Neighborhood Moms and Daughters

Samantha first shot back with: "Mom, how do you know size matters?"

Teena said that she had to think quick and said that it was from experience before she had met Rick. She added that she had also looked for additional stimulation which resulted in the toy box. Teena added: "That didn't end the conversation though"

Samantha had added in a sympathetic tone: "Mom, are you and dad having issues? I know he is off on another boy's week."

Teena said: "I had to be honest with her and told her that we were not doing well. I was frustrated with his singular interest in sports, him getting fat, and not paying enough attention to me. I told her that I literally took things into my own hands." Samantha laughed at that comment which helped further diffuse the tension."

Teena said that Samantha then said: "Well mom, you certainly got your hands busy by what I have seen in that box. I mean, you could keep a small army satisfied with those toys. Since we are being open, I did have some questions about the different toys. I noticed various plugs for your ass. Is that something you are into?"

Teena said: "I had started the conversation to get more insight into my daughter but now the conversation turned back on me. I had to talk about my anal fixation which she was curious about. I expect some of my plugs may go missing in the coming days. She then went on to ask the hardest question which was about the strap on. She asked if dad was into some kinky stuff, or did I have a friend to help relieve my frustration. I stumbled on this and claimed that it came as a package with others. I don't think she believed this story though. This morning she came down for breakfast looking all perky. I bet she gave Mr. Red a workout last night. She then started asking for more sex advice."

Teena said that she had given Samantha few pointers on oral sex about what to do and what to ask for. Teena was glad that Samantha had opened up to her, but she was worried that she would find out about what she had been doing with Denise and me.

I said: "Wow, that was an intense discussion. I am not sure how I would proceed with her. I wouldn't want to shut it down with lies or deception though as you could damage your relationship with her."

Teena said: "I thought it through after breakfast and came to the same conclusion. I care more about Samantha than I do about Rick. I just have to figure out how to broach it. She went out to her dance practice this afternoon and I came straight here to talk to you."

I reached over and gave her comforting touch and added: "Teena, you are a great mom and an incredible lover. Any advice you give Samantha will go a long way. Don't lose the opportunity to connect with her. You want her on your side when your relationship deteriorates with Rick. You have the perfect week to figure it out."

Teena thanked me for being a patient listener and the solid advice. She said she had to get back home in twenty minutes when she expected Samantha back. As she said this, she reached out and started stroking my thigh that held my member. She said: "Ray, I should go soon, but I don't want to leave you ignored." She got off her chair and came kneeled on the bottom of my lounge. She reached up and grabbed the waist of swimsuit and peeled it down. She quickly started blowing me by stroking me in time with her sucking. Her position on the lounge didn't let her deep throat me much, but her technique was flawless. I only lasted about five minutes and blew my load in her mouth. She didn't miss a drop and looked at me in the eyes as she swallowed it.

She then got up and said she should get back to her home.

I stood and said that by her own estimate she had fifteen minutes left. I guided her lay back on her lounge chair. I followed her move of reaching up and pulling down her panties while leaving her dress on. I then pushed her legs up and open and took a long lick from her anus to her clit. She was already moist, and I knew I would need to work quickly. I kept my tongue on her button and inserted two fingers in her hot, wet cunt. I then pulled then out and put one finger in her pussy and one finger in her anus. This got her moaning. I moved my fingers in and out and kept licking her pussy from my finger to her clit. She came for me in less than five minutes. I looked up at her with a smile and asked: "How would you coach me to be better?"

Teena said: "That was wonderful."

I added that while I appreciated the compliment, she should get her daughter to be more specific in the giving and receiving of feedback to get better satisfaction. It is all about communication which is both verbal and non-verbal.

Teena said: "You are so right. I will talk to her about it"

Teena then got up to go. I threw her underwear at her and said that she might want those. She just threw them back at me and said that I should sniff them tonight.

The next morning, I got a call from Teena asking if she could come over to discuss more. After I agreed, she said she would be over in ten minutes. I was doing a workout in my new gym clothes and was just grabbing water while toweling off my sweaty head when the doorbell rang.

