Chapter 07: Sam and George Deeper

Sam and George's Second Date

He said they were going to an upscale seafood restaurant. Sam picked out a dark, knee length skirt and a burgundy silk blouse. She was not going on her first planned date braless. Having their first date with no underwear was odd, but fortunately it worked out well. Even though she and Lisa showed off their tits to the boys, bringing direct attention to them as often as they could, George was a gentleman. Not many boys could avoid making a strong frontal attack. If he found she was not wearing panties it would not have gone well.

The best choice for a bra under this blouse was a dark, very thin one. She really wanted something a bit thicker to hide her pokies, but the wispy one was it. She had matching panties, even though he was not going to see either the bra or panties. She knew what she looked like in them and they made her feel good.

She was checking how the underwear looked in the mirror when her mother knocked. "Come in, mom." Sam said.

Her mom came in and said "If I was wearing that, I would want him removing it from my body by the end of the evening. That is truly sexy."

"I had the same thought, but this is for me. This is our first real date. He is not getting me naked. I might let him feel my boobs. That is, I might want him to squeeze them."

"At least if he does that, it will be nearly the same as being naked. Do you mind if I check?"

"Yes, mom, I do mind, I not want the blouse wrinkled across my tits."

Okay, how about without the blouse?"

"Sure, mom, check me out."

Her mom squeezed her breasts over her bra a couple of times and then just used her fingertips, squeezing her nipples. She said "They pass the thinness test. Now, for a future date, we need to check removability." Her mom reached around and unfastened the bra hooks. Discarding the bra, she sucked one nipple into her mouth, then continued to suck as much of the breast as would fit.

In the meantime, she laid Sam on the bed. Becky's hands pulled off the matching panties and became entirely engaged in rubbing Sam's pussy while sucking on her tits. Sam said "Rub my tits while you suck." Sam replaced her mom's hands with her own on her pussy and rubbed off to a great orgasm.

Sam did not stop rubbing herself and was just able to whisper "Mom, please do yourself." Her mom removed her two garments and worked on herself with urgency to try to catch up to Sam. Sam helped by sucking her mom's nipples. The sucking not only helped her mom catch up, but also propelled her own progress.

Both women had strong orgasms that left them panting. They engaged in a good, long kiss.

"It is decided, I am wearing them. You have calmed my horniness from a forest fire to a long burning flame. He will get a good feel on top of my clothes and I will come home wrinkled and horny. He gets to remove the same underwear on a future date."

"I will get horny just thinking about him feeling you up. We should plan to meet up after."

"Definitely a great idea."

George arrived just in time and was invited in to meet Sam's parents and say "hi" to Jack.

Sam asked "Am I dressed appropriately? I can change."

"You are stunning and appropriate."

They sat across from each other at the restaurant. She noticed him look at her tits once in awhile, but she was used to that with guys. She knew her nipples were poking out just a little bit, but they were not very noticeable to others.

They talked about all the usual first date topics. Sam thought it was a nice, comfortable way to get familiar. She did fumble over the "hobbies" question. Her hobbies of late were showing off, going to nude beaches, and masturbating. She just said "going on nature walks" and that school took up all her time.

They walked around the wharf area. George held her hand, which felt nice. When they reached an area with no people, he kissed her much like the second kiss at the door. She replied in kind. He got more bold and kissed her, even with people around. She liked the jealous stares she got from the other women.

When he took her home, he tried for a little more tongue in the kiss. He was rewarded nicely for his attempt. During the kiss, she pressed her tits into his chest and her hip against his crotch. He had a nice boner going and she did not shy away, rubbing with her hip for a bit. She knew he would have to get off. It was her way to add to her own fantasies.

Unfortunately he was still a bit shy from the 3rd degree from Jack yesterday. Impulsively, Sam took his hand from her shoulder and pressed it against her tit. He let it rest there, so she squeezed his hand. He now squeezed her breast several times and then repeated for the other one. She thought "To me, this feels as good as being naked. I hope he feels the same way." She hugged him again and said "This might be my best second date, ever."

George said "I want to see you again."

"Me, too."

"Is it too forward to see you tomorrow?"

"We have to watch out. This could become a habit, but yes, I would love to see tomorrow."

"How about an afternoon thing?"

"Afternoon, it is. I will call. I can think of far worse habits." She pressed his hand to her tit again and then kissed his fingers. He gave her a nice deep kiss without smothering her.

