Pleasing My Sister-in-Law

The next morning, I started to wake up when I felt a hand on my groin under the sheets of the bed I was sleeping in. I slowly opened my eyes up to see my girlfriend, Jessica, laying on her side and looking at me.

"Good morning, beautiful," I said, leaning over to kiss her forehead.

She held one of her fingers on her free hand up to her mouth to shush me and whispered, "I have a plan today, but in order to do it, you need to stay quiet, OK?" I nodded my head, yes, as she slipped her hand inside my boxers and wrapped it around my growing cock.

"I can hear Hannah moving around out there. Let's make this quick, and I'll text you the rest later," Jessica whispered before she moved her body down and under the covers. I felt as she pulled my boxers down, exposing my rock-hard, six-inch-long cock. She wrapped her lips around it, swirled her tongue around the head of my cock, then started to slide her mouth down the shaft, getting at least half of me inside her.

She kept her hand on the lower portion of my shaft, rubbing it up and down, while her mouth worked on the upper part. I lifted up the covers so that I could watch her as she blew me, but I couldn't see much more than the top of her head. Jessica bobbed her head up and down the first couple inches of my cock, following the same speed as her hand on the bottom portion. I could just feel her breasts pushing into my legs as she leaned over them, and I resisted the urge to reach down and touch them.

I started to wonder if she wanted to do my idea from the night before, cumming on her face and seeing how her sister reacted to it. My mind started to race as I thought about all the possible plans she had for the day, and it wasn't too long before I was whispering to her that I was close.

Not sure what to expect, I lifted the sheets as high as I could and watched as she continued to work my shaft with her mouth and hand. She finally looked up at me, her hazel eyes making contact with my blue eyes. Seeing the passion on her face, I told her I was coming and watched as she took as much of me in as she could and used her hand to pump the cum out of my cock and into her mouth.

Jessica worked quickly to swallow the cum as it shot out of my tip and used her tongue to lick up the last little bit of it before pulling my boxers back up and over my cock. As she came out from under the sheets, she kissed my cheek before saying, "Good morning!"

As I recovered in bed, Jessica got up, threw some clothes on, and waved bye to me as she opened her bedroom door and left the room. I could hear her and Hannah talking as I slowly rolled out of bed and got dressed to go join them.

The rest of the morning was spent with the three of us taking turns in the shower, packing the last little bit of Jessica's belongings, and loading the moving van.

At some point, Jessica told me to take a break and look at my phone. I had a text from her that said, "So, my plan today, after you told me about Hannah's experience with giving a blowjob, I want you to try to convince her to give you one. I don't think it'll be too hard after talking to her. I'll tell her to ride back in the van with you while I drive my car to Utah. If she doesn't want to give you one in the van, I can always find an excuse to leave later today."

"Are you serious?" I texted her back.

"Of course," she quickly sent to me. "It'll be fun."

We had planned to leave around noon that day and were successful with it. Hannah jumped into the passenger seat of the van after walking to the apartment office with Jessica to turn in her key. We waved goodbye to Jessica as she pulled out of the complex first, and I followed behind her.

When we were on the highway back to Utah, my mind was racing with what to say to Hannah when she said, "I'm kind of surprised you and Jessica didn't want to ride together." I asked why, and she said, "I just figured you two would want as much time together as possible."

"Maybe she's just wanting me to get to know her sister even better," I suggested.

"Why? You're obviously comfortable enough around me already," she said.

"What do you mean by that?" I asked her.

"You know, the conversation we had yesterday, plus the stuff you and Jessica did last night. You wouldn't do that if we weren't comfortable around each other," she said.

"Oh, you heard us last night?" I asked her, and when she answered affirmatively, I asked her, "Did it turn you on?"

I saw Hannah blushing, and she quickly looked away from me. She quietly said, "Is it bad if it did?"

I shook my head and said, "I don't think so. I would think it's a normal human reaction to feel something. Especially after spending the day talking about it, then hearing it."

"Yeah, but she's my sister, so that makes it kind of weird. I should be grossed out," Hannah said.

"If you take your sister out of the equation, what do you think then?" I asked her.

"I don't know. Sex is supposed to be between two people; that's it," she said.

"So, what if I told you that while I was having an affair with Jessica, I was also sleeping with somebody else?" I said.

