Pretend Boyfriend

I was glad it was Friday. It was going to be a wonderfully long relaxing nine days. Two weekends, four vacation days and the 4th itself. Not many vacation days to get such a long July break. I planned on doing some fishing and relaxing. Maybe I'd go camping a few days. Anything that keeps me away from work to unwind.

I was surprised to see Jen standing on the top of the ladder in front of her house across the street, trying to replace a bulb on the security light. Jen is about my age, her 32-year-old body is an incredibly sexy and curvy size ten. Not thin, but so damn sexy just the same. Five and a half foot tall, brown hair, green eyes, 40D boobs and a good-looking ass. I'd seen her in bikinis dozens of times in the last three years that we'd known each other. If she wasn't such a good friend, and helped me along after I lost my wife, I might even think of trying again with her. But the reality is she knows just how hard it was for me and knows that my heart is still with Angie, even though she's gone. So, it'd never work. She'd always wonder if I was thinking of her or Angie.

"What are you doing up there?" I asked as I walked up to the ladder and looked up at her, realizing suddenly I could see right up the little dress she had on, all the way to the tiny white thong panty. "I thought you'd be packing," I said as I looked back down, feeling embarrassed as she looked down at me.

"I'm not going," she answered, going back to work on the light.

"Not going? It's like a family reunion. How can you not go?" I asked in surprise, looking back up at her.

"Because my sister decided to come," she answered with a shrug,

"That's great!"

"NO! It's terrible!" she said, looking down at me with a scowl.

"It is?" I asked confused. I was sure my face showed just how confused I was.

She stood on the ladder, twisted around to see me, looking down at me. "Yeah. I can't go now!"

"Why not?" I asked, my confusion clearly not dispelled.

"Because," she said, turning back to face the ladder and bending slightly to step down the ladder towards me. I couldn't help but see that bare ass even better as she did, "I got tired of her badgering me about getting married. "

"So?"

"So, I told her I was seeing someone."

"Okay. Little white lie. No big problem."

"That was months ago. She kept wanting more. So, I told her he was tall. Six two to be exact. Hot, hunky, handsome, my age, sandy blond hair and beautiful blue eyes."

"Sounds like your perfect guy. Besides all the hot hunky stuff, it sounds like you're describing," I was saying before she interrupted me.

"You. Yeah. I needed a description and I just blurted it out. Now she thinks I'm seeing you and you're going to pop the question any day now," she said, cringing at the expected response.

"Say what?" I squeaked. "Pop the question? As get engaged?"

"Yeah. God I'm sorry! It kind of got a life of its own. But you see, if she comes, I can't go! She'll know I was faking the whole thing and blab it to everyone!"

"Like they won't know now? I'm mean she's bound to have told your mom. And she's sure to have told everyone else," I said, still a little shocked.

"Oh God. You're right. Now I really can't go. Not ever."

"Boy, when you dig a hole, you dig a deep one," I chuckled. "You're just going to have to tell your sister that you broke up or something."

"I can't. She'll think I made it all up!"

"You did."

"But she can't know that!"

"Well. I don't see any way around it," I said with a shrug.

"Me neither. Unless," she paused mid-sentence and I looked at her for long seconds, waiting. "You know. Maybe there is a way."

"Yeah?"

"Uh huh. What if, well, what if you went with me?"

"Huh?"

"Go with me. Pretend you ARE my boyfriend."

"Wait? What? How does that help?"

"Well, I know, we could have a big fight and break up and then that'd fix everything!"

"Except your family will hate me," I said with a frown.

"I'm not worried about that. I can straighten that all out some day when I find a real boyfriend."

"Like that's going to happen any time soon. That's why you want to try this crazy idea, because you haven't found anything you really like in a guy."

"That's not true. I like a lot in you!"

"Yeah. But we're friends, not boyfriend girlfriend."

"Well. Yeah. But still. You're going to help me out on this, aren't you?"

"It's nuts!"

"So? What were you going to do with vacation anyway? Go fish a few days? You can do that there."

"I was going to RELAX!"

"And you can't relax there?"

"With everyone watching my every move and evaluating me? THAT is not relaxation! Besides, we could never pass as lovers. Hell, we haven't even ever kissed each other, let alone shared a bedroom."