Sam's parents had already retired, but Jack was up. Her mom must have gotten her fill already from dad. Jack asked "Go well?"

Sam replied "Excellent. He is a great guy. I am not sure why he hangs out with a lowlife like you. We are meeting up tomorrow. See you in the morn, bro."

Sam quickly went into her room and hung her skirt and blouse and peeled off her bra and panties. She laid on her bed and started rubbing her tits. She could still feel his hands on her them. It was almost like she was naked. She was lightly stroking her nipples just the way she imagined George would do it. She needed someone to kiss and suck them. Her own caresses would have to do.

She put both hands on her mound. She let her right middle finger slip into her vagina. She usually just dipped for moisture, but this time she needed penetration. Her whole finger went in. She withdrew it and pushed three in to replace it. She pushed in and out a few times, withdrew them, and used her right forefinger to rub around the inner labia and then around the base of her clit. She then moved the finger to the tip of her clit for three quick flicks. Back to the base to ease the sensitivity. Back and forth twice more and then she started putting her whole finger across her clit and rubbed. Gently at first, but soon fast and hard. Her orgasm started deep in her vagina and spread up into her chest and into her head. Unusual for her, she let out a moderately loud moan with a sharp "Yes!" She wanted Jack to know she got off because of George. She hoped he would have a nice rub.

It was a marvelous orgasm. As she came down from it, she thought "I hope I was not too reserved with George. I think the titty touch and dick press may have shown him I am not too hard to get. I am glad my libido did not take over. He has a nice dick, especially when hard. I really wanted to get down and suck it." And she slept through the night.

George and Sam's Third Date

In the morning she did a long, leisurely rub. What a nice way to start the day. She put on a light nylon robe to join the family.

Her dad and Jack were out, with her mom up.

"Did the underwear work?" Her mom asked.

"The bra was great. He does not know anything about my panty habits, yet."

"Did you get a titty feel?"

"Yes. Not as good as the suck you gave them, but, yes, he felt them both. He is so shy, I had to move his hands to them. The fact that he has not pushed things is so refreshing. That I had to guide his hand to my tit felt good."

"Are you sure he is okay? My only actions with boys' hands was to push them away." She said chuckling.

"Yes, he is fine. His shyness is probably my fault. I asked Lisa to have Jack check him out, so Jack had a talk with him and probably told him to keep his hands off! If he is shy because of what Jack said, I am fine. I do not mind pushing him to be more sexual. I think he likes me pushing him along."

"Maybe you should have had him suck them."

"I'm not waiting any longer for that, maybe today."

"Again? Three days in a row?"

"Yes. I really like him and he seems to like me."

"Well, if you are going to do it today, you do not need me."

"Need you for what?"

"A post-date titty suck."

"Mom, I can always use one of those from you, even if someone else has done it." Sam opened the robe and said "Please?"

Her mom took off her shirt and said "Only if you do me, too. I did not get a suck yesterday."

"Not from daddy?"

"Yes, he did a good job on them. I need a post-coitus suck."

"Can we sit on the sofa?"

They went to the sofa and kissed with familiarity and lust, starting soft and moving to deep, open-mouth kisses. Sam fondled her mother's breasts. She noticed her mom had not touched her, yet. She took one of her mother's hands and placed it on a breast and then, like with George, squeezed her hand so her mother would fondle them. Sam repeated the process with the other hand so that her mother was fondling her daughter's breasts with both hands.

Sam lifted one of her mother's breasts into her mouth and pulled the nipple in enough to rub her tongue over the aureola and flip her tongue over the nipple. Her mom kept massaging Sam's breasts. She was focused on the nipples. Her mom raised her mouth back up for another solid kiss. Sam coaxed her mom onto her back and positioned herself so they could both fondle each other's tits and kiss them at the same time.

Sam was kissing one nipple and reached to her mother's pudenda. Sam was acutely aware that it was not far from her mother's nipples to her pudenda. It is not the first time she has been tempted to go down on her mother. She thinks her mom has grappled with the same thing.

Sam kept up tonguing and sucking her mom's nipples while she began her usual stimulation of her mother's genitals. A little dip in the vagina for moisture, but she thought her mom might want more. Her kisses and tit play was more intense this morning. Sam did what she did to herself last night. One finger deep and then three. She curled the fingers up and was rewarded with her mom's intense hug, pulling Sam's tit onto her mother's mouth much tighter. Sam started to rub her mom's clit, but did not get far before her mom's climax took over.

