Crossing a Boundary

"I'm looking forward to tonight," I said, kissing my boyfriend Eric on the back of the head as he poured some pretzels into a bowl.

"Yeah, me too," Eric answered. "You better hurry and get ready, they'll be here any minute."

I threw a dish towel in his direction. "Fuck off, I AM ready!" I said, holding out my arms and giving a quick twirl. "These jeans and shirt are cool. You know what's wrong with you, Eric?" My boyfriend turned to look at me. "You don't know what's cool anymore. Old man." I laughed and winked.

My boyfriend laughed. "40 is hardly old, youngster," he smiled.

I really loved my boyfriend. We'd been together for four years and this was our first house together. I was quite a bit younger than him though, 12 years to be exact. I met him when I was 24 and he was 36.

Eric might be 40, but he was gorgeous: nice toned body, lovely chestnut hair and just the right amount of stubble on his strong jaw. He got hit on by both guys and girls, and I always felt lucky to be with him. Me, I was more the indie rocker type - skinny, tall, messy-looking hair, clean shaven. My boyfriend loved my look, so we were a good match.

"Is everyone coming?" I asked, as put bowls of snacks on the table.

"Yeah, actually. I thought Jeff and Sam would flake out again, but they confirmed this morning. We'll have a full house," Eric said.

"But not..." I started.

"She's my sister, Ben!" Eric interrupted, anticipating what I was going to say next. I groaned. "She's not that bad!" Eric laughed.

"She's got the fucking hots for me. It's weird," I shook my head and stuck out my tongue.

"She's just friendly," Eric said, defending her.

"She's a slut," I answered, knowing I'd gone too far.

"That's not fair, Ben," my boyfriend said, seriously.

"She has a lot of boyfriends," was my reply.

"Yeah..." Eric didn't have an answer for that. "She's pretty demanding," he admitted. "She's a dominant personality and a lot of straight guys can't handle that."

Eric was right there. His sister Val was definitely a dominant personality. She was a rock chick with a big mouth. She drank and smoked, and ate guys for dinner. I might be gay, but I could see why she easily twisted guys around her finger - she had a great body, tall, curvy but athletic, big tits and a gorgeous face. I just wish she didn't flirt with me so much. I think she just did it to make me uncomfortable, but I could never tell.

By 9pm the party was in full swing. We had 21 people in our home, 23 if you included me and Eric, so it was pretty full but cosy. Most of our party were our gay friends and co-workders, but Val was there, plus my best friend Lucy and a lesbian couple who Eric had known for nearly 20 years.

Val was the life of the party as usual. She looked great tonight - she had her hair down and was wearing enough makeup to made her look sexy but almost slutty without crossing the line. She was wearing a tight faded Van Halen t-shirt and a skirt, finished off with heels. I sort of resented her for grabbing all the attention. She was showing all the different ways she knew to take tequila shots, and was currently standing on her head and asking my friend Tony to pour the shot into her mouth. She swallowed it (somehow) and fell to the floor, laughing. "Next time you can pour it into another orifice!" she said, spreading her legs and then closing them again, to Tony's horror.

As outrageous as she might be, I could see the appeal - she was really charming and sexy in the way she did everything. People naturally gravitated to her. I wished she would go and let me have my party back, but I knew she wouldn't so I took the opportunity to join my guests in tequila shots.

By 3am, most of our guests had gone. Eric's lesbian friends were staying over, and had gone to bed ages ago.

"I'm checking out," Eric said, giving me a peck and telling me to be a good boy and tidy up.

I laughed and smiled at my boyfriend. "Yeah right. This is a joint job now that we live together."

Eric winked and gave me another peck, then slapped his sister on the shoulder and headed upstairs to bed.

"Right, another shot?!" Val laughed, pouring three tequilas for the last men and women standing - herself, me, and Eric's co-worker Henry.

Henry was super-hot: early 30s, toned and fit body, chiseled features. I was really into him, Henry was into Val, and Val was into me. It was a weird triangle at play. I think Henry was only staying because he thought he could take Val home if he stuck it out long enough.

"Another shot!" Val exclaimed. I'd had so much to drink I was starting to think my liver would never forgive me.

We all did the tequila shot then Val asked Henry if he was gay. Henry laughed. "Uh. no. Why do you think that?"

"I didn't think anything," Val answered plainly. "I was just asking. So you've never done anything with a guy?"

