sped up a bit, but it only took a few strokes until I started cumming I her bowels. This sent Teena off and her muscle contractions were squeezing all the cum out of me.
After she (and I) relaxed for about 30 seconds, I pulled out of her ass. Teena moved up Denise again to get the dildo out. However, this time she didn't stop with the dildo falling out kept moving up to Denise's head where she put a knee on either side of her head and lowered her pussy onto Denise's mouth. She then did the nasty thing and sat up and moved at bit further up so that Denise was now licking her distended gaping cum covered asshole. I could see a dribble of cum coming from ass and Denise just licked it up and ate it.
I said: "Well clearly Denise got her dessert." She just looked over and licked her lips and smiled. The lesbian frat was going to be surprised with the nattiness of their new recruit. Teena reached over and pulled my cock to her mouth and cleaned me off.
The video had stopped, and we disentangled and sat on couch in our original positions. I kissed both ladies and said how fun that was. I then kneeled on the floor in front of Denise and helped her remove the strap on.
I said: I never did get my dessert and then gently pushed open Denise's legs and put my mouth on her wet pussy. I did long licks from her rosebud to her clit. I then added finger in her ass and one in her pussy and focused on her clit with my tongue. Teena had scooched over to watch, and fondled Denise's round breast and she had her orgasm, and I got my dessert.
Chapter 4:
Teena was going to come over to my place on Saturday afternoon. Rick was away, but she had to have a talk with Samantha on Friday night.
Work on Thursday was tiring after our Wednesday session. A couple of colleagues noticed but I didn't make any comments as I didn't want to kiss and tell. I did get back to doing my work outs at the gym and while there I picked up some tight-fitting spandex shorts and spandex jammer swimsuit. If my new dress pants were getting noticed at the office, the new shorts would help at the gym.
On Saturday, I cleaned up around the house and took care of the pool in my backyard. I was in swimming after cleaning when Teena came by for a visit. She was wearing a short summer dress which showed off her beautiful long blonde hair and lithe figure. She had let herself in as I rarely locked my door. I came to the side of the pool and looked up and greeted her getting a brief view of some white underwear under her dress. I jumped out and toweled off the wetness.
Teena looked on with a bit of hunger and commented on the new swimsuit. She said: "Ray, if you would have worn that to my pool party, you would have had wives lining up around the block to see you."
I added that it might be a bit larger right now that she had arrived.
I made us both gin and tonics and we sat out on the patio under an umbrella. I asked her how it had gone with Samantha. She rolled her eyes and said she didn't know where to start on that. I waited patiently, and she started to recount her interaction which started on Friday at dinner. Teena had started asking about the breakup with her boyfriend which Samantha said was fine. The boyfriend was not very attentive to Samantha and was always ditching her so he could hang with friends. This sounded like her dad who was doing exactly that, this week. As Teena said to Samantha: "No loss there."
Teena then broached the subject of her missing toy. She said that Samantha blushed and stuttered on this. Teena said that she reached out and made it clear that she was ok with it and wasn't offended. She made it clear to Samantha that she wanted to make sure that she had a healthy sex life and that she could confide in her with any questions or problems.
With this Samantha had calmed down and she then started opening up about her sex life with her boyfriend. She had been having sex a with him for a while but had found it unsatisfying. Samantha described to Teena how her former boyfriend wanted blow jobs but was hesitant to perform oral on her. Her sole time achieving orgasm with him was when he went down on her and he was disgusted with the fluids that came out of her after she had gotten off. The intercourse was short and after he got off, he just rolled away.
Teena felt bad for Samantha. She consoled her about the bad experience and then moved on to ask about the dildo. Samantha had said she had discovered Teena's box of toys last summer when she was in Teena's closet to borrow a blouse. When she had seen them, she didn't know what to say and just kept her discovery a secret. Samantha said that even before her breakup, she had been looking in the toy box and had tried a few of them.
Teena asked her why she had chosen the red one.
Samantha had said that she had tried a smaller one, but the red one which was about seven inches was more satisfying.
Teena said that she laughed at this comment and said people will say size doesn't matter but those are observations made by those who haven't experienced a big cock. Teena said: "I may have been a bit too revealing on that comment because Samantha who was getting more comfortable started to ask me some uncomfortable questions."
