When Madeline agreed to go on a road trip to help Sam and Michael with a mission, she hadn't anticipated sleeping in a hotel with only one queen sized bed. She was thinking they would have a room with two beds, but she was proven very wrong. Sam had offered to sleep on the ground, but she knew his back wasn't what it had been, so she said as long as they both stayed on their side, he could sleep in the bed with her. Besides, she had shared a bed with worse company then Sam when she was married to Frank all those years. Both of them stayed true to staying on their sides for most of the night until Madeline woke up at four in the morning to a warm arm wrapped around her waist. She felt Sam's strong chest against her back. As she stretched her back into his body, she felt Sam's hard cock against her lower back. She was a little surprised, but it wasn't unusual. She was used to feeling that against her lower back form when she slept with her husband. The difference between Sam and Frank, however, was that in his drunken sleep, Frank would try to take advantage of her. Madeline laughed and tried to move out of the warm embrace Sam had her in. But her movement woke him up. He softly groaned at the sudden disappearance of heat that radiated from the older woman.
"Sorry, baby," she said. In that instance, she decided not to bring up that his hard cock was felt against her back. "I need to go to the bathroom," she said softly as she made her way to the bathroom. She figured he already knew why she had moved, so she made her way to the bathroom and closed the door behind her. She waited a few minutes before making her way back to the bedroom, where Sam was sitting against the headboard with the sheets covering his body. He was a little embarrassed at the whole situation as Madeline made her way to her side of the bed and climbed in. When she was settled into the sheets, also leaning up against the headboard, Sam looked over at her.
"Sorry," he said softly. He didn't want it to be awkward between the two of them. It was already awkward enough that he was cuddled up against her with a hard on pushed into her back. Madeline's head immediately turned so she was looking at Sam, a little surprised at the apology. She wasn't expecting an apology.
"It's fine," Madeline said. She knew it wasn't voluntary, but she was still a little flattered. "I've had worse happen," she added. Sam looked at her curiously. She trusted Sam. She also seemed to spill her guts to people she trusted when it was four in the morning and the lights were off. It was like there was a safety net and she didn't have to worry about anyone telling her secrets. "Whenever Frank would pass out from the alcohol, he would grope me," she said, quieter then before.
"I'm sorry," Sam said again, this time for what she had to go through. "You don't deserve an asshole like that," he said. He had heard stories about the late Frank Westen from both Madeline and Michael, so he genuinely thought she deserved better. Madeline smiled as she moved Sam's arm that was closest to her and wrapped it around her shoulders so she could move closer to him. She rested her head against his chest and they stayed there for a few minutes, sitting in silence.
"Can I tell you something?" Madeline asked. She wasn't quite sure why she was about to tell Sam what she was about to tell him, but again, she knew she could trust him and if she wanted anyone to know, it was Sam.
"Of course," Sam said as he planted a soft kiss on Madeline's head.
"I've never had an orgasm from another man," she said. She had given herself plenty of orgasms over the years, but never had she been to bed with someone and been given an orgasm. Sam turned his head and looked at Madeline with surprise.
"Never?" he asked, the surprise evident in his voice. "Even Virgil?" he asked. Madeline softly laughed at his surprise.
"Even Virgil," she confirmed. Madeline was a beautiful women. It was shocking that a man didn't take the time to give her what a woman deserves. He had never thought of her like that, but he now had a mission to change that.
"Would it be okay with you if I changed that?" he blurted out. He wasn't expecting that from his mouth, but Madeline Westen deserved more than that.
"What?" Madeline asked, surprise written on her face. It was now her turn to be surprised. Sam decided to just go with it.
"Yeah," he said. "I can't let you live your life without someone ever giving you an orgasm," he added. "And it'd only be between the two of us. No one has to know." Madeline became eerily quiet at the proposition. The eery part was that she was actually contemplating it. She figured if it was going to be anyone, it might as well be Sam. She trusted him more then anyone, despite the fact that he was Michael's best friend.
"I don't know, Sam," she said. She was still on the fence about it, but when Sam leaned over to place a soft kiss on her lips, she didn't protest. He let her deepen the kiss before letting his hands wonder to the button up plaid shirt she was wearing that was once Frank's. He started unbuttoning the shirt, freeing her breasts more and more with each unbuttoning. She had taken her bra off before going to bed, so he didn't have to worry about trying to take her bra off. When all the buttons were unbuttoned, Sam moved the shirt down her arms until it was completely off.
"I don't know about this, Sam," Madeline said as she pulled away from the kiss that was starting to heat up. She pulled the sheet up so it was folded against her breasts. "Are you serious about giving me a…" She looked up at Sam, a look of embarrassment written over her face.