"No, but the girls love me," Henry answered, trying to steer the conversation back to him and her.

"I dare you to kiss Ben," Val said, with a grin.

"But I'm not gay," Henry replied. "Plus his boyfriend is my friend."

Val was undeterred. "So what? It's just a bit of fun. You're both hot and I want to see you kiss."

"What's in it for me?" asked Henry.

"You can touch my tits after," said Val. "And Ben gets to kiss a straight guy. So we all win."

Henry thought about this then looked at me. I looked back at him and then he leaned in and kissed me. Gently at first and then a bit more. He wasn't a bad kisser. I could feel myself getting hard in my jeans. I hoped my boyfriend was sleeping deeply.

"It doesn't count if you don't use your tongues," Val said, lifting her shirt to show her boobs.

Henry leaned in turned his head to the side and slid his tongue in my mouth. I put my arms around him and he put a hand on the back of my head, running his finger through my hair. We kissed passionately for about 30 seconds before he pulled away. I didn't want it to stop.

"That's really hot," Val said, taking off her shirt. Henry reached up and touched her tits, playing with them before putting his face between them.

"Take off your bra," he said, kissing each breast before kissing up to Val's neck. She pulled away.

"No you need to do more first," she said.

"Like what?" Henry answered, clearly annoyed.

"Let's play truth or dare," Val answered.

"No, I'm not into that. Want to come back to mine for a bit?" Henry said slyly.

"I'm happy here," Val replied, putting a hand on my knee.

Henry left shortly after that, clearly disappointed.

"Why didn't you go with him?" I asked Val. "He's hot and he totally wanted you."

"Meh," she answered, pouring us each a large whiskey. "He's ok. I'm having fun here."

"I should go to bed. Eric will be waiting for me." I answered.

Val wasn't taking no for an answer. "My brother sleeps like a log and you know that. He won't mind if you're hanging out with your sister in law," she laughed.

"Uh, we're not married," I reminded her.

"Yet," was Val's answer. "You've been together ages. You feel like my brother in law."

"So more booze?" I asked, trying to change the subject. "You can really put it away."

Val laughed and threw an arm around my neck and leaned in for a kiss.

"What are you doing?" I asked.

"Giving you a kiss. I want to see what Henry was getting." I laughed at that, pulling back from her. I had to admit that I liked her confidence though. "Have you ever kissed a girl?" she asked me.

"No, actually. I always knew I was gay," I responded.

"And never curious or anything?" Val asked.

"Never been interested in women," I answered, the added "Sorry."

Val smiled. "Don't be sorry. Let's try it. Come on. I'm safe."

I looked at her, then she leaned in again and I let her kiss me this time. It was soft and gentle, I could smell a scent of vanilla, possibly from her perfume or maybe her shampoo. She did smell really nice, and her lips were very soft. It felt different from a guy.

After some soft and gentle kissing she slid her tongue between my lips and then pressed her mouth more firmly to mine. We started to kiss deeply, and our arms slid around each other.

Val pulled back, gently biting my lip before removing her lips from mine. I must admit, it was hot.

"Feel my tits," she directed, taking my hands and putting them on her breasts. I was a bit curious about them actually so I let her do it. They felt firm but also soft, held up by the soft pink fabric of her bra. "Do you like them?" she asked.

"Yeah," I said, running my fingers over them again and giving them a squeeze. "They're so big. And fun."

Val laughed at that. "I'm glad you like them," she smiled seductively, then reached behind her back and undid her bra. The fabric went loose under my fingers and she reached up to pull it off. Her tits were free now. They sat there, big and pert, her nipples hard and standing at attention for me. I stared. I'd never seen real breasts up close like this before. I was fascinated.

"Don't be afraid," Val said gently, almost in a whisper. "Touch them."

I reached up and did as she said, playing with her naked breasts. Val moaned gently and leaned in to kiss me again. I let her as I held her breasts, my hands circling them and my fingers gently tweaking her nipples.

I felt Val's hand wander down to my crotch. I gently pushed it away and kissed her deeper as an almost-apology, until I felt her hand trying again to get a feel of my cock. I was still semi hard from Henry, plus the erotic kissing and seductive voice Val was using.

"If I can't touch it," Val whispered, kissing me gently. "At least let me see it. Please."