They hugged a little tighter than usual for a post-orgasm hug. It felt very comforting to Sam. Her mom kissed Sam in a little daughterly fashion. BSam said "That was great. Thanks for the post-date titty suck."

"And you, too for the post-coitus suck and orgasm. I really needed both. You are right, it is sexy having you guide my exploration of your body."

"I hate to ask, but are you getting what you need from daddy?"

"Absolutely, no complaints. I have found that I am needing more sex lately. With everyone being naked so often, it seems both of us have a higher libido. Mine seems to have doubled by needing it from him and from the women. It might even have tripled to be him, you, and other women. Your father has stepped up his game."

Her mom said "I want to do you, now." Her mom looked down at Sam's pussy as usual, but there seemed to be more this time. Sam thought "We need to address cunnilingus soon, but not today."

"I would like you to do me. Would you mind if I helped?"

"Am I not doing it right?"

"Oh, nothing like that. You seem to understand me better than I do myself. I just want to experience it both ways. You start."

Her mom laid Sam on the sofa this time and took Sam's starting approach of one finger, then three, and started teasing all of the surfaces. She did this while kissing Sam's tits.

Sam squeezed her own nipples and her mom stopped. "Mom, don't stop," Sam squeaked. Sam would squeeze a tit while her mother tongued the nipple and then her mom's tongue would compete with Sam's fingers as Sam did her own nipple. Sam dropped both hands to her pussy where three sets of fingers danced around. Sam came in a very satisfying climax.

"Thanks mom," Sam said in relief. "I may try to get an orgasm from George today. Is that wise? Are you okay with it?"

"Yes, honey, I am okay with it. Maybe it calls for one more date, but it sounds as if postponing it might just be posturing. You really like him?"

"Yes, mom. He is the best boy I have ever met."

"I am glad to hear it. Let me know what happens, okay? I love you, Sam."

"Love you too, mom. That was a great orgasm, by the way. You do know me quite well. We need to try the me-and-you method on you, mom. Maybe with one of your girlfriends. It was great."

Sam called Lisa to bring her up to date on George. The first kiss, first real date, first booby touch, first deep kiss. A third date with no plan except possibly an orgasm.

Lisa said "You are moving fast girlfriend. Jack did boobs on the second date, but maybe five dates until we both came."

Sam admitted "Yes, I am, but it just feels like time to do it. It isn't like I am going to fuck him. Probably just masturbation with each of us doing ourselves. I do want him to feel me up, though. I need fingers on my pussy."

"Give me five, I will be right there." And before Sam could object, Lisa hung up.

"Mom," Sam announced, "Lisa is coming over to finger me."

Her mom answered "That's nice dear, can you do it again so soon?"

"I think so, but if not, I will tell her I just jilled off and need a few minutes. I am not going to mention you."

"Maybe for the best. I guess I will leave you two to go at it."

"No need to leave. You have been with us before and you like doing Lisa. It is a game three can play."

"How about I call Sally. You and Lisa can go to your room until Sally gets here and you want to join us."

"I have to leave in two hours."

"No problem. You ladies can leave and Sally and I can keep playing. Or you can leave and the three of us can play."

Lisa came in braless in a skirt. Sam lifted the skirt to verify that there were no panties. Sam's mom said "Cute outfit, Lisa."

Lisa said "Thanks, it is just an old thing."

"Not referring to the skirt and shirt. The rest is quite young and very cute."

Sam interjected "Mom, are you trying to make time with my lover?"

"Maybe."

"Fine, I'll leave it up to her."

Lisa went over to Sam and said, "Even if we have flings with the other's mom, you are still my main side dish, lover."

The two girls kissed deeply.

Sam's mother said "Maybe you should take this behind closed doors."

Sam replied "We will go into my room, but the door is never closed to you."

"What if George is in there?"

"Then we will renegotiate. He might be into threesomes with older women."

"Your father is not going for that."

"Maybe foursomes with older couples."

A few eyes lit up when her mom just said "hmmm." Sam and Lisa went to Sam's room.

Sam said "We only have a couple of hours before George comes."

"If you have him coming that soon, you are going to throw your mom for a loop."

"Dirty mind. 'Arrive', if that suits you better."

