The lady takes charge

After the door closed behind them leaving Tom and busty redhead alone together, he began to feel a lot of the confidence that had built up coming over here beginning to vanish. The nervousness stayed and for an awkward moment Tom just stood still, scratching the back of his neck and unsure of how to proceed. His nervousness though seemed to make Beth even more turned on as she licked her lips and smiled warmly, "You are sooooo cute, the way you're standing there so horny and tempted but afraid to do anything reminds me of my husband all those years ago." She took a couple steps forward so that her body was pressed right into Tom's, "Do you remember how I helped him out the first time we fucked?"

Gerald blushed as he took a moment to remember the story and then a little longer to verbalize it. "You lied on his dorm bed masturbating. W-when he hesitated too long, you jammed his dick in your mouth?"

Beth leaned in and gave Gerald a quick, soft kiss on the lips. "That is correct. Do you think that might work with you too?" Asking that Beth stepped away slightly from Gerald and with a quick move of her arms and a shimmy of her body, the red dress she had been wearing was now laying in a heap around her feet. Within a matter of seconds her panties lied on top of the dress. Beth took a step around Tom to sit on the bed before sliding her heels off. She moaned as she crawled onto the bed, shaking her plump bottom side-to-side as she did so. She held the pose on all fours trying to entice Gerald who was still fully clothed and kind of stunned by how open and wanton Beth was acting. Even after all the flirting and a couple of stories at the restaurant, he was surprised to see it as she rolled onto her back and begin fingering herself while staring at Gerald. "I don't know if it's the wine or me being horny or what but I swear you've gotten even cuter since we met you. Now stop being such a scaredy-cat and get those clothes off."

He was still nervous about putting his body on display, but he did begin to undress. Shoes. Socks. Shirt. Undershirt. Pants. Then when Gerald had nothing left on but his underwear his self-awareness hit him hard. When he hesitated with that she laughed a little bit and sighed, "just like Frank's first time. You're making me feel like a 20 year old college girl again. But remember we have a time limit so let me help you out." In a moment Beth was sitting up and scooting towards Tom, pulling his boxers down in one swift moment. Tom was already fully erect and Beth knew this was probably the source of his hesitation. So many first timers his age tend to be self-conscious about it. Beth licked her hand to get it wet and reached out to begin slowly stroking it, keeping her eyes staring up at Tom. Suddenly the performance she put on during these hookups, her mask of the horny and flirty tramp fell away though she didn't stop her slow handjob.

Still sitting on the edge of the bed and stroking Tom's dick, looking up at him she actually gave him a serious look. "This isn't my first go-round, and you are nowhere near my first virgin. I get it. You're unsure about your size, worried about shooting your load too soon, you haven't done it before so you don't know what you like, you don't know me so you don't know what to offer to make me satisfied, and even if we figure all that out you aren't sure you can do any of it right. I'm guessing that's a lot of what is going through your mind right now. Am I anywhere near the mark?"

All Tom could do in response is to nod his head and say yes as a distant part of his brain realized how surreal the moment was. Having a woman as gorgeous and intelligent as Beth was, sitting in front of him stroking his dick while suddenly presenting such a serious tone and face to him. It also had an understanding kindness to it that almost seemed motherly were it not for the very unmotherly thing she was doing with her right hand. It was made even crazier by the skilled way her hand moved along his shaft. It wasn't just slow stroking up and down. She would twist her hand around slightly once in a while and let a finger reach out and lightly tickle the side of his testicles occasionally. "So how about this, we both agree not to try anything crazy. We can probably get you off twice before we need to get dressed and meet back up with your sister, so we each pick one little thing to do. I'm sure you have one idea for something you'd like to try. I have a favorite position or two. We each pick one and when necessary and I feel you're doing something wrong, I will tell you so you how to fix it. Does that sound like a plan?"

Tom didn't think long before agreeing at which point the flirty, horny version of Beth returned in full ****. "I would ask you what you want but at this point I don't think I need to ask. While I was getting all serious and asking you questions, your eyes have been firmly planted on these lovely titties that my husband bought for me. I'm pretty sure I know what you want, but I'm going to make you say it. Come on boy, out with it."

"Well, you did that thing in the hallway where you trapped my hand in your dress and your breast was..."

At that point Beth pulled her hand off of Tom's dick and booped him on the nose, "Now, now there's your first mistake. The whole point of tonight is to be fun and dirty. I don't want any biological or medical terms. I don't want to hear the words breast, vagina, or buttocks from you tonight. There are plenty of dirty words for these girls," she slapped one of her boobs as she spoke, "and I want you to use one of those instead."

"Okay, your boobs were so soft and warm. They were so amazing. Since then I can't stop thinking that having them sliding up and down on my pe-, err, my cock would be wonderful." He refrained from using the term penis since she wanted dirtier words apparently and remembering the lesson got a look of approval from Beth who returned to stroking Tom.

Beth leaned forward and kissed the tip of Tom's cock before giving it a quick lick. She didn't look away from it as she spoke to Tom, "So, are you telling me you would like a boob-job?" After confirming it Beth smiled, still not looking away from the dick. "Then I think we need to start by getting this little boy nice and lubed up don't you think?"

