Pretend Boyfriend

She closed her eyes and arched her back as her orgasm drew closer, her body suddenly stiffening and trembling as she came.

"Ohhhhhh fuck!" she moaned as she reached between her legs and pulled my hand against her pussy, her hips rocking to grind her pussy against my fingers as her legs trembled and shook. Long seconds passed before her body stilled and she released my hand. "Ohhh God," she moaned quietly. "Damn I needed that!"

"Yeah?"

"Oh yeah. Not as good as a cock, but I still needed it."

I nodded, looking at her big tits, unable to resist moving my hand from her crotch to one of her big soft breasts.

"You know, it'd probably be a good idea to know how big you are before my sister starts asking."

"She's going to ask that?"

"Oh hell yeah," Jen answered. "Without a doubt."

"Well, what are you suggesting?"

"It's pretty obvious you're turned on, with the size of that bulge. How about you let me see it?"

"You want to look at it?"

"Well, actually I'd like to return the favor."

"Return the favor? As in make me come too?"

She grinned at me. "If you're up to it. I wouldn't mind sucking you off. I mean just for practice. I haven't done that to a guy in a few years. And if we're going to pretend..."

"Uh huh. Just for practice," I answered. I let go of her tit and straightened in my seat. I found the little button to motor the seat back down, reclining me back until I was laying halfway down while Jen slid her seat back as far as it would go. She shifted to her knees and bent over the center console of her little car and undid the front of my pants.

"Oh fuck!" she breathed as she pulled my hard-on out of my briefs. "God Michael, I had no idea you were this big!"

"It's not all that big," I said with a shrug.

"Yeah honey, it is!" she said as she started to stroke her hand up and down me. She lowered her face to me and engulfed my engorged head with her hot mouth. I felt one of her tits rub against the back of my hand as she started to bob her head up and down on my shaft. I turned my hand over and grasped her breast, squeezing it in appreciation. Up and down she bobbed her head, sliding her lips and hand up and down my rock-hard shaft. She tried to push her face down my shaft further, driving my head into her throat for several seconds, before pulling up and gasping for breath. "Damn!"

"Oh don't stop," I groaned as she wrapped her lips around me again. "I'm so damn close."

In response, she bobbed and stroked faster, coaxing my orgasm closer and closer. I could feel my hips trying to lift off the seat towards her, powerless to stop myself as she plunged her face down my shaft over and over. "Oh fuck! Here it comes!" I cried in warning, moments before my body jerked and a huge surge of pent up cum shot into her mouth. Over and over my body jerked as I pumped more of my seed into her waiting mouth.

She slowed her strokes as my body stilled on the seat, finally pulling her mouth up and off my dick. She shifted, leaning over towards my face and pressed her lips to mine for long seconds. I could taste my own cum on her lips, but at that moment I couldn't care less. I slipped my right arm around her back and pulled her down to me making her roll in the seat until she was sitting sideways on my lap, her legs in the driver's seat. I still had my hand on her bare breast as she laid her head on my shoulder.

"This is going to be harder than I thought," she whispered.

"How so?"

"I didn't think it would be this hard to pretend."

"Seemed like you were doing a pretty good job."

"No. You don't understand. I wasn't pretending. I WANTED to do that. I WANTED to make you feel good and make you come and take your cum in my mouth. Just like right now, I want you to make my clothes fall off and have you fuck me."

"Believe me, I'm very tempted to do just that, but the side of the highway isn't quite the right place."

"It's not. But we'll be sharing a bedroom tonight. Maybe we can practice pretending then. I wanted to have my sister hear what she would think was us having sex, maybe we ought to give her the real thing?"

"I suspect that once the afterglow of our impromptu fling here fades, you may have second thoughts about it, but for now, those are pleasant thoughts," I agreed.

I spent much of the next couple hours, other than lunch, sitting with my hand on her lap, contemplating what the days ahead might bring. Lunch was pleasantly spent looking at each other across a table at Wendy's. I think we were both wondering what the other was thinking. I know I was having very conflicted thoughts, about her, about where my life was going, and even about how I felt about what we were doing. That, in itself, was difficult. Just exactly how did I feel? We'd been friends for several years. She'd been a shoulder to cry on for almost a year before I could find it in me to smile again, and then only at some silly antic of hers.