"But you know everything about me, and I know about you. All we have to really fake is the intimate stuff. You can't tell me you wouldn't like to see me naked, right?"

"Fake the intimate stuff? Really? You want to just fake hugging and kissing and snuggling in front of everyone? Like your sister isn't going to see through that?"

"Well...we'll just have to fake it good. We can do that. I'll show you. Kiss me."

"Huh?"

"Kiss me. You don't want to get all the way there and never have tried kissing me, right?"

"Out here?"

"Might as well. I mean we're gonna have to do it in front of my family."

"Wait! I haven't agreed to anything!"

"You will. You always do."

"I do? Really?"

"Uh huh."

"What about Gina? Um, Tammy? Let's see. Amanda? How many other friends of yours did you try to set me up with?"

"Okay. So maybe dating wasn't something you agreed to. But pretty much everything else you've done."

"Everything else was a reasonable request. I'm not so sure this is."

"Maybe it isn't. But you will anyway, right?" she asked hopefully.

I looked at her with a frown for long seconds. "All I have to do is pretend to be your boyfriend for a couple days?"

"Yep. Just pretend a little. Give me a few hugs and kisses in public. It'll be easy!"

"That's all? A few hugs and kisses. Like that's all it's really going to take? I think you're crazy!"

"Of course I'm crazy. But I know you'll do it, because I'm asking you really, really nicely," she said with a wide grin.

"Uh huh. And what about sharing a bedroom and little things like trying to show that we're two lovers? You really want me running my hands all over you? I mean that's what a guy in love does. Grabs your butt or your tits when he thinks no one is watching. That's really what you want me doing?"

"Well, I'm sure we can manage to share a bed. We're big boys and girls, and I'm sure I won't mind too much if you maybe grabbed my butt or boob once in a while. Just for pretend of course."

"Just for pretend. Yeah, how do I pretend to squeeze your sexy ass?"

"You think my ass is sexy?"

"Of course I think your ass is sexy. But that isn't the issue. You're my friend. I shouldn't be grabbing anything, butt or boob or anything else."

"You really think my butt is sexy?" she asked again.

I rolled my eyes and shook my head. "Yes. If you really wanna know, yes. I think your butt is sexy, as is everything else about your body, at least the parts I've seen. There! I said it. Happy now?"

"Yep. Now kiss me," she said with a huge smile, stepping the remaining half step towards me, her arms reaching up to circle my neck. "And if you happen to squeeze my butt, I guess I wouldn't mind too much," she whispered as I let my arms slip around her, pulling her gently towards me. I let my arms rest around her waist and leaned my face down and gave her a short soft kiss. "You're right. No one will believe we're lovers if you kiss me like that. Is that the best you can do?"

"What? Not a good enough kiss?"

"Michael, I've seen how you kissed Angie. How you held her, how you squeezed her to you, how your hands used to hold her to you. Those kisses dripped 'I love you'. What you just did was a ho-hum kiss."

"What? You want a curl your toes, make your clothes fall off, wanna get fucked kiss?"

"Is that how you kissed her?"

"Her?"

"Angie."

"No. This is," I answered, sliding one hand up to the middle of her back to pull her tightly to me, the other sliding down to the round of her butt. I pressed my lips gently to hers, letting my tongue tease across our joined lips until hers parted and let my tongue tease hers. My arm held her tightly to me, her hardening nipples evident against my chest even through her bra and dress. My other hand slid down to the hem of the short dress and pulled the back up, sliding my hand up her bare skin until I could cup her bare ass cheek the tiny thong underwear left exposed. For long seconds we kissed, her body melting into me as we sucked and teased each other's lips, my hand massaging her bare ass cheek and my fingers slowly working between her legs until the tips of my fingers rubbed gently against the narrow strap sliding up between those smooth round cheeks.

"Holy fuck!" she whispered breathlessly, her lips only millimeters from mine as we broke the kiss.

"Sorry. Kind of got carried away," I breathed, slipping my hand from under her dress and moving it back to her back, still not letting up the pressure of my other arm holding us together. I could feel her hard nipples moving against my chest as we both panted for breath, her pelvis pushing against mine, my suddenly growing hard-on obvious to both of us.

