The following days continued to move along for the three of them with the typical stuff. They were filled with work, meetings, lunch dates, shopping, running errands, etc. The weather forecast for Saturday was calling for rain; so since Randy wouldn't be golfing, the girls decided Friday would be the next 'therapy session' for Jo and Randy.
Sarah decided it might help Jo a little more if they set it up like an actual date. She planned the whole thing. She made reservations for a nice restaurant, picked out Randy's clothes, and told him to pick Jo up at 6:30 with flowers in his hand. There would be some dancing at a club after, and then back to Jo's condo.
Jo enjoyed it immensely. There was no uncomfortable getting to know you conversations that normally happen with new dates. There was already a guarantee about physical contact of some sexual sort after the date so that eliminated even more nervousness. Even though she knew it was a setup and why it was all happening, it was the best date she'd been on in probably 5 years.
They were sitting on her couch making out again when Jo reached down and began rubbing Randy's crotch. His cock strained against the fabric and felt just as hard under her hand as it did pressed against her stomach when they were dancing earlier.
She slipped off the couch and moved between his legs on her knees. She took off his shoes and socks and began to undo his belt when his hands grabbed hers. "Are you sure this is want you want to do?"
She nodded as she shook away his hands and continued to try and extricate him from his pants. "Honestly, I've been thinking about it since last week. You felt so good in my hand. I promise that I'm not going to stop this time though."
He lifted his hips up and helped her ease his underwear down, exposing his hardness to her. After getting his pants and underwear completely off and throwing them on the other side of the coffee table, Jo looked at her prize and licked her lips. Her fingers gently traveled along his length a few times before she wrapped her hand around him. Up and down she moved her hand, slowly at first, until a few drops of pre-cum began to form at the tip.
Her hand moved over the head, smearing Randy's pre-cum around, making it easier to stroke him. She continued to use steady long strokes on him. Anytime a new drop of pre-cum appeared, her stroke would go all the way up over the head, collecting it, and coating it all over him with the finish of each stroke.
Randy had been moaning softly since she had first touched him, but was now quite vocal in his praise and adoration of the things Jo Ann was doing. Her pace began to quicken but then she suddenly stopped, holding Randy's cock by the base. She leaned forward, closed her eyes, and licked him once. Her tongue traveled from just above her hand, all the way up the underside of the shaft to his crown. He shuddered at the feeling that came over him and told her so. "Oh shit, Jo. That was awesome. I'm not going to be able to last much longer, baby."
She resumed stroking him, quickening her pace. She added a twist of her wrist near the top of her stroke. That twist combined with an unexpected open mouthed kiss that she planted over the head of his cock, pushed Randy past the edge. "Oh, fuck; I'm gonna cum, Jo!"
Jo managed to pull her head away just in time; she didn't think she wasn't ready to have someone cum in her mouth yet. The first big blast shot out and landed halfway up Randy's chest onto his shirt and tie. As Jo continued to stroke him, the second blast managed some airtime before landing well above his trimmed patch of pubic hair. The third found air as well; this one splashing down on his pubes. The next three spurts were weaker, but still flowed generously out of the tip to fall down over Jo's knuckles. There was quite a lot of it, too.
Jo Ann was proud of what she'd done. She even surprised herself more when she licked a little of Randy's cum off of her hand before pulling him up and taking him the bathroom to help get him cleaned up. She removed his shirt and tie, promising she would have the tie dry cleaned, before taking a warm wash cloth to him. Once clean, she leaned up to kiss him. She felt his cock already starting to stir in her hand as their tongues danced in each other's mouths.
She broke the kiss and looked at him. "Randy, will you take me to bed and undress me?"
"It would be my pleasure." he told her. He took her hand and led her back to the bedroom and stepped behind her.
"Randy, hang on a second." she said as he kissed her neck gently and his hand touched the zipper on the back of her dress. She looked back at him and he could see the nervousness on her face. "No man has seen me naked or touched any part of my body since I was raped. Except for the kissing and making you grab my ass last week, there has been nothing but my own fingers making me feel good. Until now, I've been in control of everything. Giving that up may be hard for me, I don't know, so please promise that you'll be extra gentle. I might not make it through it this first time. I want you to understand that if I do end up stopping you, it wasn't because of anything you did. I wouldn't even be this far along if it wasn't for you. I love you, Randy."
He moved back around her and hugged her. He grabbed her face with both hands, gently lifting her face to his, and kissed her. "I've got you, Jo. Nothing bad is going to happen to you as long as I'm here."
Randy moved back behind her and placed a couple of gentle kisses on the left side of her neck, trailing his tongue up until he was able to gently bite and tug on her earlobe. His hand grasped her zipper and began moving it downward slowly as he whispered in her ear. "I love you too, you know. You're safe with me. I'm going to take care of you."
