do, don't hurt him. But hurt him how? By saying no, well sure. Or by stringing him along. I'd sucked his dick twice, I felt pretty sure that was the kind of thing that made guys think you were into them.
But wasn't I? Yeah, I kinda was. Had I really given him blowjobs as a... what, a favour? A way to repay him? Or just to make myself feel good?
No, I hadn't. Toby liked me, or at least he said he did. And I liked him. He was nice, sweet and shy. He didn't just make me feel experienced and bold, he made me feel safe and wanted. And he wanted to go on a date with me.
"Okay." I finally said. "Erm... when were you thinking?"
"This Friday?" Toby said, his eyes lighting up. I smiled.
"It's a date. See you then."
Thursday evening that week I lay in bed, thinking. I'd picked out what to wear; a knee-length skirt and my nicest top -- nothing too fancy, but nice. I'd told Jamie it wasn't a big deal and I didn't want her help picking an outfit, then earlier today I had realized I was nervous as heck and begged her to help me pick out an outfit. She'd assured me what I'd picked was fine. She'd also several times assured me she was fine with me going on a date, just like she was fine with me screwing around with Toby (her words). She'd told me was that as long as I didn't hide anything from her, she was fine. But she had told me to be careful -- Toby seemed a sensitive sort and she didn't want either of us to get hurt. I loved her so much. I still do.
I was nervous. Really nervous. Like butterflies-in-my-stomach nervous. I kept telling myself I was being silly. You've sucked his dick for god's sakes -- he's seen you naked and watched you masturbate.
But he was sweet and when he had told me he liked me I can honestly say it slightly made me knees buckle. Mark was handsome enough and when we were first started dating he seemed nice but he was never sweet. I knew Trevor well enough by now to know he wasn't interested in me or Jamie, romantically -- we were friends who occasionally had sex on camera for money, but that was it.
Hank... Hank did say he liked me and he seemed like a really nice guy. But Toby was different. If he liked me that felt special. Like something I thought I'd lost. Innocence, maybe?
I couldn't stop thinking about it. So I decided to do something else to take my mind off things. I decided to work on my side-project for the last week or so: I was going to keep practicing having anal sex.
My toys had shown up about two weeks prior and as soon as they got here I had opened the box, taken a look inside, gotten scared and shoved it under my bed and pretended it wasn't there. Then, a few days later I had taken my first tentative steps.
I'd read a lot of tips online and, again, had gotten scared and decided it wasn't for me. Then I'd changed my mind. I wanted to try. Part of it was because Jamie had said it wasn't something she'd ever done.
It had been a little bit of a surprise to me when she told me. It was just after I ordered the box of stuff, which I'd told her I was thinking of when she admitted it wasn't something she'd ever really gotten into.
"Don't get me wrong -- I've had guys try -- only guys, mind you. Once I even let someone slip a finger in there, to try. But it wasn't much fun, let's just leave it at that."
So in other words, here was something else that I could maybe do that she wasn't experienced in. That, and the memory of Trevor guiding his cock over my asshole sealed the deal for me and I had gotten into it.
I lay down on the bed on my back, lube at the ready. I still wasn't great at estimating how much to use but rather too much than too little, I figured. I played with my pussy for a short while, just to get in the mood. Eventually my fingers moved further down between my legs and I pressed gently on my hole. My body remembered Trevor doing it and I felt myself tense. A deep breath and I willed myself to relax. I applied a gentle pressure and the tip of my finger started sliding in.
It felt so different that having something in my pussy -- definitely a lot scarier but mostly just very different. The first time I hadn't been sure what to expect but now I was more prepared. I applied a dob of lube to my finger and this time it slid in further, I felt my sphincter tighten around it almost reflexively and had to will myself to relax, not tense up -- I'd learned that quickly.
I lay there still, fingertip in my ass, breathing for maybe a minute before I slowly pulled it out. At my bedside table lay a silicone dildo; modest, but with a flared base (very important tip I'd read online). That was important. It was only my third time using it and I wasn't planning on going much further than last time; slow and steady wins the race, I thought.
I moved the dildo down between my legs, plenty lubed up -- stupidly I'd forgotten to put a towel down but it was too late -- I'd have to change bed clothes when I was done. Gently bracing the tip against my ass I took another deep breath. I pushed it in -- very, very slowly. I knew it was going to seem like it couldn't possibly fit and I knew how scary it would be the first moment it went in -- for a moment it would feel like it was going to get sucked in and get stuck. That had been another moment where I very nearly abandoned the whole idea. But now I was ready for it. It had a ridged 'head' and I slowly, slowly pushed -- gentle pressure and then it went in.
Just like my finger it was just the tip and it was only a little thicker but it was in me. I gasped but focused on not tensing. Tensing didn't hurt, exactly but it made it less comfortable. I had a good inch of it inside me, I knew. It felt good, mostly because I felt a sense of pride; of accomplishment. I moved my other hand to my pussy and started rubbing my clit. The combined feeling made me tremble in pleasure -- I felt stuffed. I started moving the dildo just the tiniest bit, a tiny bit further in then slowly back out.
I'm fucking my own ass I thought to myself with a real sense of shameless pride. Rhythmically, I fingered myself and moved the dildo. My mind wandered. I thought of Trevor and his big, massive cock. Then of Toby and I paused, my head suddenly full of new fantasies. Toby's cock was shorter than Trevor's but much thicker. Would I ever be able to handle something that big in there? I wondered but almost as I thought it I willed myself to push the dildo in a little deeper -- deeper than I had ever done before. Still only barely an inch and a half, but still. I thought of Toby's fat cock filling me up. Then of Trevor's long, beautiful, dark cock. Spoilt for choice. At least, in my head I was.
Minutes passed and all the time it felt easier and easier -- plus I was getting closer. As I felt myself nearly there I gave the dildo one last, slow but deep push. It was only six or so inches long and I'm not sure how much of it I got inside me -- it can't possible have been even half but that night it felt like the whole thing. I filled my own ass and came, thinking of Trevor and Toby taking turns deep inside my tight, virgin butthole.
I fell asleep without changing the bedsheets and woke up the next day a little sore, but happy, proud and a little less nervous for my date.