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."
Samantha literally jumped up with a huge grin. Teena had a wicked smile and said: "Samantha, get ready to have your world rocked" Samantha literally squealed and bounded up the stairs ahead of us. Teena leaned in and whispered: "She doesn't know yet that we are intimate, but it might come out tonight."
We got up to my bedroom and Sam was sitting on the edge of the bed facing us as we came in. I took a seat next to her while Teena sat in my dressing chair.
I leaned in for another kiss with one hand on her hip and other caressing her cheek. She said after the kiss that she wanted to do it all. I kissed again and moved my hand from her face to her hip and touched her side under her t-shirt. Her skin was smooth and felt that she had a lacy bra on. We lay back on the bed and I moved my hand to her stomach and slowly moved my hand to her breast which were covered with a very thin material. Her nipples were puffy with harder nubs on top.
At the same time, Samantha's hands were roaming over my chest under my shirt. Her hand then grazed my cock which jumped at the touch. She smiled and then grasped me through my shorts and said: "Oh my god. Is that as big as I think it is?"
I gave a shrug and lifted her t-shirt up to reveal a see-through black bra. I then ran my hand down below her hip on the outside of her leg. I moved up and then pulled down her shorts revealing matching black panties.
Samantha was undoing the button and zipper on my shorts, intent on wanting to see the monster. I raised my hips and she pulled down both my shorts and underwear together.
I glanced over to see Teena sitting in the chair with one hand under her t-shirt. She gave me a wink to send me back to Samantha. I was able to get the clasp off her bra and removed it to expose her firm breasts topped with pink puffy nipples. Sam reached out to grasp my cock and I leaned in to lick and suck on one of her breasts. I could feel her giving me a few preliminary strokes. I then moved to her mouth and kissed her again. After the kiss, she moved her head down my chest and gave my cock a close-up stare and she took it in from different angles.
Teena spoke up and said: "Wow, that is impressive. Sam, you know what you should do."
Sam gave me a lick along the length of my shaft and then engulfed my head. At the same time, she grasped on with both hands and started to pump me into her mouth.
I groaned my appreciation as I unbuttoned my shirt and squirmed out of it. Sam was looking up at me as she started to move her mouth up and down in time with her pumps. As she increased the amplitude of her head movements, she removed one hand to try and take more of my cock in her mouth. I could feel the head of my cock now touching the back of her mouth. She looked up again and then tried to push me into her throat. I felt my head get past her tonsils, but she then pulled back coughing.
I reached down and drew her up to me and moved my head down her chest giving each nipple a suck as I moved by. I scooched down to the end of the bed and reached up and removed her panties to reveal a mostly shaved pussy with a little patch of pubic hair above her slit. I put my hands between her legs and ran my hands on the insides of her legs. Slowly I parted her legs which were bent at the knee as she laid on her back. Teena came over and put a pillow behind Sam's head so she could have a view of what I was going to do. I ran first my hands and then my mouth down her thighs and gave her a kiss just above her pussy. She had a little shiver of anticipation. I extended my tongue flat and then moved my mouth down one pussy lip and then up the other. Samantha was squirming a bit to try and get me to put my mouth into her pussy. I then gave her a quick dart into her folds. She tasted sweat. I withdrew my mouth and moved my hands to spread her pussy open. I took a deep, slow lick starting at her rosebud up to her clit. Sam was openly moaning now. I took a finger and entered her tight pussy to the second knuckle. Sam moaned again and was squirming more. She was very close. I pulled my mouth back and removed my finger to lick it and lubricate it and then re-enter her a bit deeper this time. Concentrated my licking on her clit while hooking my finger upwards. This sent her off and she started to spasm on my finger and there was a rush of fluids.
I looked up at her and she said: "That was incredible".
Teena spoke: "I know you think that was great and it I know it was. The best is yet to come when he enters you"
I moved up next to Samantha and gave her a kiss. She was hesitant at first as my face still had her moisture on it. In the end, she got over it and responded passionately. She reached down and grasped my member. Samantha started to make a move to go down on me again, but I held her up and said: "I am ready and want to be in you. Is there a position you prefer?"
