First Time with Dawn

The summer I was 18 I was dating 20 year old Jenny, who was also sexually involved with her roommate, Dawn. I had always encouraged Jenny to explore her bisexual side, and she didn’t hesitate. We knew that inevitably the three of us would play together, it was just a matter of when.

The night finally arrived at Jenny’s insistence. It was a Saturday night, and she took Dawn and I to see a movie. The movie was irrelevant; Jenny just wanted the three of us in a dark public place. Doing things in public was one of her kinks.

The three of us sat side by side, Jenny in the middle. She started with a hand on each of our legs, and we both started touching her. Occasionally my hand and Dawn’s would touch, and we felt each other out, withdrawing, fighting for territory. Soon Jenny took control and guided both of our hands. Dawn leaned in and started kissing Jenny, I did the same, kissing Jenny’s neck while she was turned the other way to kiss Dawn. Then she would turn to kiss me and Dawn would kiss her neck. Needless to say, we didn’t make it to the end of the movie.

We drove back to their apartment and as soon as we were inside Jenny took over again. She took us both by the hand and guided us to Dawn’s bedroom, since Dawn had the bigger bed. The three of us stood there, our bodies pressed against each other, kissing, Jenny in the middle. She asked “Do you both trust me?” We both indicated yes, but also curious about what was in store. “Good, so you’ll both do whatever I say.” That wasn’t a question.

Jenny moved to a chair in the corner of the room and undressed before sitting down.

“Now kiss each other and undress each other. And don’t talk.”

We moved to each other and didn’t hesitate. She was shorter than Jenny, so I had to crouch lower to meet her lips. I grabbed her ass in both hands and lifted her onto her toes. She wrapped her arms around my shoulders and pulled herself closer. I broke the kiss and lifted her shirt over her head, tossing it to the floor. She wasn’t wearing a bra, and I got a first look at her soft, pale nipples that Jenny had raved about. She lifted my shirt and I helped her pull it over my head. While I did that she made short work of my jeans, pulling them down along with my boxers in one motion. She started unbuttoning her shorts before Jenny interjected “No, he has to do it.” I took the direction and unzipped her shorts. I got onto my knees and slid her shorts and panties down to the floor. She stepped out of them and kicked them to the side.

I was now eye level with her tits and started licking and sucking them into my mouth. She gasped. I reached around her and gripped her ass and pulled her closer to me. She gently placed a hand on the back of my head and cradled it like I was a newborn. After a moment, Jenny said “Get on the bed.”

Dawn held my hand as I stood, and we moved over to the bed. I looked back at Jenny who was still naked in the chair. Her legs were spread and she gently touched herself, teasing herself, not wanting to get off just yet. I sat on the edge of the bed and swung my legs up, laying down. Dawn laid next to me and we resumed kissing. Our hands explored each other, and she gently brushed against my cock, teasing it and showing incredible patience that I wasn’t used to.

“Dawn, sit on his face.” She pulled back from our kiss and locked eyes with me, and smiled. Wordlessly, she rose up, standing above me. I looked up at her sweet pink pussy, with just a whisp of red hair. She crouched down and expertly placed herself just a tongue-length above me. I normally would eagerly dive in, but decided to go slow. I wanted this to last and I wanted to remember everything.

I reached out and teased her with the tip of my tongue, making sure that there was plenty of saliva to keep things slippery. It wasn’t needed though, as she was already so wet that drips were falling on my chin. She started sliding her hips back and forth, and lowering herself more so that she was firmly pressing against me. I picked up the pace and started alternating between teasing her clit and slipping my tongue as deep into her as I could. Each time would elicit a gasp.

From the chair, a groan, then “Good, now stand up and turn around, then sit on his face again.”

Dawn did as directed, lowering herself onto my face again, this time aligning my tongue with her tiny pink asshole. I didn’t hesitate and resumed gently licking her and teasing. My hands were now able to reach up and grab her hips and move over her body. Her moaning grew louder as my tongue worked her over. She pushed down and I responded with increased pressure from my tongue. I could feel her open ever so slightly as I applied pressure.

Soon I was hearing more coming from Jenny, the sounds of panting and the unmistakable sound of her fingers sloshing in and out of her wet pussy. So clearly all three of us were enjoying this.

“Fuck, not yet” I heard Jenny say, presumably to herself, as the sloshing abruptly stopped. “Ok, Dawn, lay down next to Jason.” She lifted herself off of me and laid next to me. She turned to me and kissed me deeply and passionately, before Jenny stopped her. “No, don’t kiss. Just lay there.”

Jenny stood up and opened one of Dawn’s drawers, taking out a small white vibrator that she obviously was familiar with. She handed it to Dawn and then sat back in the chair. “Both of you, masturbate for me. Don’t hold anything back.”

That was the only direction forthcoming. I reluctantly reached down and started lightly stroking my cock. Dawn turned on the vibrator and started rubbing it against her clit. She reached up and brushed her fingers against her nipples. The sloshing sound from Jenny resumed.

After a minute, more direction from Jenny. “I told you to not hold back. Stroke it like you mean it!” Clearly I wasn’t being enthusiastic enough. But honestly this was the first time I’d done this for an audience, especially an audience of two. I repositioned on the bed, getting more comfortable, and convinced my brain to let go, that she wanted this, that they wanted this. I started stroking harder now, longer strokes. I glanced at Dawn and saw that she was staring at my cock while she slid the vibrator in and out of her pussy. Jenny was also staring at my cock while her fingers worked herself over. She caught my glance and smirked before pulling her fingers out and bringing them to her mouth for a quick lick.

I resigned myself to what was happening and went with it. I stared at the ceiling and started stroking myself with the expertise of, well, really any other 18 year old male… Both women were groaning louder now, and I didn’t hold back, letting my groans join theirs’. I knew it wouldn’t be much longer now.

When the time came I followed directions, I didn’t hold back. I groaned loudly as the first spurt shot strait in the air. After what seemed like an eternity, it landed with a splash on the left side of my stomach. Dawn, who was to my left, must have gotten part of it also, because at the same time she let out a yelp and her body jumped. The subsequent spurts were also sent in the air and landed on Dawn and I.

Fortunately she was right behind me, and her orgasm hit just as mine was starting to subside. Her body jerked and bounced against me. I didn’t see a fountain of cum shoot from her, but the change in noise and increased sloshing told me that she nearly squirted. At minimum those sheets would need to be replaced. I glanced at Jenny expecting to see the same. But she just stared with a smile on her face, her hands at her side.

I wanted to kiss Dawn, or at least nuzzle against her and feel her body, but we were waiting on directions from Jenny. Eventually she stood from her chair, leaned over the bed and gave us each a passionate kiss. She walked out of the room and returned a minute later with a small towel. She tenderly wiped us both clean and kissed us again. Then she laid in bed between us and pulled a blanket over the top. We got comfortable and she finally whispered “thanks” before we dozed off.