"You mean your wife? Yeah, that's what an affair is," she replied back. "Isn't that how you ended up divorced?"

"Nope, not from sleeping with Jessica. I got caught with somebody else. Well, not really caught. The other person told my ex, leading to the divorce," I said.

"Are you serious? That's messed up," Hannah said. "Does Jessica know?"

"Jessica not only knew about it; she would watch us some times, or we would send her a video or a picture. And, one time, all three of us shared a hotel room together," I told her.

"Oh my gosh!" Hannah exclaimed. "I just can't."

"I hope that doesn't make you think any less of me or Jessica. I'm just trying to explain that, even though your sister was involved, it is perfectly normal to get turned on by hearing somebody else having sex," I said.

"No, I don't. I just don't even know right now," Hannah said.

As Hannah stared out the window, trying to process everything I just told her, I drove on in silence. I was wondering if I went about this the completely wrong way when Hannah turned to me and asked, "Is it still happening? Is the other girl back in Utah?"

"Yeah, she's back in Utah, but we had a falling out a few weeks ago, unfortunately," I told her.

"So, what kind of pictures and videos would you send to Jess? You and the other girl having sex?" Hannah asked me.

"No, it was mainly of blowjobs. I asked Jessica once why she even liked them, and she said that she just liked to see my cock in action," I said, seeing Hannah briefly wince when I said cock. I also caught her glancing down at my groin and, feeling myself starting to stir down there, asked her, "How serious were you yesterday when you asked to see it?"

Hannah looked down at it again before saying, "I don't know. It's not like I haven't seen a penis before. And, how would you show me? While you're driving?"

I smiled and said, "Sure. It wouldn't be the first time it's been out while I was driving."

"Seriously?" Hannah asked. "With Jessica?"

"I don't think so. I mean, we've definitely done stuff in a car, but I don't think it was while we were driving," I said.

"Oh. Well, as curious as I am, I don't think it would be a good idea," she told me.

"I just want to be clear here: I would never force you to do anything, but I am curious why you think it's a bad idea," I asked her.

"Because you would probably want me to do something," she said. I asked like what, and she said, "Either a handjob or a blowjob." I shrugged my shoulders, but before I could respond, she said, "Is that why you wanted me to come with you? To try to talk me into doing something? You're just a serial cheater, aren't you? You know I'll tell Jessica about this, right?"

I laughed, and when she asked what was so funny, I said, "To tell you the truth, this was Jessica's idea. She wanted me to see if I could convince you to give me a handjob or a blowjob while I drove. That's why she insisted on you riding with me."

"Oh," Hannah said, sitting back in her chair. "Why?"

"Honestly, I have no idea. I think it's because she knows how curious you are about sex and wants to do what she can to help," I explained.

"Yeah, I'm curious about sex. I've given guys plenty of handjobs; I know what I'm doing there," she said.

"Do you?" I teased her. "What about blowjobs?"

Hannah laughed and said, "Was that your attempt at getting me to give you one?"

"Maybe. Did it work?" I asked, glancing over at her with my eyebrows raised.

"Nope," Hannah said with a laugh.

"Dang. Now I have to tell your sister that I failed," I told her, getting a pity eye roll from her.

We stopped a short time later for some food and gas. As Hannah went to the bathroom, Jessica asked me, "So, any luck?"

I shook my head and said, "Nope." I recounted the conversation I had with Hannah before saying, "So, she pretty much said that she's only curious about sex because she has plenty of experience with giving guys a handjob."

"Dang. Well, keep going, if you want," she told me before Hannah rejoined us.

When we were back on the road, Hannah said, "So, did you tell Jessica that you failed?"

"Yes, I did," I said.

"And, what did she say?" Hannah asked.

"She told me I could keep trying if I wanted or just give up," I told her.

"I was thinking about it while I was in the bathroom, actually," Hannah said, looking at me. "I'm not saying that I will do it, but I'm curious what would be in it for me."

"I guess we hadn't really thought about that. You could do it for the learning experience of giving somebody a blowjob that won't finish right away," I said with a little laugh.

"It sounds to me like you just want to use me for your own satisfaction," Hannah said.

"Well, yes. But I also get satisfaction from knowing that you enjoyed yourself as well. Sometimes that can be just from a blowjob, and other times that includes a little bit more," I said.