She said: "No one has ever asked. If I must choose, I want you to be in control. I would also love to see you as you go in."
Teena came over to the bed and said: "Scooch your bum to the end of the bed and then pull your legs up and apart. Ray can then stand at the end of bed and fill your wide-open pussy."
Samantha quickly moved. When she pulled back her legs, she demonstrated her flexibility from dancing by putting her legs behind her arms. She was spread wide with her bum slightly elevated off the bed. It was a beautiful sexy sight.
I came around the bed and leaned in for a kiss while moving my hand over her open pussy. I then moved down her body and couldn't resist giving her a quick lick from her ass to her clit. She shivered again. I then stood up and put the head of my cock just between her soft pussy lips and moved it up and down. Samantha was squirming and moaning, so I put it at the entrance to her hole and gave a little push. It didn't immediately go in and she moaned in frustration.
Samantha, then spoke up: "Ray, I am not a virgin and have had a pretty big dildo in there multiple times this week. You are a sweet and loving person, but I need you to put that monster in me. Don't be gentle and don't stop unless I say stop."
Samantha was right, I was being overly gentle. I held my cock at her entrance and started to push. The head went and I just paused briefly and kept pushing. Teena was kneeling next to Samantha and exclaimed: "Look at you taking that cock sweetie. It is spreading you wide"
Samantha was moaning and breathing in gasps saying that she was so full.
I made it almost all the way in and then touched the end of her tunnel. Samantha must have felt it too and it started her second orgasm of the night. It felt incredible as she contracted around me, and I paused to let her spasms pass. As they passed, I pulled back and then moved forcefully forward to bottom out in her pussy. This kept up for about five minutes with me steadily increasing my pace. I was getting close. Samantha was moaning and let out a little squeal each time I touched her cervix.
Teena said: "Ray is getting close, and I think you should do something special for him. I want him to pull out of you and for you to take him in your mouth for the finish. You will need to swallow it all."
I gave Teena a smile for her dirty plan and kept stroking into Samantha.
Teena reached in and gave Samantha's nipple a twist which then set her off again. I concentrated on baseball to avoid cumming while she spasmed. As it passed, I pulled out and Samantha immediately slid down the bed and put my cock in her mouth. Teena reached in and stroked me as I started to cum into her daughter's mouth. She gulped once and then ran her tongue over my slit to get the last out. She gulped one more time and then looked up with a smile at Teena and me.
I ran a hand through her hair and said how special that was.
We moved up the bed and lied down on our backs with me in the middle. Samantha was running her hand over my chest and I asked her about what she thought.
She paused and collected her thoughts and said: "Ray, that was better than I even imagined. You made me cum three times. That is triple the number of orgasms that I have ever had from sex. Cumming in my mouth and swallowing it was so dirty but felt so right if it enhanced your pleasure. I was a bit hesitant to kiss you after you had my juices on your lips, but I clearly got over that when I sucked you at the end. Mom, thanks for the advice and your dirty suggestions. My big disappointment was not being able to get you into my throat. I want to do it as it seems so sexy, but I think I need practice."
Teena said: "You need to practice on Mr. Red and reduce your gag reflex. The other way to start is to push him down before he is completely hard. It is a sure way to get him hard again."
Samantha gave her mom a look but didn't say anything. I think she was realizing that her mom had been up doing more than just using toys.
Samantha put her head on my chest and her hand had now drifted down to slowly stroke my cock. She spoke up and said: "Does the monster actually fit into a woman's ass? I know you talked about it. When I see it live, I just can't imagine it fitting."
I said: "It goes in but takes some practice and lubrication"
Samantha asked: "Are you going to try and put it in my ass?"
I said: "Only if you want me to. I don't think that will be tonight as I doubt that you are ready"
"I have had a finger up there and want to put one of mom's toys there, but they don't compare to this," as she gave my cock another stroke. She added: "I bet mom might be able to do it. She has a lot of toys for anal. What do you think mom?" She looked back at her mom after giving my head a quick lick.
"Samantha, tonight is about you and your pleasure and learning," Teena said.
"But mom, it would be about learning to see it happen. It is clearly something you are both into and sharing with you would be special."