Her saying please did it for me. I felt more comfortable, like she was requesting it, even if the reality was that she was totally in control. She poured me another whiskey as I unbuttoned my jeans, pulled down my briefs and pulled out my cock.

Val watched, sipping her drink. "Mmmm you're so big," she purred over her glass. In reality I was fairly average, maybe a bit bigger, at 7 inches. I wasn't fully hard though so I started gently stroking it for her.

"Mmmm I like how you do that Ben," she said, watching me and gently rubbing her tits. It was all getting a bit much for me.

"This has been fun but we should probably stop now," I said, starting to feel guilty for doing it, and with my boyfriend's sister.

"No please, not yet," Val begged. "At least lets finish our drinks and have a few more kisses." She leaned in to kiss me and I kissed back. She slid close and then reached over to touch my cock. This time I let her, thinking 'What the hell?' She stroked me gently while we kissed. My hands now free, I started to play with her tits again.

We were both really drunk. Val pulled her skirt up enough so she could climb onto my lap and straddle me while we kissed. I struggled to play with her boobs as she was pressed against me and had her hand underneath her, still stroking my cock. "Are you uncomfortable like that?" I asked.

"No. Kiss my tits," she commanded, pulling my face into her cleavage. I started to kiss her boobs, moving over to her nipples. I kissed and then gently sucked them, making her moan. 'What the fuck am I doing?' I thought. 'I'm going to lose my gay card.'

Val's hand continued to stroke and squeeze my hard cock until I felt a little pressure on my dick and then a different sensation. My cock felt warm, a soft and silky warm sensation like its spreading down my cock from the top down my shaft. Val tilts her head back and is taking in a deep breath, and as her hands move up and around my back I realise then that she's pushed my cock inside her.

"Oh shit, no!'" I say. But Val has fully slid down on it now and I'm all the way inside her. She kisses me to shut me up and starts moving on me, rising and falling back down, fucking herself with my cock.

I moaned through her kiss, partly because I was trying to tell her to stop, and partly because it felt really good. It was like nothing I'd ever felt before, like her pussy was pulling on my dick as she came off it, then softening again as my cock slid in deep.

"We have to stop. This is so wrong," I gasp into her ear.

"But you like it," she replied.

"I'm gay," I respond.

"Are you?" Val replied, kissing me again and pulling me over so we're laying on our sides on the sofa.

It's much more awkward laying like that now, and my cock slides out. Val bites my lip and looks into my eyes. "Fuck me, Ben," she says.

Despite myself, I'm actually feeling turned on. I adjust us on the sofa so Val is on her back and I'm over her. She looks at me, "I said fuck me," she commands.

"You're such a dirty naughty girl," I tell her.

"Oh, I am baby," Val says, "Punish me." I look down at her, legs spread, me between them. I now feel in control, even though I know she still is. This is all part of her game. And I'm totally falling for it.

"You're just a dirty slut aren't you," I say, shocking myself with my tone. I rub my cock on her clitoris and Val moans.

"I want you inside me," she says, her body moving under me. "Fuck me, I need it." she moaned.

My head is spinning but I take my cock and rub it on the wet lips of her pussy. It's inviting me inside, my hard gay cock. I'm about to make a decision that I can't turn back from.

I push gently and the head of my cock disappears into the soft folds, pulling me inside her cunt. I sink deeper inside her and Val moans, and I realize that I want this as much as she does.

I push my cock in deep, then start to fuck her, picking up speed until I'm pounding her pussy. I'm fucking my boyfriend's sister, my first woman, and I am loving it. Val is in ecstasy underneath me, moaning softly and trying hard to keep quiet so we don't wake her brother. "I love you in my pussy," she sighs.

I thrust deep and feel myself getting close. As much as I don't want to cum yet, I feel it getting closer. "I'm so close," I tell Val, getting ready to pull out and shoot all over her. She pulls me in and kisses me deeply, wrapping her legs around me as I push deep inside her pussy.

"I want to make you cum," she moans, lifting her hips as I'm thrusting my cock into her. And then it happens, I'm cumming, cumming deep inside her pussy and it feels so good. "Yeah cum inside my pussy baby," Val moans and starts to cum too, her body moving underneath me as we both climax.

We sink to the bed and kiss again. "How do you feel?" she asks, kissing me.

"Fucking great," I smile. "I can't believe I just fucked a woman." I add.

"I'm glad I was your first," she says. "And hopefully second."