RPF - The Roommate’s Young Girlfriend

For this week’s RPF, I laid out her black satin pajamas, and a leopard-print bra. I had noticed her wearing the matching thong to work that morning. These were her instructions:

Today is Role Play Friday, and I have a doozy. Take a shower, put on some perfume.

You: You are Annie, high school senior, dating Tim, a college sophomore and notorious “player.” You haven known his reputation, but he has been mercilessly trying to get you to give up your virginity. Tonight, after an ugly fight yesterday, you’ve decided to give him what he wants as a grand surprise.

Me: I’m Don, Tim’s roommate. We’ve known each other for as long as you and Tim have been together. I know Tim came home after the fight steamed, and decided to stop putting forth the effort with you. Deciding he wanted to get laid, he set up a date with Heather Morris, notoriously the easiest girl in college, and known as such to both of us.

I come home to your surprise for Tim. I don’t want to sell him out, because I’m a good guy, but I don’t want you taken advantage of, either. Plus, someone should comfort you on a night like this.

Can’t wait to see you.

-Master

P.S. - Keep your panties from this morning on.

I got home to a quiet house. As I closed the door I heard a voice call from the inside. “I’m in the bedroom.” My heart sank as I walked back. “I’m sorry about the fight we had.” I walked in to the bedroom to see Annie. She looked up at me. “Oh. Hi.”

I blushed. It was bad enough catching my roommate’s girlfriend in her sexy surprise for him, but it was more because I knew why Tim wasn’t home. In a fit he had called up Heather the Sure Thing, and he was over at her place tonight. So, now, apart from the, oops, I’m sorry’s…now I needed to tell Annie that Tim wasn’t going to be home. And, by the looks of it, he was going to be really sorry. He and Annie had been fighting about her virginity and his desire to take it. Apparently she had finally decided to let him have it. Honestly, I had always really felt bad for her. She is a lot better than Tim. So, I had to break it to her, I guess.

“Tim’s not going to be coming home tonight.” Seemed like I had to tell her. Couldn’t just leave her waiting all night and find him coming back in the morning reeking of what, and whom, he had done the night before.

“He’s not?”

“No,” I replied.

“I thought he was hanging out with you,” she said.

“Tim and I don’t really hang out much,” I said.

“But you guys go out almost every weekend!” she replied. Uh oh. Deep breath time here. Tim had always told me that since Annie wasn’t sleeping with him yet, she was okay with him going out and getting some on the side, since he needed it so much. Now, I was confronted with the truth. Why am I having to clean up his mess?!

So, I sat down next to her as she sat up on the edge of the bed, and explained. I felt awful about it, because she’s a beautiful girl, and so sweet. This was one of the few times I had really envied him, and I hated the thought that he was going to be giving her a sour welcome to the grownup world. It had actually been sort of grimly satisfying to know that she was holding out on him. I was hoping she would wake up to it all in time. Now, apparently, just in time.

She seemed to take the news pretty well, but she was obviously upset. I cradled her against me trying to comfort her. Her perfume was wafting up, and it was heavy and intoxicating. She had really gone all out for him, and clearly wanted her first time to be a big deal. What a bastard…she sighed, “Well, I guess I’m glad I found this all out before.”

I was unconsciously staring at her breast through her half-open pajama top. She caught me and started to cover up. “I can’t believe I’m showing my boyfriend’s roommate…well, ex-boyfriend’s roommate my breasts.” I had to smile.

“It’s okay, they’re nice breasts.” She laughed a little.

“How do you know? You haven’t seen them.” It was nice to see her sense of humor waking up.
She started buttoning back up much to my regret.

“Well, from what I have noticed when you are over, I have always though that they were really nice.” Slowly, the conversation turned back to how beautiful she is, and how much more special she is than the other girls he brought back. So many people just using each other, and here was this gorgeous girl who really cared. As I held her, and told her that I could tell how special she was, I stroked her face a bit, which she seemed to welcome. She really did deserve better. The eye contact became more prolonged, and, finally, I took the chance. I kissed her.

She kissed back. Things became intense very quickly. I was holding her face against mine, our tongues sliding across each other as I began to want more. Here I was, suddenly just another guy who was trying to get in her pants. But I had wanted her for so long, and this was my chance. She breathed that it was so wrong, but she didn’t want to stop. I started unbuttoning her top, and she didn’t stop me. I pushed the satin off her shoulder and took her breast in my hand. She gasped hard, as her nipple rose through her bra cup.

“I’ve never felt like this before!” she panted.

“It only gets better from here.” The chemistry was incredible. She was completely relaxed, surrendering her body to me without a second thought. I fumbled with two hands taking her bra off, and she happily shrugged it off. I pulled her face to mine as I finally touched the skin of her breasts. She moaned, loudly, again how it has never felt like this. I leaned down and licked the nipple. Now she was gasping hard, her breaths ragged and out of rhythm. My hand went to her pajama pants…do I dare? She has been through so much. I could see in her face she wanted them off, so I pulled them down, and then laid her back on the bed, scooting her up so her legs were on the mattress.

We were now getting into dangerous territory, but she was completely happy to forge on ahead.
My hand reached down to her panties, almost on its own. She moaned sharply. This couldn’t be new territory for her, but clearly this was a new kind of intensity. I hesitated, then tugged the material aside to touch her directly. She was writhing beneath me now. “Have you ever been kissed down here?”

“Sort of. Tim did, but I wasn’t really into it. I want to try now.” I smiled, and down I went. Her hips arched under my face and she groaned as my tongue danced on her clit. “Oh god…” Suddenly, I was happy, I was proud. She was finally being treated the right way, and being loved by a man. This might have started wrong, but it was so right. I stood up, she looked at me as I unbuttoned my own shirt. No fear was anywhere in her eyes. She wanted this, and so did I. I pulled my jeans off, leaving my underwear. I looked at her.

“You can still say no.”

She smiled. “I don’t want to.” I smiled, and stripped naked before her. I laid back on top of her. She was wet, and I pressed in slowly, giving her just a little bit of the tip, just enough to start her muscles stretching. She gasped and pulled me closer, so I pressed in farther. She was only too happy to keep taking me in. In two more motions, she had taken me in, her first man. I smiled down at her.

“Welcome to your womanhood.” She laughed and held me closer. I began sliding on her now, keeping my hips low to rub her clit, and moving slowly to let her grow into this. Her muscles were strong around me, and even though I wanted this to be focused on her, and let her have her first time be perfect, I was too turned on. I was simply incapable of suppressing the orgasm. I continued to push, and I was telling her I was going to come. She only pulled me in tighter…she wanted to feel me. I came in staccato bursts of liquid inside her. Her eyes widened as she felt it exploding inside her. I laid still on her for a moment, but then knew I needed to take care of her. She deserved to have it all for her first time. I resumed my motions, and her moans were louder, as the feel of me coming inside her had aroused her. She moaned that she was going to come, and her powerful muscles squeezed my now-semihard cock inside her, almost squirting me out.

Her orgasm was beautiful, and I was proud to have been there for her. We curled up under Tim’s sheets, leaving a stain on his comforter. The air was saturated with the smell of our love, and thick with moisture as we laid in his bed. We decided, then, that this experience merited repeating, and that we should be spending a lot more time together.

—

The most amazing thing about this role play was how we each seemed to inhabit our characters, and how that mood so strongly affected how it felt. It so much like our first time together with that, with novel intensity of the touch of stranger. I look forward to seeing what my imagination dreams up for the next RPF.