"An orgasm?" Sam asked. He couldn't help but to smile at the sudden embarrassment that washed over Madeline. "Of course," he said. "You're a beautiful woman. You don't deserve to live your entire life without experiencing an orgasm from the hands of another man," he said. "Especially when it's from someone who cares as much about you as I do," he added. Madeline couldn't help but to smile at what Sam said, so when he leaned in for another kiss, she softly reciprocated the kiss. When they broke their kiss, Sam continued planting soft kisses along her jaw line and then slowly down her neck. When he got to her collarbone, he slowly moved the sheet away from her breasts while he continued kissing her soft, feminine skin. When Madeline let him move the sheet away from her breasts, he continued trailing kissing down her right breast until he met her nipple that was softened from breastfeeding and age. His tongue then flicked out so he could taste the tip. He could feel Madeline's breath hitch from the teasing of her breast. A smile formed around her nipple and he softly laughed, which vibrated against Madeline's breast. She groaned his name out as he switched to the other breast, giving the same amount of attention as he did the other one. He could feel her hips rock against the air as he continued trailing his kisses down her body, over her soft stomach and then to the soft, grey triangle of hair between her legs. He was surprised at how wet she was, but she wasn't quite ready for him to touch her yet, so he let his hands wonder back to her breasts and softly cupped them as he trailed kisses back up her stomach. As he made his way to her breasts, he looked up at her only to see her head tossed back on the pillow. She had never felt anything quite like she did at that moment, which was evident to Sam. How could anyone not let this woman feel what she was feeling at that moment? He was now finally starting to understand how much of an asshole Frank Westen was. What was most surprising to him was that not even Virgil had paid her this much attention. After a few moments of cupping her breasts and softly fondling them, he let a hand wonder back to her womanhood and that's when he noticed she was finally wet enough for him to do his thing, so he trailed his kisses slowly back down her body, kissing each breast as he passed over them until he made his way to her sex. Madeline's breath, again, hitched in her throat, which then turned into soft panting.
"Awe, yeah, Sam," she groaned as he nuzzled her opening, letting his tongue flick over her sex. Madeline's entire body started to quiver, her thighs parting wider as his tongue teased her inner, pink lips. His hand reached up and cupped her breast, his calloused thumb rubbing against her nipple, which hardened again. Madeline's hips rocked more and more as Sam let his tongue wonder inside her lips. It dipped in and out as Madeline's thighs opened as wide as they could. Her hips continued to rock at the sensation. The soft moans and the sensation that was evidently building up in Madeline soon became part of Sam's pleasure, so he became hard himself. But this one wasn't about him - he wanted Madeline to enjoy this. That's when he let the hand that wasn't cupping Madeline's breast wonder to her sex, which soon replaced his tongue. He then pursued her clit, which he found within a few seconds. When his thumb also entered her sex, Madeline gasped with pleasure. He soon softly took her clit between her thumb and pointer finger so he could softly rub it, which brought Madeline even closer to her orgasm. Feeling her thighs spasm, her hips arch up from the bed, and her clit pumping against his fingers, he substituted his fingers for his tongue and then softy sucked once before Madeline's body succumbed to the orgasm, her breath leaving her body momentarily. She then let out a sigh of relief at the sensation of finally having an orgasm.
"Holy hell," she muttered under her breath. She relaxed into the bed before he started teasing her clit again. "Sam…" she warned. She knew that if he were to start up again, it wouldn't take much to push her over the edge again. He lowered his head again, but before anything could happen, she grabbed his hair and pulled him up. "Fuck me," she said as she quaked in his embrace. "Now," she said, cutting him off before he could say anything. He wasn't expecting what she said, but he immediately obliged and freed his still hard cock from his boxers and centered himself in between her still wide-open legs. His cock quivered at the touch of her wet womanhood against the tip of his cock as she reaches down and guides him to her and positions him. Feeling the tip of his cock teasing her womanhood, she wrapped her legs around his hips and pulled him closer to her body. He then thrusted himself inside of the woman he had just given an orgasm to and slowly started a rhythm of thrusting as he dragged his cock against her inner walls. "Hard," she said. He then slowly started to pick up the pace as he felt himself come closer to climax. He kept the rhythm steady for a while until he couldn't stop himself from reaching his climax. As much as he tried, he started to speed up his rhythm. She felt him pound into her, his rhythm getting faster and faster as she moaned his name.
"I'm about to come," Sam said in between moans. He never expected to get fucked quite like he did with Madeline Westen, nor did he expect his climax to reach so soon. But whatever Frank Westen and Virgil had done, they missed out considerably.
"Stop talking," is all Madeline could get out.
"Maddie," Sam said. "I'm going to come," he said in between each moan. Madeline just buries her head in Sam's neck as she comes, her inner walls clinching Sam's cock. Within seconds, Sam comes and he collapses on top of Madeline. Madeline holds him against her breast while he recovers. Despite the fact that Madeline had never had an orgasm, she really knew how treat a man when it came to sex. He then rolled over next to Madeline. The older woman immediately cuddled close to the sweaty body next to her, burying her face into his shoulder. He moved his arm so it was wrapped around Madeline's body. She cuddled as close to him as possible, tucking her head into the space between the mattress and Sam's neck. Two orgasms in one night was more than she had anticipated and her eyes dropped because of it.
"Go to sleep, Mads," is all Sam said. Madeline immediately obliged as she closed her eyes, her breathing also slowing down. He smiled and kissed the side of his head, also falling asleep. The rest of the morning was spent sleeping next to each other, embraced in each other's arms.