Friends With Extra Benefits

by Luke Young

  Switching to her messaging screen, she sent Jim a text, asking what he was doing and telling him she missed him.

  Caroline glanced up at the professor and pretended to listen as she waited for Jim’s reply. After a few minutes and no response, she sent another text, this one detailing exactly what she wanted to be doing with him right at that moment. Closing her eyes, she began to fantasize about her steamy message while she unconsciously and slowly ground her hips into the chair. After a few minutes, she pulled herself back to reality and glanced around the room to be sure no one was staring at her.

  Finding no one the wiser, she sat up straight and let out a long, slow breath. With a naughty fire in her eyes, she sent one last graphically explicit message about what she was going to do to him when she returned to the apartment in just ten short minutes. He was instructed to be ready.

  In the apartment they shared, Jim was wearing only a towel as he sat on the sofa, wearing a big smile in the midst of a phone conversation with Victoria. She had just finished telling him all about the trick she and Jillian were planning to play on Brian. He couldn’t believe his brother was actually falling for it, and he promised not to give it away if they spoke. Next they discussed the recent checkup with her OB GYN and how both baby and mother were doing fine. Jim had ignored the three beeps he received for new text messages, as he was engrossed in Victoria’s captivating story.

  After sharing what he and Caroline were up to lately, Victoria started telling him about her experience with the two lacrosse players in the bar and her attempt to help Lisa lose her virginity. It was at this time that Caroline strolled through the door.

  Taking in the vision of Jim sitting on the sofa wearing only a towel, she grinned, thinking he got her messages and that he had cleaned himself up properly in order to experience the pleasure she’d spelled out in her final text. Upon hearing him laugh out loud, she glanced up to his ear, saw he was on the phone, and frowned a bit. He smiled at her with a quick motion that indicted to give him a minute, and Caroline slumped down in a chair, tossing her backpack beside her.

  Jim widened his eyes as he said, “Oh, Victoria. No, you—”

  “Is everything okay?” Caroline asked, concerned.

  He ignored her as he listened intently. Caroline moved to the edge of her seat.

  Jim asked, “What the hell were you doing in the men’s bathroom?”

  After listening, he shook his head with his jaw gaping. Caroline stared at him now, both confused and worried.

  “What’s going on? Is she okay? Is the baby okay?”

  “He said what…? No…. Okay, yeah.” Keeping the phone to his ear, he looked at Caroline with a dizzied expression and said softly, “She put me on hold for a second. Her tea water is boiling or… Sorry, I’m almost done. She’s in the middle of this story.”

  “Is everything okay with the baby?” Caroline asked.

  “Oh, yeah.”

  “And she’s fine, too?”

  “Sure.”

  “Thank God.”

  “She’s just telling me all these stories about—” Jim held his finger up to her once more as Victoria returned to the phone. Caroline exhaled deeply before slumping back into the chair.

  He giggled as he listened intently. Caroline stared out the window at nothing in particular as her frustration grew.

  “No way! The police… Sure, I remember Officer Williams.”

  Caroline frowned. She stared at Jim as he glanced back at her with a look that screamed he wanted to tell her all about this. At that moment, she couldn’t care less.

  Moving to the edge of her seat, she whispered, “Did you get my texts?”

  He narrowed his eyes at her, and she repeated the question.

  “Hold on a second,” Jim said into the phone before pulling it away and covering it with his hand. Giving Caroline his complete attention, he asked, “What?”

  “You didn’t get my text messages, did you?”

  “No, sorry. I heard the beeps, but I’ve been so… Sorry. I swear, I’m almost done. Two minutes.”

  “Sure.”

  Jim put the phone back to his ear. “I’m back.”

  After listening a moment, he chuckled then asked, “They were both naked?”

  With her jealously slowly boiling over, Caroline rose from the chair and walked to him while wearing a sexy expression. Slipping to her knees in front of him, she placed her hands on his towel, and Jim looked at her, surprised.

