Late Night Truth or Dare Ch. 01: Bobby

"Grab my breasts, Bobby. Pinch my nipples."

I always prided myself on my ability to take orders, especially in the bedroom. Some guys needed to be in charge, but I was more comfortable doing what I was told.

Obeying her command, I sat up, trying not to shift my cock as Ashley continued to ride me. I slid my hands from her hips up to her breasts. I took my time and teased as I slipped over her ribs -- barely noticeable compared to Candace's -- until my fingers pushed against her side boob.

I appreciated the heft of her breasts as I cupped them. They were both large and dense, something I found more pleasing than their light and fluffy counterparts. I could feel the thick tissue as I pushed my fingers into them and my nails started to dig into her skin.

"The nipples, Bobby. Pinch the nipples," Ashley called out between deep breaths.

She was nearing orgasm and needed me to push her over the edge. I hesitated, not wanting this to end, not yet at least. As obedient as I was, I tended to be a bit of a brat, opting to disobey when I thought it would produce a better outcome.

Ignoring her nipples, I gripped her breasts tighter. I pulled her against my chest, our sweaty skin sticking together. Leaning forward, I kissed the side of her neck. She smelled of vanilla, and her supple skin contracted as I nipped at her neck, gently taking her between my teeth.

Ashley's gyrations increased. She was growing closer and closer. She was going to cum with or without my help, so I might as well make sure it was the best she could have.

I shifted my hands, taking her nipples firmly between my fingers and clamping down. I increased the pressure as I went, not knowing where her tipping point between pleasure and pain was.

I never found out as she erupted into orgasm long before I reached her limit. Her cunt might have felt loose when she first slid on top of me, but now she clenched down as none of the others had. Her pussy gripped my cock as she shivered on top of me. I had to dodge her head as she flung it back in pleasure, screaming towards the heavens.

"Oh, God. Oh, God. Oh, God. Fuck yes. Harder, harder, harder."

I obeyed, continuing to tighten my grip on her nipples, pulling them outwards, stretching the skin of her breasts as I went. One final gasp escaped her lips as her body went limp, forcing me to support her as she swayed forward.

I leaned us both to the side, easing her down as we descended towards my mattress. My cock was still embedded inside her as we spooned, her post-orgasmic body feeling lifeless as I held her.

I softly kissed her shoulder before she turned her head, meeting my mouth with hers. Our lips locked as our tongues reached for each other's. The kiss was somewhere between intense passion and gentle aftercare, lasting for as long as we could breathe.

As with the others, she rolled forward and slipped from my bed too soon, stopping at the door and looking back at me.

I was too tired to protest.

"Thank you, Bobby. You really are a great lay," she said before blowing me a kiss and disappearing down the hall.

It had been a long night, and I was sobering up, both of which caused me to quickly tire despite my raging hard-on. As much as I wanted to relieve myself, I knew it could wait until the morning.

My eyes drifted shut as I felt the cold air of the vent wash over my damp body. There was no need for my covers, not yet, not until I recovered from the four gorgeous girls who had just used me as a prop for a risqué game of chance.

I should have been upset, but who could complain about fucking four of your younger sister's friends, especially without a condom. I just needed to remember--

*****

I don't know how long I was asleep when, once again, I was awoken by a naked body on top of me.

As I ran my hands along their slender body, gliding over their flat stomach and cupping their small tits, I knew it was Candace back for the second orgasm I promised her.

Part of me wished she had waited until another night to cash in, but as soon as my cock slipped inside her, I was relieved it was now.

I felt sore as she slid her tight cunt over my member. I had been used and abused all night, and it had taken its toll. It was not until she settled into a smooth rhythm that I forgot about the discomfort and focused instead on playing with her pert boobs.

There wasn't the urgency of our first round.

The game was over.

I am unsure how it was scored or if anyone won or lost. I felt like a clear winner, but I don't think I factored in the final standings. Dee was the only one to get my sperm, but was that the punishment or the reward?