That kiss yesterday, and now today, I was attracted to her in more than just a friendly way. But her friendship was what had pulled me through the roughest of times. I didn't want to lose that. My thoughts were redirected by the sexy little grin she flashed me while clandestinely stroking one of her own nipples where only I could see.

"Penny for your naughty thoughts?"

"How do you know they were naughty?"

"Because you were staring at my tits."

"Guilty as charged," I nodded. "I was just thinking about us."

"Us? There isn't an us. Not in that way. You made it clear long ago that we were friends. That was all you wanted from me. That's why I tried to get you dating some of my friends. I wanted to see you happy again. Like you were before."

"Yeah. I know. Maybe pretending is making me think that maybe I was wrong."

"It's a hell of a time to rethink that! I mean we're about to create a massive scene in front of my whole family. That won't go over very well with anyone."

"I don't suppose it will. But that's the plan, isn't it?"

"It is. Maybe we better call this off. We can turn around and I can just tell everyone I got sick."

"That doesn't solve the longer-term issue, does it?"

"Not really, but then this really isn't your problem. It's mine. I made this mess. This was a bad idea. No. It was a stupid idea. I shouldn't have dragged you into it. We'll head home," she said standing up. "It was kind of fun pretending though."

I got up and followed her to the car. "Maybe I should drive for a while?"

"Sure," she agreed, tossing me the keys. Minutes later I pulled onto the interstate.

"This is the wrong way. Home is south!"

"Yep, it is," I answered with a shrug.

"We're not going home, are we?"

"Not yet," I answered.

"You're going ahead with this anyway?"

"That's what friends are for, right? Besides I'm not done having fun pretending."

She unbuckled her seat belt, rolled to her knees and leaned to kiss me on the cheek. "I'm glad."

Another two hours had us at her parent's house, if you could call it that. It was more like a massive two-story log cabin. There were several cars parked in front of the large structure. I climbed out of the car as Jen walked around it to me. "You ready?"

"Is it too late to change my mind?"

She leaned against me, kissed me on the cheek and whispered in my ear, "Wanna know a secret? I sleep nude. Think about that!" I looked at her in surprise. "Uh huh. Makes sharing a bedroom more interesting, doesn't it?"

"It does that."

"Still wanna change your mind?"

"Maybe not so much," I chuckled.

The next hour was probably the most uncomfortable of my life. Every member of the family wanted to know all about me and how I met Jen and every detail of my life. The most critical though were her dad, to be expected, and her older sister Sue, who clearly didn't expect me to be real.

Dinner was a fish fry, which was apparently a family tradition, with fish caught right out in the umpteen thousand acres of water the cabin was built on. Fortunately, I like fish and was able to avoid conversation somewhat by keeping a mouth full of food.

"Done eating?" Sue asked as dinner wound down.

"Um. Yeah."

"Good! Let's go for a walk!" she said, looping her arm in mine and turning me away from the house and the picnic table I'd just eaten at. She led me off towards a trail in the woods that followed the winding shoreline. "So. My sister seems taken with you."

"Seems that way," I agreed.

"So, just what are your intentions towards my sister?" she asked as the trees closed off the view of the house.

"We'll, that's kind of up in the air."

"Oh? You're not the fuck 'em and leave 'em kind, are you?"

"Not that I'm aware of."

"So, you're going to make an honest woman of her?"

"When the time's right."

"And when exactly is that?"

I looked at her with surprise. "I think that's between her and me."

"But not soon?"

"Maybe, maybe not."

"That's evasive."

"It is, isn't it?"

We stepped into a little clearing along the shoreline a few moments later. She let go of my arm and stopped on the small sandy spot. "Wanna swim?"

"Um, I don't have a suit."

"So? Neither do I," she said as she started pulling off the little dress she had on. Her lacy bra went next, exposing a pair of tits almost as big as Jen's. I was still staring at her naked chest as she bent over to push her bikini panties down and step out of them. "Well?"

"Well what?"

"You gonna get naked and come with me?"

"You don't think your husband will mind?"

"I don't care if he minds or not. This isn't about him, it's about you!" she said as she stepped closer to me and started undoing my shorts.

"I'm still not sure this is appropriate."

"Not into swimming? Then fuck me," she said as she pushed my shorts down despite my attempts to prevent it. Her hands were on my briefs as soon as my shorts were sliding down my legs, pushing them down and grabbing my hard-on. "Ohhhhh. Now that is a dangerous tool. I hope you know how to use it safely!"