  “They didn’t take them to jail, did they?” Jim asked.

  Caroline pulled the towel open and gazed down at his manhood lying there sparkling clean and flaccid against his thigh. She licked her lips, grinned and then plunged her head down.

  With his eyes widened and his jaw slackened, Jim stared down at her in disbelief.

  “Uh-huh,” he muttered into the phone. “What was that?”

  His eyes locked on Caroline’s head as she worked her magic over his quickly responding penis. “Oh, yeah. That’s really, uh, crazy stuff.”

  Caroline slipped a finger under a particularly sensitive area and Jim cried out, “Caroline!”

  Startled, his eyes opened wide. “Um, yes, she just walked in… um, okay hold on.”

  He covered the phone with his hand, swallowed hard, and then said, “She wants to speak with you.”

  Titling her head up with her mouth still occupied, her eyes met his. She shook her head slightly no, and he stared down, mesmerized at the sight of her enthusiastically doing what she was doing.

  Caroline quickly plunged her head down, taking more of him unto her mouth and leaving him struggling to breathe. He looked at the phone, confused, then placed it back to his ear. “Uh, she can’t talk right now, she’s… Actually, I kinda really need to go. I have this thing that, uh…. Okay…. Bye.”

  Abruptly, he ended the call and stared down at her dreamily. A few minutes later, when she had finished him off, her eyes traveled up to his face. “You really shouldn’t ignore my texts.”

  He nodded quickly in wholehearted agreement as he struggled to catch his breath.

  12

  The next day in Miami, Jillian and Brian spent the day at home, poring over the final details of Operation Erection Shield. At 3:00 p.m. they headed up to the bedroom for some last-minute preparations, as in, repeated sex, designed to render Brian’s penis un-erectable. Then at 3:52 p.m., Jillian gave him one last preparation as he stood with his back pressed against the front door. Brian held on for dear life with his mouth wide open, letting out a silent scream as Jillian brought him to orgasm, albeit a small and mostly painfully strained one, for the fifth time inside of an hour. He was literally and figuratively spent.

  She stood and wiped her lips as he zipped up while panting like he’d just completed a marathon. Jillian opened her mouth wide and shifted her jaw from side to side to work out a kink before she glanced up at him and smiled. “That should do it.”

  Squeezing his groin suggestively, he gave her a sexy smile. “I don’t know. I might need just one more.”

  She simply shook her head ruefully and scoffed.

  “I’m kidding.”

  “Just get the heck out of here.”

  Brian opened the door and stumbled out. On the porch, he wobbled a little before turning back to her. “I’m dizzy.” He shook his head and widened his eyes as he clutched his chest.

  Jillian frowned. “Geez, you guys complain that you don’t get enough sex, and then when you do you—”

  “I’m not complaining. I just probably should have made sure my will was in order before we did all that. If I go down during the walk over there, just remember I love you.”

  “I love you, too. Now go, or you’re going to be late.”

  Moving to her, he gave her a kiss.

  She asked, “You have the pill?”

  He patted his pants pocket and then smiled. “I do.”

  “Good luck.”

  He turned and headed down the path toward the street, weaving a little. A
bit concerned, she watched him and called out, “Be careful crossing the street.”

  Ten minutes later, Brian was fully nude and sitting over a towel on a chair in Victoria’s bedroom with a completely flaccid penis. He was working it and working it without result as she prepared the kit in the bathroom.

  Victoria poked her head through the doorway. “Ready?”

  “Not yet.”

  She narrowed her eyes as she failed to see what she was expecting and checked her watch. “Hurry up.”

  Victoria disappeared into the bathroom for thirty seconds then rushed out and asked, “Anything yet?”

  “No, I’m sorry. I don’t know what—”

  Storming over to him, she got down on her knees. She stared down at his pathetically unresponsive, shrunken penis and lightly tapped it with the back of her hand. “What the hell is wrong with you?”