"Like what?" Hannah asked me.

"Me playing with your body," I said.

"Oh, so now you just want to use your body?" Hannah said.

"Yes. I want to use your body to please you. I will make you moan, I will make you feel amazing, and I will make you orgasm," I told her.

"How?" Hannah asked me.

"Kissing you everywhere, sucking and licking your nipples, my hands roaming all over your body. I'll touch your vagina in many different ways, inside and out, with my fingers and with my mouth. I get way more pleasure out of what I can do to a woman than what a woman can do to me," I explained to her.

"Oh gosh," Hannah said, clearly flustered.

"Do you like the sound of that?" I asked her.

"I want it so bad," she said. "But I don't think you could do all that to me while you're driving and without Jessica's permission."

"This is true," I said.

We changed subjects as we continued to drive back home. I learned more about her, including her future plans and some more about her past, and we both shared some stories about Jessica, mostly Hannah telling me stories about her growing up.

The conversation started to die down with about an hour left in the drive. Hannah was staring out the window, and I glanced over at her. Her brown hair was pulled back into a ponytail, and her body was hidden underneath a black hoodie and blue jeans. I started to imagine what it would be like to take her virginity when she turned to me and asked, "So, if I did give you a handjob, you would still be able to drive?"

I could feel myself growing hard as soon as she mentioned it, and I said, "Yeah, definitely. It makes it harder, but I can do it."

"How would I start? Just whip it out and go for it?" She asked me.

"Pretty much. Are you thinking about it? You really don't have to if you don't want to. I would never force you to," I told her.

"I know. I just keep thinking about it, plus how big you say you are. I guess I just want to see it for myself," she said.

I looked over at her and said, "If you want to, go ahead. I won't stop you."

Out of the corner of my eye, I watched as Hannah shifted in her seat, turning to face me instead of the window. She slowly reached her hand out until it rested on my groin. Her mouth dropped a little as she felt my now rock-hard cock, and she slowly rubbed up and down my pants.

She pulled her hand away from me and asked, "If I change my mind after I start, will you be mad? What will you do?"

"I won't be mad. I just might give you my debit card as soon as we get back to my apartment and send you to get some food while I have some fun with Jessica," I explained to her.

Satisfied with my answer, Hannah moved her hands back to my groin. This time, she unbuckled them, pulled the zipper down, and moved the flaps to the side. As hard as I was, the head of my cock was already poking through the flaps, and Hannah used one of her hands to pull the flap open more while her other hand wrapped around my cock and pulled it out.

She started to slowly rub up and down my shaft, her fingers barely wrapping around the thickness of it. I looked over to see a look of concentration on her face as she jacked me off. Her eyes were intently focused on my cock, her lips pursed, and she kept a steady pace going up and down.

I kept glancing back and forth between her and the road until she finally asked, "Why do you keep looking at me?"

"Habit, I guess," I said.

"A few of the guys that I've given handjobs to asked me to take my shirt off during it. Is that what you want?" She asked me.

I laughed a little and said, "Maybe? Is that bad?"

"I don't know. Is it crazy that I've never actually let a guy see my boobs? I've only let them touch me under my shirt. And I normally stop them after a couple of minutes," she said.

"No, that's not crazy. You're smart, but a little curious. Did you enjoy it when the guys touched your boobs? What about your pussy? Did you let any of them touch that?" I asked her as her hand continued to rub me up and down.

"Yes, I enjoyed it. But I always stopped them because it started to feel too good. I have let one guy touch my vagina. He fingered me until I had an orgasm. But it was under a blanket," she told me.

"Lucky guy," I said.

"He wanted more, but I refused him. Then I ghosted him," she said. "So, can you not finish unless you see me naked? Should I just stop now?"

"No, I will still finish. It actually feels really good," I told her. I sat back a bit, lifting my arms above her as I drove. She relaxed a little too, glancing around at the road as she jacked me off. A few minutes later, she let go of me again and sat up in her seat. Thinking she was done, I went to say something but instead watched as she pulled the hoodie she was wearing up and over her head. She then surprised me by taking off her shirt, leaving her in just a black spaghetti-string tank top and what looked like a black bra.