"Sure, but if you want to come, we should start."

"It might be good to not be so anxious. I jilled just before I called you."

"You want to make out? I love that."

Sam grabbed Lisa and started back into the kiss. BThey laid down on the bed for more comfort. Just then they heard "You are right, they are involved." It was Lisa's mom. She continued to them, "Sorry to interrupt. I will leave you to it."

The girls got up and went to the family room to see their moms making out on the sofa. The girls went to the loveseat and continued their kiss. Lisa put her hand under Sam's shirt to play with her tits. Sam did the same with Lisa. Their moms mimicked the maneuver.

Lisa's mom started panting and pushed Becky's mouth down to her tits and lifted her shirt. Sam's mom started mouthing Sally's tits. Sam copied the move on Lisa. Lisa whispered "I need to come. I need to do it." Lisa put her hands under her skirt, rubbed a couple of minutes and came. Sally came shortly after.

They all took a break from the make out session.

Sam started with "I need a plan for today. Sally, I think I want to have an orgasm with George today. I will play it by ear on that. My first order of business is an old fashioned make out session. Much like what we just did. Breast rubbing. Maybe a pussy feel. I might touch his dick through his pants, but I already did a hip rub. He definitely noticed.

Sally asked "Big dick?"

Lisa groaned "Mom!"

Sam ignored Lisa's protests and answered "Sort of average size. Felt nice on my leg. I wanted to suck it last night."

Sam's mom groaned "Graphic."

"You want PC or the truth?"

"Maybe those are not the only choices."

Sally asked "What kind of orgasm? Self-induced, hand job, fuck?"

"No fucking. I am thinking get him turned on with dick, boob, and cunt feels and finish with straight masturbation. I will probably try to give him a hand job. I am looking forward to blowing him."

Lisa said "I like that."

"I know you do, lover."

Lisa's mom beamed at the girls' familiarity.

Sam's mom, "Graphic."

"But necessary. No plan means bad feelings. We have to manage mens' egos. So, first make out. Take a break for dinner, then if it is still okay, the big 'O.' But, where to make out? I thought of here, the pond, the make out place, or a matinee."

Becky said "Here is good. I can leave, or pretend to leave and peek."

"No peeking." Which left her mom with a frown. "Yet." Her mom's eyes lit up.

Sam continued "Too many beds, a flat sofa. I want to make out sitting up. Even with all the negatives, 'here' is still in the running.

"Too much risk at the pond. Needs to be relaxed, romantic. Same issues at the make out place in broad daylight. So, the lead right now is a movie matinee. Most likely the nosebleeds will be vacant. Critiques?"

Sam's mom said "Do it here. You can keep him upright or you show him the door. I will peek to make sure he behaves."

"No peeking!"

Sally said "Make out here. I will peek with your mom." Sam gives a big sigh.

Lisa said "I vote for here. I prefer to peek, but I will get your brother off, oops, I meant out. We will come back at a good time, go to dinner, and then maybe a movie, or the pond, or both. Can we get your dad off?"

Sam's mom said "It will prevent me from peeking, but I will offer your dad a blowjob in a public place. He really wants to do that."

Sally asked "Oh, I think Bob would like that too." Can we double date?"

"Oh, that would be great. We just need to figure out where to go. We can do the pond and clear out before the kids come, I mean arrive. We need to work the script. Sam has me scheming now."

Sam said, "Good. Invite him in for snacks. Serve at the sofa, mom takes her leave, and then make sure we start off with some snogging. After one and a half or two hours, we go to dinner and then either theatre and then pond, or just pond.

Sam's mom said, "Darn, no peeking. I will rendezvous with your dad. We will pick up Sally and Bob for an early dinner. Go to the parking lot for a public blowjob. Go home and come again."

Sam said "I never got my orgasm, sweetheart."

Lisa dove in with deep kisses on Sam. Her mom did the same to Becky. Both dispensed with preliminaries and went straight to clit massage. Both women came quickly.

Lisa and her mom went home to dress in a way to encourage romantic make out. Sam chose an above the knee, loose skirt, a button down shirt, a thin cotton bra and matching panties. She liked the sensuous feel of the thin cotton and the panties formed a nice cameltoe and the bra emphasized her pokies. The shirt let the pokies show. It also let her boobs sway and bounce. Her mom liked the choices and chose similar fashion.