  “I don’t know. Maybe we could try it another time.”

  Victoria stood and rubbed her chin. “No, it’s got to be today, or it won’t be ready for her birthday party next week.”

  “Why not? It only needs, like, two days to set up right?”

  “Um…” She stammered as the gears in her head turned. “That’s right, but I’m completely slammed the next few days with school and just everything that—”

  “Okay, okay,” he interrupted while fighting back a grin.

  “Wait. I think I have something that might help.”

  She rushed over to her night table, opened the drawer, and began pulling out various sex paraphernalia. He grinned and nearly broke into laughter while he stared at her back as she pulled out items one by one: a dildo, handcuffs, condoms, another dildo, and then, finally, a spray bottle. “Okay, here it is. Wait, no… this is desensitizing spray. You definitely don’t need that.”

  When she returned her attention to him, his smile morphed into a frown, and he began pulling on his penis again.

  “I think, uh, I felt something.” He glanced up at her and nodded. “Yeah, maybe.”

  “Really?” she asked hopefully.

  “Yeah, I think it’s starting to happen.”

  She took a few steps toward him and glanced down at it with her eyes narrowed. “It looks the same to me.”

  “No, I felt it… really.”

  She widened her eyes. “Why don’t you just take the Viagra?”

  He shook his head. “No way. Last time I nearly ended up in the hospital. Do you know they need to stick a needle in your penis to drain the blood when that happens? I’m not having a needle shoved into it. No way!”

  “Oh, you big baby.”

  Victoria frowned as she stared down at him. Brian kept jerking his completely flaccid and thoroughly overworked penis. He was pretty sure that Jillian’s repeated attention made it virtually impossible for him to attain another erection for hours, possibly days.

  She glanced at her watch before staring back down at his manhood and shaking her head in frustration. “Pathetic.” She widened her eyes. “You had sex today, didn’t you? I told you not to.”

  “No, I swear.”

  She gave him a skeptical look. “When’s the last time you did it then?”

  “Like three days ago. I’m just nervous. Maybe because I almost hurt myself last time.”

  “I told you, this is a new kit. They assured me—”

  “Wait, I have an idea.” He gave her a confident smile. “When I was over here last week, and I watched you through the window, touching yourself, that was so hot.”

  She gave him a hesitant look. “Yeah…?”

  “Maybe if you do that in front of me, I could, you know, get it up.”

  “Seriously.” She exhaled and just stared at him.

  He nodded. “It’s worth a try, isn’t it?”

  “I don’t think that—”

  “Okay, then.” Brian stood. “How about if I come back tomorrow in the morning? Then we can—”

  “Just sit your ass back down,” Victoria shot back.

  Turing away from her, he covered his mouth to keep from laughing out loud. When he could finally contain himself, he sat down and continued to tug on his unresponsive manhood. Victoria slipped her skirt and panties off as she shook her head in disbelief. She still wore her blouse but was naked from the waist down as she climbed into bed only five feet from his chair. He watched as she pulled the David replica from her nightstand. She took a moment to study it before slipping it in her mouth to moisten it with saliva.

  For a moment, Victoria became fully immersed in giving passionate head to the replica until she spotted Brian’s wide-eyed stare. Then she quickly pulled it from her lips, looked at him as if almost embarrassed, and said, “Sorry.”

  It was just about the sexiest thing Brian had ever seen, and he swore he actually felt his exhausted penis move as he half-heartedly massaged it.

  “Are you ready?”

  “Yeah.”

  She glared at him. “Concentrate, okay?”

  He watched Victoria move the sizeable replica down between her legs with her eyes tightly closed. He mindlessly worked himself as he stared at her, mesmerized. He was married, but he wasn’t dead.

  When he glanced down to find his penis growing, he pulled his hand away from it and attempted to focus on something else. He glanced at the ceiling but quickly returned his eyes to her, finding it incredibly difficult to look away as Victoria went on, blindly engrossed in pleasing herself as if he weren’t even there.