I went to the front door to greet Teena but then quickly realized that there were two people there. I opened the door to find Teena and Samantha. I greeted them both as friends and gave Teena a questioning glance. Teena took it all in stride, like she did any situation, and announced that they had come to get advice from the source.

"The source of what?" I said.

Teena said: "The source of information on the male psyche and male preferences. We have been talking about men and boys this morning and I tried to represent their views but realized that I am not the best expert we had available."

We moved to the living room with Teena and Samantha taking easy chairs and me on a couch facing them. After we all got comfortable, I said: "I hardly qualify as an expert but ask away."

Samantha was looking very sheepish about this conversation, but Teena was steamrolling ahead with it. She said: "Ray, we have been talking about boys and men and what they like and how they act. Rick is out for week on his fishing trip. You are a close friend and third party who will be less biased about these questions as Samantha isn't your daughter. The questions are about relationships, but also around sexual preferences. We need real, candid answers as Samantha is dating and having some challenges with boys.

I promised to try my best to give honest and insightful answers.

Teena started on boyfriend/girlfriend relationships. She asked what expectations I had as boy when I was first dating. I talked about the initial physical attraction that was important for many men.

I talked about going after girls that I thought were beautiful. I added that if the beauty isn't backed up by a personality that stimulates me, the interest dies quickly. My advice when dating boys was to dress classy and don't every be afraid of displaying your intelligence. Guys that intimidated by smart women are guys that you don't want to date. Samantha was quite tall as well (almost six feet) and I knew many guys would find this intimidating as well. I suggest that she walk tall and be proud of this as well, and that guys who couldn't handle tall girls were good to get weeded out early.

Teena asked when was the right time to become intimate?

I said: "There are a lot of factors. Are you ready? Is he ready?" I laughed at this question and added that boys were almost always ready, so you need to manage yourself more than him. That got a little giggle out of Samantha which helped break the tension. I went on: "In my opinion, make sure he knows you and that you like him. Don't be too quick but that is easier said than done." I went on about a getting a private location and during the evening, not to go too quickly. Again, easier said than done.

Teena then moved on to what I knew about guys views on sex.

I said that she was going to have to be specific.

Teena said, "Give me your view on blow jobs."

I stalled for a second and sip of water. I said: "The easy answer is that all men love blow jobs. The longer answer is that there is good oral and less good oral."

Samantha spoke for the first time and asked: "What makes for a good blow job?"

I said: "That is complicated, but I will try. Good oral sex starts before the act by creating anticipation and displaying confidence by the giver. Give them indications that you want to do it and find it exciting. The biggest turn off is if he thinks that you think that this is a chore or something you find offensive. Communicate your desire with words and nonverbal cues. Next in your understanding is technique. Some simple rules here: no teeth, spit is good, and don't just use your mouth. No teeth is obvious. Spit adds lubrication and looks very sexy around a woman's mouth and in strings of it coming from the mouth. Using your hands is almost always the right call. You should stroke him up and down and do this in time with your mouth going up and down or do the stroking up as your mouth descends.

Samantha was sitting upright now and asked: "If those are the basics of technique, what are the advanced techniques?"

I thought some more to organize my thoughts and plowed ahead: "First is the tongue. Know where and when to use it and where the sensitive spots are. Those include the head, the area where the head joins the shaft. Second thing to think about is pressure. Pressure is good. It helps simulate sex, so keep it up, but keep it lubricated. The only other thing to consider on the advanced side is your throat. Putting a cock in your throat is not easy. Many will gag or retch when they try. Guys, however, love it. It feels great due to pressure and penetration aspect of it. It also demonstrates commitment and devotion as guys understand that this must be hard. The last area to talk about is the finish when a guy cums. My advice is, love it. Spray it on your face, your breasts, or the best is probably just swallowing it. Don't be grossed out by it or spit it out. Guys will find this totally motivating."

Samantha was now looking a bit flushed in her chair as was Teena. Samantha asked: "Won't guys think I am a slut for eating cum?"