Her hand found my cock again and resumed jacking me off. I kept glancing off, staring at her cleavage as she leaned over the center seat of the van to reach. She caught me staring and said, "Don't look too much. I don't want to crash like this. How long do we have left until we're at your apartment?"

"Probably like thirty minutes or so. Why? Are you nervous I won't be done by then?" I asked her, stealing another glimpse at her breasts.

"Maybe. I've never had a guy last this long. How are you going to clean up when you're done? Do you have a towel?" She asked me.

"I guess I was hoping you would use your mouth and just swallow it," I said with a laugh. "Umm..I think there is a napkin somewhere. If not, I'll be changing when we get to the apartment."

"Maybe we should have discussed that before," Hannah said with a laugh, her C-cup-sized breasts slightly jiggling as she laughed.

"If you do want to get me to finish before we arrive, I know a way," I said.

"That doesn't involve my mouth?" Hannah asked.

"Well, that was one option, but there is another," I answered back. She asked what it was, and I said, "Let me squeeze your breasts."

Hannah thought about it for a minute before saying, "One squeeze and make it a fast one. No lingering. And you better finish right after."

"Inside or outside your shirt?" I asked her to confirm. She told me to pick.

I took my hand off the steering wheel and moved it towards her chest. Hannah stuck it out for me as I felt her bare skin and slid down her tank top. I cupped her breast inside her bra, feeling her nipple against the palm of my hand. I could feel my orgasm coming and warned her as I gave her breast a squeeze before pulling my hand out and grabbing the steering wheel again.

I felt my body tense up, and my hips tried to lift off the seat as I started to orgasm. The first rope of cum shot out and went straight up in the air before coming down and landing next to my cock.

Hannah surprised me again by leaning under my arm and wrapping her lips around the tip of my cock. Her hand pumped my shaft up and down as more cum came out, and she swallowed it down.

When I was done and starting to go limp, Hannah took her hand and mouth off me, sat up in her seat, and licked her lips. I tucked my cock back into my boxers and put my pants back together before saying, "Wow, that was surprising."

Hannah laughed and said, "It surprised me too. At the last second, I just had an urge to do it."

"And? What did you think?" I asked her as she put her shirt and hoodie back on.

"It tastes better than I thought it would. A lot better than when I was eighteen and the guy accidentally finished on me," Hannah explained to me.

Hannah was silent for the rest of the trip and appeared to be deep in thought. I was worried that she was mad at herself for what she did, but as soon as we parked the van next to Jessica's car, she got out, walked up to her sister, and said, "I swallowed his cum. It was good." Jessica looked from me to her a few times until I shrugged my shoulders with a smile on my face.

Between the three of us, we quickly had the van unloaded. Hannah helped me return the moving van, giving me a ride back to the apartment. She stuck around for a little while longer and helped us to unpack Jessica's and Liam's belongings before giving us both hugs and saying goodbye.

Alone in our apartment for the first time, I looked at Jessica as she made a phone call. Five feet tall, her brown hair pulled into a ponytail, she was wearing a red Utah Utes shirt and black leggings that I had been checking out her ass in all day. When she got off the phone, she asked what I was staring at, and I said, "You. I can't believe we're both here, and we don't have to say goodbye or wonder when we'll see each other again."

Jessica walked over and joined me on the couch I was sitting on. She gave me a kiss and asked, "You know what I can't believe?" I asked what it was, and she responded, "I can't believe that my sister gave you a handjob and swallowed your cum."

I laughed and said, "I was surprised by both. I was convinced it wasn't going to happen." Jessica asked me to tell her all about it and I quickly did. When I was done, she said, "I bet you anything that the next time she sees me, she's going to be asking so many questions."

We had ordered a pizza to be delivered and sat around watching TV while we ate it. When we were done and all cleaned up, I helped Jessica unpack and put away more of her things, until it started to get late. We were in our bedroom, where she sat down on the bed and said, "I'm pooped."

"I bet," I replied back. It's been a long day. Bed time?"

"Almost. I just need one more thing," she said while looking at me. I asked what it was, and she said, "An orgasm. You've gotten two today. I want at least one."

I smiled as I walked over and joined her on the bed. I wrapped my arm around her waist and pulled her close to me, leaning down to kiss her. I brushed a strand of her hair away from her face as our mouths opened and our tongues joined each other.