“Yeah, I’ve heard that before,” I stalled.
But Dawn wasn’t letting it drop. “C’mon, Ben. How many?”
“Well I’m not going to tell you NOW.”
“Why not? Are you embarrassed the number is too low?”
Ooh, a blow to my male ego. Automatically, I defended myself by blurting, “Of course not. I’ve had three.”
“Okay, three girlfriends. I can handle that,” Dawn nodded. “Now… how many other girls did you sleep with?”
I winced and looked away. Belatedly, I tried to stammer, “And, uh, why would I sleep with anyone who wasn’t my girlfriend?”
“You HAVE, haven’t you?” Dawn’s eyebrows went up with only mild surprise. “How many others? One? Two?”
My grimace became worse.
“No way. Three girlfriends plus others… Ben, you really get around, don’t you?” Dawn chuckled.
Sensing that she wouldn’t press TOO hard, I finally met her gaze and shrugged. “Well, yeah. But now I feel guilty because you’ve been saving yourself for me or something.”
Dawn clucked and shook her head, which made her boobies jiggle as well, drawing my attention downwards. “I never asked you to save yourself. You’re a guy, Ben, and you’re my friend. I know how your mind works and I knew you’d be led around by your dick quite a bit. After all, I saw how easily you got wrapped around Dayna’s little finger.”
I winced at the memory and then Dawn frowned, looking at me a little harder. “Ben, you said before that you were afraid of being with me because you’d screw it up. That you’d screwed it up before. You weren’t just talking about Dayna, were you?”
I shut my eyes and winced, nodding my head ‘no’. The subject had now gotten so painful for me that my cock completely went limp and managed to slip out of Dawn’s pussy, followed by a puddle of mingled cum that ran out and began to dry in our crotches.
Dawn got up and moved to the side, a serious look on her face as she stared down at me. “Ben, did you cheat on one of your girlfriends?”
My wince and the way I dropped my head back against the blanket was all the answer she needed.
She arched an eyebrow. “More than one of them?”
I grimaced and nodded.
She looked at me dubiously, “All three of them?”
I bit my lip and Dawn just stared in disbelief at me. “Three times? You didn’t learn from your mistakes and you did it three times?”
“Well, in my defense,” I sputtered. “It was only twice.”
“Then how do you cheat on three girlfriends?”
“I was dating two of them at the same time,” I gave her a helpless look. Then I quickly added for clarification, “They both knew about it. They were best friends who wanted to share me.”
“Okay Ben, I’m serious now,” Dawn looked at me. “Tell me everything.” She slid across the blankets, grabbing a hand towel to wipe herself up and then started cleaning me as well.
I winced and turned my eyes away, searching for something to say, but Dawn grabbed my head and turned it towards her. “Come on, Ben. This is me, Dawn. We’ve never had secrets from each other and I don’t want to start now. I LOVE you. I truly believe that nothing you can say to me will ever change that. Look, you’re embarrassed because you cheated. I can handle that. Hey, I had sex with you when we both were dating other people. You at least seem remorseful about it and that’s a start. What’s past is past. Work with me, Ben. Tell me everything and I promise I’ll still love you in the end.”
I exhaled, feeling all the fight in me evaporating away. This was Dawn. I did love her, and she deserved to know everything about me. I sighed and said, “Okay. But no names, remember?”
She nodded. I’d kept Keira a secret and Dawn had never pressed me. I’d tell Dawn my history, but I wouldn’t say anything that might come back to haunt one of my past lovers. It just wasn’t in me to do so.
“Okay. Now how many girls have you had sex with?”
I raised my eyebrows. “Uh, gimme a second.” I didn’t have the exact number readily available, and I’d have to think back and count. “And, well… it sort of depends on how you count.” For example, I had girls give me blowjobs without getting to full intercourse. Those didn’t really count, did they?
Dawn rolled her eyes at me, so I just shut up and did the math for full intercourse: Keira, Megan, Cassidy, Brandi, Adrienne, Mizuho, Donna, Stacey, Mandy, Abbie, Allie, and Summer. Blushing, I said, “Twelve.”
“Twelve???” Dawn looked incredulous.
“Well, not including you and Dayna. That’d be fourteen,” I stammered.
Impossibly, Dawn’s eyes got even bigger. “Fourteen???”
And then I thought of Elyse, Candy, Lynne, and even Brooke. If I was really going to be honest, then yes, they counted. “And technically, if you count oral, then it’s eighteen.”
Dawn’s jaw dropped. “Ben. It’s been less than a year since I last saw you. How the FUCK did you do all that?”
I blushed. “It’s been an interesting year.”
We didn’t quite get through everything. Dawn kept asking questions and we kept getting side-tracked; but by the time we needed to start heading back, I’d spilled much of my sexual history.
I’d also started to relax my fears of losing Dawn over the mistakes of my past. She’d said she wouldn’t judge and while I could see her jaw clenching when I detailed some of my transgressions, she did seem to accept them as foibles from my past and her love for me still shone through.
For example, one of the first things I explained was Adrienne’s initial seduction after she trapped me in her garage. Without going into detail, I explained how the hottest girl in school pretty much stripped naked and threw herself at me, looking for nothing more than a lusty fuck and a few orgasms. Dawn rolled her eyes at how easily I was seduced despite having two happy girlfriends, but she didn’t get upset with me.
I suppose that was what made Dawn so much different from any other possible girlfriends. We knew each other so intimately already and this one situation from my past was just a drop in the ocean of experiences we’d already had together. Yeah, it caused ripples, but the bulk of Dawn’s opinion of me had already been formed.
Conversely, if I ever told that story to a girl I barely knew, or even a girl I was getting close to but didn’t know very well just yet, I would soon find myself staring at her back as she stomped away from me in disgust.
As time went on, going through my history with Dawn, I got more and more comfortable with her. I was less hesitant and less embarrassed about the things I’d done. Originally, I planned to feed my sexual past to her in small doses. I wouldn’t hide anything from Dawn, but I didn’t intend to give it to her all at once either, stretching out the different tidbits over the next month or so. But we kept going and going and I even told her about my winter break affair with Brandi.
“Wow…” Dawn said in amazement. “I mean, I’ve no grounds to say anything since I was having sex with my older sister long before you, but… wow… You actually had sex with Brandi?”
Wincing and peeking at Dawn with one eye, I hesitantly wondered, “You’re not disgusted?”
“Not at all,” Dawn blushed and smiled. “Actually, it’s kind of a turn-on to picture it.”
I knew how she felt. Talking so much about getting laid had given me a new erection. But we were still in the conversation, so I kept going. We chatted on and got through some of Brandi’s post-shower stripteases. By now, I was no longer in confession mode. I was just telling stories with an old friend about some humorous and sensual episodes.
I was in the middle of telling Dawn about how one night, Brandi just hopped onto the kitchen counter while everyone was asleep and ordered me to eat her. I thought it was hilarious that my sister kept drinking her coffee while I tongued her slit, but it just made Dawn horny and she finally grabbed my head and planted one of those volcanic kisses on me.