I said: "They might think you are a bit slutty, but that it isn't a bad thing. You have heard the saying: 'every man wants a chef in the kitchen, a lady in the living room, and a whore in the bedroom' Well, I generally concur with that. The other thing to think of is what you want. Most women want basically the same thing. Admitting your desires and mirroring your partner's desires is the way to achieve happiness and satisfaction. The other factor to consider is the oral sex that you want it back from him. You will probably want him to perform on you. If he is doing his job, he will get all your fluids in his mouth just like you did for him. Getting excited about oral sex will get him excited. If it doesn't, drop him like a hot potato. Life is too short for bad oral sex."

Samantha was now crossing her legs and had one hand in her lap. I wasn't doing much better as my erection was evident in my gym shorts. Samantha then asked: "Do you have any thoughts on performing oral sex?"

I thought again for a second and said: "I am less an expert on this, but I think that the most important thing to do is listen for nonverbal cues and maintain sole focus on her pleasure" I then laughed and said: "I bet your mom could tell you a lot" and gave Teena a wink. "My only other thought is to involve all the areas in the genital area."

Samantha said: "What do you mean by all the areas?"

I said: "Stimulation can occur in many areas. This includes a woman's clit, her thighs, her pussy lips, inside her vagina, her bum, and her asshole. Tongue, fingers, and adult toys can be used on all areas and he should think about lubrication."

Teena said: "Samantha, I agree with Ray on all of this. We can talk later about what a woman might want"

Samantha said: "Mom, we are getting answers, and this was your idea. Let's keep exploring. Ray, what can you tell me about regular sex?"

I said: "First off, there shouldn't be anything regular about it. Keep it fresh through different positions and locations. Determine the elements that get you off and communicate that."

Samantha asked: "So what positions do you like best?"

I said: "It depends on the person I am with and what they want at the time. A favorite is entering from behind while the woman is kneeling on the bed with her ass up. A second is when a woman is holding her legs up and wide and had her whole end extended. I also enjoy what they want as well. It might be riding on top or even missionary."

Samantha was clearly eager to learn and asked what else I did.

I said: "I will include kissing, the touching of breasts and the stimulation of nipples, touching or rubbing of the clitoral area, and some play around the anus"

Samantha said: "Ray, do you like anal sex?"

I paused and then responded: "Yes I do, but it takes preparation and patience. You generally need artificial lubrication and the woman had to prepare herself or it can be painful. Good hygiene is also strongly recommended prior to trying. Most women find it pleasurable, but you need to go slowly and be prepared."

Samantha was breathing deep, and I saw the hand in her lap press down. She was clearly turned on. She said, "Ray, thanks so much for this. This will make a difference with my next boyfriend and I really appreciate it. My only other question is how you know so much?"

"Samantha, it was a pleasure to talk, and I hope I enlightened you. I wish I had been able to communicate this with my daughter and son, but there was never the opportunity. Maybe Susie had that talk as we had learned together."

We all got up and went to the front door. Teena thanked me profusely and Samantha gave me a big hug which was a bit embarrassing as I am sure that she felt my erection on her leg. On the other side, I could feel her stiff nipples pressing into my chest.

The rest of the day was uneventful and filled with mundane chores around the house. Teena gave me a call at about seven pm. She first thanked me for being so candid with Samantha. I said that given what I knew of her earlier conversations, I hoped that my insights would help.

Teena added that Samantha kept asking questions to her about any advice she had. She said that she had added some pointers on what she liked when receiving oral and talked a bit about how size mattered. She added that Samantha made additional negative observations about Rick. Samantha even added that she understood that Teena might end it soon and she had said: "Mom, if you do end it, you should try to date Ray. He is a nice guy. And did you see the size of the dick in his shorts?"

Teena said she almost spat out her drink and just laughed.

Teena promised to visit me later in the week, possibly with Denise. She said that Denise might need a few days to rest.

That night, I woke up at about three am. I felt something on my bed and looked down to the foot of the bed where I could see the outline of woman. I raised my head a bit and said: "Samantha?"