With the zipper finally at the bottom, Randy moved around in front of her and kissed her firmly on her lips. His tongue found hers, distracting her, as his hands reached back to spread the back of the dress open and pull it forward past her shoulders. It started to fall to the floor but was held up where her breasts were mashed against his chest. Randy kept his eyes closed and stepped back to let the garment fall to the floor.
"You doing okay, Jo?" He could hear her hesitation so he sought to calm her. "Remember what you told me last week? How you had seen me in a swimsuit hundreds of times? Well, I'm imagining what you have on right now and I'm guessing that I've probably seen you in bikinis that reveal more. You know I'm right so I'm going to open my eyes now, Jo."
Randy opened his eyes. She was beautiful as she stood before him; totally different than his wife but beautiful just the same. Jo was just 5'3" to Sarah's 5'8". Both probably weighed about the same but carried it differently. Sarah was tomboyish yet still very feminine with firm, small to medium sized breasts, very slim hips flanking a tight tiny ass, and dark wavy hair just barely reaching past the tops of her shoulders. Jo Ann was more on the voluptuous side; very full large breasts, wider hips, and blonde hair almost down to her waist.
She smiled back at him for a moment but then frowned when she heard him go "Hmmm" and chuckle just a little. "What the fuck was that for?" she asked him.
"Oh, nothing; you're totally beautiful. I just figured you for a frilly, lacy underwear kind of girl. I wasn't expecting the lumberjack flannel." He continued to smile and stare at the bikini briefs and front clasping bra both made out of green and black buffalo plaid flannel.
"They match and they're comfortable as hell, you asshole." she shot back at him with a grin.
"And you look great in them, honestly. But it doesn't matter, because I'm going to have you out of them before long." Randy got a small squeal out of her and her eyes went wide as he scooped her up and laid her on the bed behind them.
He climbed up next to her and kissed her again. She could feel his hardness lightly brushing up against her hip. She wrapped her arms around his neck and kissed him back. As they continued to kiss, his hand trailed down her neck to her chest and stopped at the top swell of her breast. Randy felt her tense a little so he moved his hand across her body and continued his downward path along the side of her torso, avoiding her large breast altogether despite how badly he wanted to touch it.
Stopping at her waist, he let his fingers dance over, lightly tickling and tracing circles around her belly button before moving back to the side and continuing on down past her hip with just a small teasing tug at her waistband. He reached as far south down her leg as he could go, grabbing her behind the knee and pulling it up towards them; locking his elbow underneath it as he intensified the assault on her tongue.
He leaned farther toward her and moved his knee between her legs, grinding his bare hard cock against her hip. His hand moved to the now raised backside of her leg when his elbow released its hold and began its slow teasing journey back north.
Randy paused when he reached the spot where her underwear stopped at the bottom of her ass cheek. He moved up and cupped as much of her ass as he could in one hand and squeezed. She moaned into his mouth as he did it. He slipped one finger under the elastic and ran it along her ass and up to her hip. A firm push against her hip towards the mattress turned her slightly away from him for just a moment, grinding her other hip even harder against his cock.
He trailed back over to her belly button, but instead of moving back to the side, his hand travelled due north, stopping when his hand brushed the underside of her tits. Randy gave her a quick whisper in her ear before proceeding. "I'm going to touch them now, Jo. Fuck, you feel good."
Partially nervous but mostly excited, Jo was panting heavily when he began lightly following the curve of her breast and up along the side, dragging the backs of his fingers along the outside of her bra. Once he had made the complete trip around, his hand flipped over and he palmed her large breast. A light squeeze from him was met with a loud groan and both of her hands pulling his head down roughly to meet her in a tongue filled kiss.
"Are you ready?" he whispered to her. He didn't really wait for answer as he moved his kisses down her neck to the tops of her breasts.
She didn't even realize he had opened the clasp of her bra until she felt the weight of each of her boobs shift towards the sides of her body, causing her to gasp. They were still contained within the material of her bra but she had a feeling they wouldn't stay that way for long.
Randy continued kissing and licking all across her chest, neck, and lips. He continued to squeeze her breast gently, alternately running the back of his fingers along the underside of her breast, across her stomach, and down her hip.
With his hand's next trip back up her breast, Randy pushed one cup of her bra, and then the other, to the side; exposing all of her naked chest to him. Her breasts stood proud. For a naturally large breasted woman in her early 30's, there was surprisingly little side sag to them. Her areolae were smaller than he had imagined, probably no bigger across than a quarter; dark brown with a proportionate sized nipples that appeared to be just as hard as his cock was currently.