It was a question that would go unanswered and was quickly forgotten as I realized I no longer had to lie there and let Candace ride me. I grabbed her by the waist and rolled to one side. I found myself on top of her with her legs wrapped around me, pulling my ass towards her.

I lowered my mouth to her nipple, cupping the other breast, as my free hand reached beneath us, grasping her ass as I fucked her, fully taking charge for the first time tonight.

I ground against her as I slid in and out, but the friction was not enough. She slipped her hand between us, fingering her clit, freeing me to focus on pumping into her.

She felt shallower than before, but I was now on top, providing me with a different angle of attack. My shaft bottomed out, and the tip of my cock collided with her cervix. If I came, my swimmers would have but a short distance to go. I needed to make sure to pull out.

I was worked up. Despite my earlier orgasm, I was ready to cum again. Being fucked five times by four girls would do that to a young man. I wouldn't last long, but I hoped to make Candace cum first.

I picked up the pace as she gripped my hair, pulling me into her breast and forcing her nipple between my teeth. Instinctively I gently bit down, proving to be enough to push her past the threshold.

She grabbed my ass, digging in, urging me to fuck harder as she panted, not screaming out like before. This orgasm was different and seemed to preclude her from calling out, but it was no less intense. If anything, it was more powerful.

Her body quaked beneath me, and her cunt clamped down even harder than Ashley's, milking my cock as I drove inside and clinging to me as I pulled out.

It was too much to take. I was going to cum, but I needed to pull out. The game was over. There was no need to risk impregnating Candace, especially since I had already cum inside her friend.

How would I explain that to my parents? One unwanted pregnancy was bad enough. Two would be indefensible.

I waited until the very last minute, not wanting to cut her orgasm short. I knew I was risking mistiming my actions, but she was still shaking below me.

I was caught off guard when I finally moved to withdraw from her. Candace, still gripping my ass, pulled with all her might, wrapping her legs around me to assist, preventing me from pulling out.

My cock twitched and jerked as the first load shot forth, still inside her. It was too late, and I decided to go with it. Starting to pump again, I got the most from the risky finish.

I pushed my head against her chest, forgetting about sucking on her nipples. I inhaled deeply and let out a reverberating groan. It was one of the best orgasms of my life, much more powerful than with Dee.

I felt a longstanding connection with Candace like we were bonded together. The sex was powerful, but this was more than lust. It was as if our bodies knew what each other would do. Like we had spent a lifetime studying each other.

Her body stopped convulsing, and my cock ceased twitching. I collapsed on top of her, my face nuzzling into the crook of her neck. She turned her head, our lips meeting.

Our kiss increased in intensity, and I slid my hand behind her neck. Then up to the back of her head. Instead of the tight curls I expected, I was met with a bun of straight hair.

This was not Candace. How was I mistaken? None of the other girls had a body that was anything like hers. No one, except for my sister Sarah.

As shocked as I was, I did not break from our kiss. I ran my options over and over in my head as our tongues continued to dance. I instinctually wanted to freak out, but I knew it was too late. The damage had been done.

Not only had we had sex, but I had cum inside her. Did this mean she had always wanted to have sex with me? Was this simply her being drunk and coaxed into something stupid by her friends?

There would need to be a discussion about the morning after pill, but that could wait for tomorrow.

I decided that for tonight I would appreciate the naked body next to me, and the details could be worked out in the days to come.

We lay nested in each other's arms, not saying a word. There was no indication of regret from either of us, only love. We had always been close, at least for siblings three years apart, but this was never something I envisioned happening.

A growing part of me wished that this was not some fleeting, drunken hookup and that it was something sustainable, at least for the next four weeks.

When I woke, Sarah was gone. I took a minute to reassure myself that the previous night had been more than a dream.

Everything that happened after the Uber dropped me at home seemed unbelievable but the stains on my sheets and the crustiness on my cock suggested otherwise.

I rolled over to find something on my nightstand catching my eye. I smiled as I reached over and picked up the key to the liquor cabinet.