"What's to apologize for? I asked for a kiss and God did you give me one. What was it you called it? A make my clothes fall off and want to be fucked kiss? Jesus. That's a pretty damn good description. My pussy feels like a waterfall right now. So, you're going to have to either take me into the house and fuck me or let me go in and fuck myself."

"Sorry. I guess I haven't kissed anyone in a while, and you wanted it to be good."

"Trust me! It was! You kiss me like that in front of my sister and she won't have any doubts."

"Yeah. About that. You sure this is a good idea? I mean fooling your family like this?"

"Michael, after a kiss like that, I'd be a fool to pass up the chance to get kissed by you again."

"It was that good of a kiss?"

She pulled away slightly and slid one hand down from my neck and down my arm. She drew my right hand from her back around between us and then pushed it down. She pressed my hand down below her skirt and then back up again, pressing my fingers against the crotch of the tiny thong panty. "Feel how wet I am and then see if you still need to ask that question."

I let my fingers stroke her through the material of panty, feeling both the wetness of the material and the softness of the pussy it covered. It'd been over three years since I'd felt a woman in my arms, or had my hand between her legs, and my lower head insisted that I let my fingers linger there, rubbing and stroking her softness much longer than my higher brain knew was appropriate. "Yeah, you are a little wet," I finally said as I drew my fingers from between her legs. "This isn't going to be a problem, is it? Not going to mess up our friendship?"

"It might change that relationship a bit," she whispered. "But I think we can weather it. I mean, it's only a few days of pretending, right? I mean we're just pretending to be lovers. We don't actually need to go that far, unless of course you want to. I mean, we don't have to. But if you wanted to, I suppose we could. Just to keep up appearances. It'd be hard to deny if sounds of fucking just happened to come from our bedroom. Not that we'd HAVE to have sex. We could just pretend to."

"Yeah. We could pretend to," I agreed, suddenly thinking that maybe pretending to be lovers was going to be a lot harder than she was suggesting.

"Why don't you go pack some clothes, and I'm going to go in and pack. We can come in the morning, I mean you come over in the morning and we can take my car. Okay?"

"Yeah," I agreed as she pushed away, but not so far away that if I wanted to I couldn't just reach out and pull us together again. I took a deep breath and stepped back further.

It was Saturday morning. To say I was full of trepidation would be the understatement of the month. I'd had a long night to think about this hairbrained idea as well as the very intimate embrace I'd shared with Jen. I'd let things get very out of hand. True, she was a very good-looking woman, and the conversation had seriously aroused me, but I still should have controlled myself. I wasn't looking for a replacement as I'd told her every time she tried to set me up with one of her friends. I'd broken down on two occasions and agreed to go out with her offerings, but neither was going anywhere. Not because they didn't look good, or because they weren't provocative or even because they weren't sweet young women. No, the problem was that I just had a hard time feeling comfortable with some other woman in my arms, let alone my bed. Maybe that's why yesterday bothered me so much. When I kissed her, I WAS comfortable. I WAS aroused and I enjoyed the hell out of both the kiss and the reaction. And maybe even more importantly, because I walked away wanting to kiss her again and take her clothes off. I wanted to see what her bikinis hid from me. I wanted to take her to bed. And that scared me. It's only been three years. Barely a drop in the time bucket. I didn't want to lose those memories of things that I shared with Angie, things I hadn't shared with any other woman, ever.

"All set?" Jen asked as she walked out the front door of her house. I hadn't even realized I'd walked across the street and was standing in her driveway by the car.

"You sure this is a good idea?" I asked as I looked down at her, the short yellow sleeveless sun dress molding itself to her sexy curves. I could feel my dick start to harden in my shorts as my body remembered how she felt against me the day before.

"I think it's a terrible idea, but it's the only one I have," she said as she stopped less than a foot in front of me. "You going to kiss me? I don't mean like yesterday, but a nice sweet 'I love you kiss'?"

"Do I need to?"

"I think we need the practice, if we're going to pull this off."

I nodded and reached out to her waist and slipped my arm around her and pulled her to me. I lowered my head and softly kissed her for several short seconds. "Better?"

"Yeah," she said a little breathlessly. "That'll do. You can throw your bag in the trunk."