"I'm pretty sure I do."

"Oh? Then show me. My pussy is wet, your cock is hard, I say we have a little fun."

"You know, if this is to see if I'll cheat on Jen, you're barking up the wrong tree."

"And just what tree should I be barking up?"

"If I'm sticking it anywhere, it's in Jen, not you."

"You're sure about that?" she asked, pushing my dick down and stepping towards me, so that my rock-hard shaft slipped between her thighs, her hot pussy rubbing against my shaft. She pressed her chest to my still shirt covered chest and rocked her hips to drag her pussy along my dick. I could feel her wet lips spread and partly wrap around my shaft, my mushroom head slipping between those hot soft lips with each stroke. "All you have to do is say yes, and my hot sexy pussy is all yours. How about it stud? Fuck my hot little cunt! Just push it right in. Let me feel this big fat shaft slide right into me."

"Not happening," I whispered.

I felt her fingers stroke the bottom of my shaft, her hand under her own butt, pushing me up between her lips. I could feel the entrance to her depths with my head. All I had to do was let her keep doing what she was doing. It felt like each stroke she made put me closer and closer to slipping inside her.

I closed my eyes for a moment and then reached for her hips. I pushed her back, pulling my dick from between her thighs. "Sue. No!"

It took a moment to get my briefs back up from my thighs and then I pulled my shorts up. "I think I better go back to the house," I said as I turned away and headed back down the trail, leaving her standing naked behind me.

"Hey! Where did you disappear to?" Jen asked as I walked back into the house.

"Your sister took me for a walk in the woods."

"Uh oh."

"Uh huh. Uh oh. She's not only not convinced that I'm the real deal, she stripped and tried to fuck me or more correctly tried to get me to fuck her."

"Did you? Fuck her?"

"No. She got my dick between her thighs before I put a halt to her plans. "

"Damn! Lucky girl. That's closer than I've gotten," she said with a grin. "You better fucking well put that thing in ME tonight!"

"Are you kidding? I'm about ready to make those clothes fall off and do it right here!"

Jen squeezed me and giggled. "If you wanna show off, we can go on the boat dock, and you can stick it between MY thighs. Or WE can take a walk in the woods."

"Why not? The woods sound good to me, as long as you promise to get all the way naked for me."

Jen smiled at me and stepped away, pulling me by the hand out of the house. We practically ran together towards the little trail her sister had taken me down. In only a few short minutes we were standing in the same place Sue, and I had been, slowly undressing each other. I'd already seen her tits, but she did hold one surprise yet, her now completely shaved pussy and mound.

"God you're beautiful," I whispered to her as I stepped to her. "I think your sister is spying on us."

"Yeah? Well, we better make it look good then!"

I grinned and took her in my arms kissing her like I'd done the day before. By the time we'd shared several minutes of the embrace my dick was between her thighs, the two of us rocking in time with each other. I felt my cock sliding between her soft wet lips, my head completely covered at the end of each stroke. I lifted one of her legs and reached down under her butt to push my head up with my fingertips. I felt her freeze as I let my head slide between her lips and press the very tip of my head into her entrance. "God, I want this," I whispered as I held my head at her entrance.

"Michael, I've fantasized about this for two years," she whispered back. "Take me and make me yours," she whispered back loud enough for only me to hear.

I pressed up, forcing my head against her vaginal opening, coaxing her body to expand and accept me. Slowly I began to slide into her, my already lubricated shaft slowly sliding deeper and deeper into her. She let out a soft moan before pressing her lips urgently back to mine. I held her tightly to me, her nipples pressing into my chest like two hard marbles. Very slowly I started to push in and out of her, keeping our kiss going as I pushed deeply into her vagina. In and out I slid, her hips already trying to rock in time with mine after having already teased her clit for so long.

"Oh fuck! Gonna come Michael!" she groaned as she broke the long kiss.

"Me too," I grunted in response as her pussy started to clench and spasm around me. I held her close, continuing to stroke in and out of her hot wet depths, the urgency building in me by the second.

"Not in me. I'm not on anything. Just pull it out, please!" she begged.

"Oh fuck!" I grunted as I pulled my engorged cock from within her, moments before my body jerked. I felt a surge of cum flow up the length of my rock-hard shaft and then squirt out onto her body and mine. Over and over I jerked, pumping shot after shot of hot cum on to her sexy body.