She said: "Hi Ray. I am sorry for coming into your house and waking you up, but I wanted to talk some more and have been lying awake all night and had to see you. Your insights today were fantastic and opened my eyes to how great sex can possibly be. I tried to think of who I liked and was attracted to. I thought of my old boyfriend briefly but dismissed him quickly as he was a poor lover. I have other friends from high school or the neighborhood, but they are all so immature. I kept coming back to one person and that is you."

I thought and said: "Samantha, I know that what I said today was helpful and frankly, it probably got us all aroused. Don't fall for guys that just get you aroused, or you will get a negative reputation because there are lots of guys who will try to get you into bed with sexy talk."

Samantha said: "Ray, it wasn't the talk about sex. I will admit that it made me wet. It was when I thought of all my options and what I want is to learn from someone who is experienced. Someone who is caring and can listen. It is the reason we came over. I just want to get the real thing."

"Samantha, you are a beautiful young woman and are just starting your life. I may have experience, but I don't see how this could ever work out. It would destroy my friendship with your family, and I respect you and your family to do that to you or them."

"Ray, my family is heading for destruction anyways. I think my folks are at an impasse in their relationship and if that goes away, I want to make sure I have contact with you. You have always given me great advice and you care. Can you please consider this?"

Samantha reached out and touched my arm. I sat up and took her hand and said: "Samantha, I am sorry to hear about your family. I hope you and your mom always stay close. I think you are a wonderful person, but I can't do anything with you. Let me drive you home and then talk to your mother tomorrow. She has your best interests at heart and can help you best"

Samantha was sniffling a bit. I got up and pulled on shorts and t-shirt. I reached out and she took my hand. I drove her back home, largely in silence. "Let's talk tomorrow night. Promise me that you will talk to Teena. She will help you" I got out and gave her a hug and kiss on the cheek. She went back inside quietly with her head hung a bit. I felt bad for her and wondered if I had made the right choice sharing my thoughts on sex and relationships. She was a beautiful and special woman.

The next day was busy at work. I sent Teena text that we should discuss Samantha tonight. She sent me a text back in the early afternoon that we would talk tonight. I got home that evening and grabbed a quick meal. I was just cleaning up when the doorbell rang. I went to the door expecting just Teena, but she was accompanied by Samantha as well. They were both dressed very casually in t-shirts and gym shorts. I gave them both hugs and they came in. We went to the living room and they both sat on the couch and I sat in chair facing them.

Teena said: "Ray, Samantha and I had a real heart to heart about sex this morning. She shared with me what she did last night. I have to say that I never been prouder to call you my friend. You didn't take advantage of a vulnerable beautiful woman."

Samantha added: "I am sorry that I tried to seduce you last night. I was so excited about how you described sex yesterday and just wanted to experience that."

I said: "Ladies, you both mean so much to me and I don't want to jeopardize that. How did your discussion go today?"

Teena said: "We had a great talk about Samantha's desires. I have thought about it through the day and have concluded that you should have sex with her to show her how great it can be. I don't want her to make the mistake I made and settle for mediocre sex for years. She needs to see how good it can be. That will help her now and in the future. I trust you to be kind, gentle, and rough when you need to be. My last thought on this is that I think I should be here to help coach."

I was flabbergasted at Teena's suggestion. She wanted me to fuck and suck her only daughter. Wouldn't she be jealous? I thought it through and could see her logic. Teena clearly had no issue in sharing with me. I looked over to Samantha who was sitting next to her mother and holding her hand.

"Ray, you said that you couldn't do this last night and I understand and thank you for being such a gentleman. We are here to ask you to reconsider and to not be a gentleman tonight" Samantha said with a smile.

I got up and joined them on the couch so that I was next to Samantha. She was so young and lithe having been a competitive dancer. She was just a younger and slightly taller version of her mother. I leaned in for a kiss and she met me halfway for a passionate kiss. She then went to pull her shorts down. I stopped her by gently grabbing her hand and said that there was no rush. I stood back up and held my hand out to my ladies and said: "Let's go upstairs and have some fun."