"Sure," I answered, finally letting my arm release her from against me. I turned and rolled my suitcase to the back of the car and hefted it into the trunk, closing the lid. I walked to the passenger side and slid into the bucket seat while she started the car. I couldn't help but think how sexy she looked in the short dress, which almost immediately led to wondering if she again wore a pair of thong underwear. This was going to be a lot harder than I thought. We weren't even out of the driveway, and I was thinking inappropriate things. How the hell were we going to share a bedroom?

"We'll manage," she said as she looked over at me. "And yes. Yellow to match my dress."

"Huh?"

"You asked if I was wearing a thong again and how we were going to share a bedroom if you were already thinking about me naked."

"I asked that?" I said in shock. "Out loud?"

"Not overly out loud, but enough for me to hear," she answered with a grin. "You frequently do that, mumble what you're thinking. Didn't you know that?"

"Ummm. No. I didn't. No one has ever told me that before."

"Well, maybe it's just me then. But you better be careful what you mumble in front of my parents. They may not understand."

"Yeah. I guess I better," I agreed.

We were probably half an hour into the nearly six hour drive before either of us spoke again. "You know," she said softly, "most guys like to touch their girlfriends."

"Huh?" I asked, drawn out of the thoughts I was lost in.

"I said most guys like to touch their girlfriends. It seems to me you might need some practice."

"I do?"

"If you have to ask, yes, you do," she answered, reaching over with her right hand to find my left and pull it to her. She placed my hand on her bare thigh. "If we want them to think we're lovers, you need to get used to touching me."

I let my fingers slowly stroke up and down the inside of her thigh, my fingertips just teasing the soft creamy skin. "You're sure you don't mind me touching you like this?"

"Trust me, I don't mind at all. You have my permission to touch anyplace you want. If you'd have touched Angie that way, you should probably figure on touching me that way too."

"You're sure that's what you want?"

"If we're going to pretend, we need to pretend all the way. I promise, I won't get mad or hold it against you after this is over. So go ahead. I know what you're thinking. I won't stop you."

Maybe she did know what I was thinking. I let my stroking fingers begin to slowly work up her thigh towards her crotch, the short yellow skirt material pushed up, millimeter by millimeter. I let my fingers tease her bare skin, stroking my fingertips in small, slow gentle circles until I could feel the smooth slick material covering her pussy. I let my pinky start to stroke up and down the crotch of her panty, gently teasing what was hidden beneath.

She held both hands on the steering wheel, staring out at the road, but I could see her breathing deepen as my teasing fingers gently aroused her. Without looking over at her, I let my pinky worm its way beneath the thin panty material until my finger was stroking up and down over her wet pussy lips. Her inner labia spread and allowed my finger to slip between them, my finger now rubbing up and down across her hard clit hidden between them.

I was a little surprised when she put on the turn signal and exited the interstate, so I pulled my hand from between her legs.

"Don't you dare stop that," she hissed as she pulled the car onto the shoulder of the exit ramp. "We may only be pretending to be lovers, but there's nothing pretend about my body and what you're doing to it again," she said as she looked over at me. She put the car in park and then spread her legs as far apart as the confines of the car would allow.

"So, you want me to keep going?"

"I think that's about the stupidest question you've ever asked me," she said as unbuckled her seat belt, shifted in her seat and then lifted her butt off the seat as she pulled her skirt up nearly to her waist. She reached for the strings of her panty and pulled them down, sliding the tiny bit of material down her thighs. She lifted each leg in turn until she had the panties completely off. She lifted herself on the seat again, pulling the skirt up in back so she was no longer sitting on it. She settled back on the seat, her skirt now bunched around her waist and spread her legs again. "You're going to see it sooner or later, so we might as well make this easy for you."

"Make it easy for me?"

"To play with my pussy. There's no way I'm driving another five hours all teased and turned on like this. You got me turned on, you need to finish the job," she said as she reached over to pull my hand back between her legs.

I nodded and let my pinky start to stroke up and down her slit again, rubbing up and down over her hard excited clit. She reached up with one hand behind her neck and untied the little string that held the top of the dress from falling down off her big soft tits. She pulled the top of the dress down, exposing a tan colored strapless bra. It only took a moment for her to pull the front of the bra down and completely expose her tits to me for the first time. I was a little surprised to see a small silver barbell shape poked through each big hard nipple. I continued stroking her clit while she used her hands to pull and tug each nipple, using the little barbells as handles to tug and twist them.