Saying that she took her hand and quickly engulfed Tom's entire dick. She didn't pull away though and kept her chin pressed right up against Tom's balls as her tongue began to lightly massage and move around the dick. She remained there surprisingly long and gave Tom the greatest pleasure of his life as he rolled his head back. Before he knew it he felt an orgasm approaching and Beth's hand reach around to grab his ass cheeks while cum began spurting out of the balls, through his cock, and into Beth's mouth. She had grabbed onto him in part so he wouldn't be able to pull away, and in part to help him stay on his feet as his knees began to buckle. The woman continued to keep her her lips firmly pressed around Tom's cock as he came. She didn't pull away until he had completely stopped cumming. At which point she sucked and noisily slid Tom's dick out of her mouth leaving no trace of that orgasm on him. As she opened her mouth to show it was empty, Tom could only assume it was now all in Beth's stomach. "Looks like I got a little carried away there, I think we'll need to get three out of you before going downstairs now. Nice thing about young men your age is the recharge time is virtually nonexistent. In fact you're already getting hard again. Here, you sit down and give your legs a rest while I get to work."

Saying that Beth stood up and moved Tom around to the bed while she kneeled on the floor right in front of him. She pushed his chest to let him know to lie down which he did and quickly his cock was back between her lips. This time she was much slower and more deliberate, also wetter and louder. Moaning more and the sound of the saliva and tongue around was also noisier. The noises alone were enough to get him turned on, add to that the lips and tongue slowly working his shaft and it didn't take long before he was worried that he might actually blow again soon. He was going to say something but right as he began to speak up, Beth pulled her mouth away and placed her tits right above his dick. Tom watched as she use her hands to smash them together, creating an amazingly beautiful and erotic image before she slowly sank down and enveloped his dick within her soft flesh.

As Beth slowly moved them up and down, the fantasies that Tom had before paled into comparison to what it actually felt like. Tom let out several grunts of satisfaction as Beth went to work. Her movements were steady and smooth no matter how fast she moved her tits. A couple of times it felt like he was about to cum but he heard Beth's voice admonish him saying it wasn't time yet before she slowed down. A few times she pulled her boobs away and put it in her mouth again to get it a little more lubed before returning to the titjob that was the best thing that Tom had ever experienced. When she finally decided the time was right, Beth began moving her tits at a speed that astounded Tom and it didn't stop until he felt the eruption start at which point Beth stopped completely and just left the spasming dick firmly pressed between her melons. Once Tom had finally stopped Beth pulled away and crawled so she was lying in bed right beside him. Both were smiling and a little short of breath so she just rested up against her one night stand and had a relatively innocent moment of snuggling.

After a couple of moments she moved up and kissed Tom on the cheek and pressing her cheek against his. "If it means anything, yours isn't anything I'd be too self-conscious about. It isn't the biggest I've ever had but it certainly isn't the smallest. It's probably in the middle if that matters at all." Then in a move that surprised and grossed him out a little bit Beth moved her breasts closer to Tom's face and spread them open a little bit so he could see his own splooge smeared and nestled between her tits. "But this on the other hand is rather impressive especially since you just came not too long before this one. Either you really, really like me or you have some very powerful balls hanging down there."

Tom just smiled and sighed, "How about we say it's a little bit from column A and a little bit from column B. But if you haven't noticed my hand has been laying on your butt for a little while now and with your body laying up against mine, I think I may be able to go soon. Have you figured out what you want to do with your choice?"

"That depends. Do you like the way my ass feels in your hand?"

"I think I like the way everything of yours feels in my hand. But this ass in my hand just might be one of my favorites," saying that he took a moment to be a little bold and gave one of her cheeks a good, firm slap.

Beth made a slight yelp at that but only because it surprised her. After that though she got a very dirty smile on her face and gave Tom a very passionate kiss. "That's my boy, I am so proud of you. Coming out of your shall, slapping your whore on the ass like she needs. But you just keep lying there, if you like my ass so much I think we can do something that will give you an even greater appreciation of it."

Rolling out of bed she stood up , walked over to the foot of the bed where Tom's legs were still hanging off the edge, and positioned herself so that she was facing away. She looked over at Tom with a smile, "I do like being on top sometimes and I do like to have admirers staring at my ass so how about we do both of those things right now." Saying that she reached down and grabbed hold of Tom's cock, slowly lowering herself down until her hot, soaked cunt was right over the tip of Tom's dick. At which point he got worried and started talking about needing condoms.

That got an unironic laugh from Beth who just shook her head in disbelief. "I guess I appreciate you thinking about that but with the lifestyle me and Frank live, do you think there's a chance in Hell that I'm not on the pill?"

Tom just blushed and after thinking about it shook his head and said probably not. With that out of the way Beth slowly lowered her pussy down on Tom's cock and just remained still for a few seconds. "So, do you like my ass when it looks like this?" To emphasize the point she began wiggling it back and forth while Tom's dick remained buried in her. And just like that, the titjob he had received a few minutes ago was now the second-greatest physical sensation he had ever experienced. He moaned out loud which only fueled Beth to do it more. With a smile she looked back at Tom. "Enjoy the view, I'm going to have some fun real quick."

This time Beth didn't tease or play too much. She bounced up and down along Tom's cock while using a finger to add a little extra stimulation and after a while she screamed out loud in orgasm, her convulsing pussy pushing Tom over the edge and causing him to climax as well. After which the two lied down on the bed together for a few while to back in the afterglow. "Well, we have time for a quick shower if we take it together before getting dressed. I definitely need to clean myself up and you're rather sweaty. Care to join me?"

The two showered together, got dressed, and before they went out the door Beth grabbed Tom by the hand and smiled. The flirt-free, serious version of Beth had returned. "I know simple words aren't going to immediately fill you with confidence and all the self-assurance you deserve, but I just wanted to be serious for a moment. Your sister is right. From our short stay together, you do seem like a great guy. You're smart, cute, funny, and you are even a decent fuck. If you're able to work though your shyness and nervousness a little, put yourself out there a little more, I'm sure you'll find yourself a partner one of these days. You are a sweetie and a decent catch. Never forget that." She then leaned in and gave Tom a quick kiss on the lips before turning around, walking out of the room, and heading for the lobby downstairs.