  Slipping the dildo inside her, she held it still a moment while blowing out a long slow breath. When she opened her eyes and found his hand nowhere near his penis, she gave him an angry look. “Hey, Brian, what the fuck are you doing?”

  He grimaced and pretended to work a kink out of his right hand. “Sorry, I uh… my hand was cramping.”

  “You do have two hands.”

  He smiled uncomfortably, began working himself with his left hand, and replied, “I think I’m starting to feel something.”

  Victoria glanced down at his lap and noticed a definite increase in size. She gave him a satisfied smile before closing her eyes and getting back to work. She took a long, deep breath, held it, and when she exhaled, she moaned loudly. She stared at him and said in an almost scary voice, “God, I really miss a real cock… I really miss it.”

  He believed her. He really fucking believed her. His penis twitched excitedly, and his eyes widened as he watched her closely.

  “This is okay, but nothing like the real—” Victoria lost her train of thought as she pushed the dildo as far into her as she could.

  Finding himself totally caught up in her sexy show, Brian stopped moving his hand completely. He stared for another few seconds then shook his head to pull himself back to reality. He shielded his eyes as he repeated the mantra in his head: Stick to the plan, stick to the plan.

  After collecting his thoughts, he took a deep breath and began the final phase of his mission. He began moving his hand over his manhood again, but faster now as he said, “Yeah this is doing it, but could you take off the rest of your clothes? I really think if I saw you completely naked, that would help.”

  Victoria glared at him. “Are you serious?”

  “Yeah.” He painted on an apologetic look.

  Sighing, she dropped the dildo to the bed, quickly unbuttoned her blouse, and removed it, along with her sexy bra. Brian swallowed hard while thinking, I should have gone for that sixth orgasm, after all.

  Victoria went back to work with the dildo and Brian looked down at his erection, which was at half-mast and climbing. She glanced over to him as well, noticed his condition, and smiled. “Good, it’s working.”

  “Would you mind turning around, so I could see your ass?”

  Victoria was so caught up in her activities that she followed his command without giving it a second thought. Turning around, she held the dildo against the mattress as she adjusted her position and gradually slipped on top of it. Slowly she began riding it up and down. He stared at her, getting lost in
the show.

  He whispered, “Holy fuck,” with his eyes locked on the amazing sight and his erection closing in on three quarters full. And while this was an image of Victoria he would never forget, he almost forgot what he was supposed to do next. He watched her bouncing up and down in a trance-like state until Victoria craned her neck toward him and asked breathlessly, “How are you doing?”

  “Uh, okay.”

  Then it hit him. He said, “I, uh, think I need to take the Viagra.”

  “Good,” she moaned. “It’s right over there on the dresser.”

  Brian walked over and grabbed the pill and the bottle of water as Victoria kept going without skipping a beat. Returning to the chair, he slipped the Viagra in his pocket and pulled out the replacement pill. He somehow maintained his composure, even though he found himself unable to look away from Victoria’s spectacular live demonstration.

  He asked, “Could you do one more thing for me?”

  “Uh-huh,” she replied while barely paying attention to him.

  “Would you finger your ass? That would really—”

  “What?” Victoria turned to glance at him.

  “Your ass. Would you finger it a little?”

  She noticed he was fully hard and grinned. She was still caught up in her own fantasy at that moment, turned away from him, and simply replied, “Okay.”

  Brian watched as she bent over further and slipped her other hand behind her back and between her legs. He stared in awe as she ran a finger between her legs with the dildo still in position. Slipping it in, she drenched it with her juice. Victoria moaned loudly, and Brian watched the action closely, suddenly feeling his mouth full of saliva. Like a drooling dog, he ran his tongue around his teeth and then swallowed hard. Brian glanced down at his now-massive erection and then back to her as she slowly moved her finger to her ass.