"Ohhhhhhhh fuck!" she moaned as her arms pulled me tighter to her as her own climax did its thing within her. "God, I wish that was inside me," she whispered as her climax slowly faded.

We stood holding each other, kissing softly until my softening cock slipped from between us. "I think we ought to get dressed and head back, before someone comes looking for us?"

"Your sister already did."

"I was thinking my mom, actually," she said. "I'm not sure you want her finding us like this."

"No? She prudish or something."

"Not exactly."

"Then what exactly?" I asked curiously.

"Let's just say that if you were shocked by my sister, you're gonna love mom."

"Are you saying she'd."

"Try to fuck you? I've only brought one potential boyfriend home, and that's what happened. Most guys don't think it's appropriate for their future mother-in-law to be trying to fuck them."

"Good Lord," I answered, shaking my head. "Wait! You expected this!" I said, looking down at her as she bit her lower lip.

"I did," she admitted quietly. "Remember me saying we'd have a fight? Well, this is what I expected would be what we'd use to start that fight."

"So, what? We just wait for her to put the moves on me and then we have a big fight?"

"Something like that," she said with a shrug.

"What happens if I don't want to have a fight?"

"But that was the plan, right? We'd have a fight and break up. Remember?"

"Yeah. I remember. It's just that, well, I'm kind of enjoying pretending with you. Kind of wondering if maybe we aren't really pretending all that much."

"Are you saying," she asked in a whisper, leaving the question unfinished.

"I'm saying that maybe I might not want to keep pretending."

"You want to call it all off?"

"No. I'm saying that I might not want to have that fight."

She looked at me for long seconds. "Michael, playing at pretending like this and actually feeling for real. They're two different things. I care about you, a lot, but are you really ready for that? Ready for. me? I mean this is fun. I love feeling what you do to me, but for real?"

"I don't know. But I'm not sure I want to kill the possibility, and that's what's going to happen is we have that fight."

"It would."

"Then maybe I'm not ready to have that fight."

"Jesus Michael! I'm not saying I don't want to make it real, but are you sure?"

"No. I'm not sure of anything at the moment."

She nodded and pushed away from me. "Let's get dressed. It's getting dark."

We didn't talk all the way back to the house, ducking in away from the swarms of mosquitos that were coming out. It seemed like everyone was gathered in the main room; her mom Trina, and her dad Don, as well as her sister and her husband. There was another young woman there, maybe late twenties that had to be the younger sister Karen.

"You two have a nice walk?" her mom asked.

"We did!" Jen answered with a smile.

"I bet," her little sister answered. "By the way, your shirt is on inside out."

Jen looked down at herself and practically ran from the room blushing.

"Oops," I said quietly. "Guess that wasn't such a good idea."

"Oh. Fucking in the bushes is a fine idea. I wouldn't mind trying you out like that. But if you want to keep it a secret, well you either gotta go naked or make sure everything is put back on right. Personally, I'd go for the naked route!" Sue said with a devious grin.

"Jesus Sue!" her mom said. "Does everything revolve around sex for you?"

"Is there anything better?" she answered her mom.

Jen's mom patted the sofa next to her. "Come on Michael. Come sit."

"Sure," I answered with a shrug, stepping over and sitting down between her and her youngest daughter.

"So, what do you like to do in your spare time?" Trina, her mom, asked me.

"Besides fuck my sister?" Sue added from where she sat in a chair not far away.

"Read, write. Watch old movies," I answered with a shrug.

"You write?" her mom asked curiously.

"Yeah. Science fiction mostly."

"Oh? Tell us!" her mom coaxed, twisting in her seat slightly, her leg now pressing against mine. I tried to move my leg away while I explained about my books, but hers followed and I soon had one of her hands resting on my bare thigh. Uncomfortable would be an understatement. Not that she wasn't still very good looking for her age, or that her selection of evening attire didn't show a surprising amount of skin, or that her nipples poking out the thin shirt wasn't provocative, but with her husband sitting in his recliner only a dozen feet away, the last thing I wanted to do was anything inappropriate. When Jen had come back, she settled in a chair half-way across the room, watching me, trapped between her mom and younger sister. I wondered if she was going to start that fight when her mom reached for my hand and slowly pulled it into her lap. I couldn't see much, but my fingers told the story of baggy legged shorts and missing underwear. Twice I slipped my hand out of her crotch when she let go of it, only to have her find my hand again.