"I don't know Samantha"
Samantha smiled as she hadn't gotten an outright refusal. She turned her head back and started licking and then sucking me while pumping her hand up and down.
I reached out and pulled Samantha's waist to me and she got the idea and straddled my face. I ran my hands over her lower back and reached down to touch her firm breasts as she resumed sucking me. I then moved my hands back over her skinny ass and pulled my mouth up to her red pussy lips and started licking. With one hand, I started putting my finger on her ass. I looked over at Teena and gave my night stand a stare.
Teena got the silent message and opened my nightstand drawer and pulled up the bottle of lube that was there. She opened the cap and squirted some in Samantha's crack. Samantha quickly looked around to see what her mother was doing. She just pulled up her legs a bit more which pushed out her ass a bit more.
I got my finger coated in lube and gently pushed it into Samantha's asshole as I was licking her. She grunted and started cumming as I pushed on her prostate. She lifted her head off my cock and yelled: "that is so dirty, and I love it! Mom, get those damn shorts off. I want to see him sodomize you!"
Teena didn't need any more coaxing. She got off the bed and said: "OK, I will show you how to be an ass slut. The things I do for you!" She pulled down her shorts and panties which matched the panties Samantha had on.
Samantha dismounted me and I rolled to the side as Teena got in her knees where I was laying and put her chest to bed which extended her ass in the air. Samantha and I kneeled on both sides of her mother as I put lube on the crack of her ass. I first put a finger in and then another.
Samantha squealed and said: "Mom, he already has two fingers in you"
I crawled around behind Teena and Samantha grabbed my cock to aim it at her mother's ass. I put some lube on my cock and Samantha rubbed it on.
Samantha looked at me and said: "Do it Ray. Put that monster in there. Ream her slutty shit hole. I know you have done it before, but I want to be witness to this."
I said to Samantha: "Spread her cheeks and get a good view so you know what to expect next weekend when I take your anal cherry."
I pushed hard into Teena as I knew she was prepared and loved it. Samantha's jaw was agape as I went all the way in on one push" I moved in and out a few times and then Teena screamed that she was cumming. She felt fantastic and it was so exciting to have her daughter watching with enthusiasm. I just kept moving in and out.
Samantha said: "Keep going Ray. She is a dirty anal whore and wants it all. By next weekend, you should be able to say, 'like mother, like daughter.' Are you getting close?" she looked at me with hunger. I nodded. She then added, "Pull out and paint my face with your load. I will show what a cum slut I am and won't dodge or flinch"
That sent me off and I pulled out and held my cock and pointed it at Samantha's face. As I pulled out, she opened her mouth wide and stuck out her tongue for a target. The fist stream went from her chin to her forehead. The next hit her nose and upper lip. She then closed the gap and sucked me into her mouth.
Teena looked at her daughter with awe and after Samantha took her lips from my cock, Teena used her fingers to push the cum on her daughter's face into her mouth. She then said: "Well, that was an incredible mother/daughter bonding experience"
Samantha said: "Mom, I get the distinct feeling that you have done this before. You didn't flinch when taking the monster in your ass. I don't think that this is due to just your self-help toys. I think that you have been fucking Ray for a while. If we are going to continue with Ray, and I really, really, want to, you have to be honest with me."
Teena looked sheepishly at her daughter and said: "There is a lot to share. You are right about Ray, but don't blame him. Denise snared him into his first date after our pool party a few weeks ago. After she had him once, she lured him back by promising him every guy's fantasy which is threesome with two women. She convinced me to be the third woman. As I have mentioned, I have been very frustrated with Rick for years. My only reason for remaining in the relationship was your wellbeing in a stable family environment. I was looking to end my marriage after you left for college in the fall. My timeline for ending it with Rick looks like it has moved up if you know all this."
Samantha asked: "Mom, tell me more about Denise. How did she convince you? I hope she didn't blackmail you or force you."
"Denise didn't force me into anything I didn't already want. We had been talking for a year about our frustrations. She was one who gave me the original box of toys that I have shamelessly added to."
Samantha asked: "Did she give you the strap on or did you buy that? How do you use it? I don't buy your description of a package purchase."
Denise had the sheepish look return and said: "At first, Denise shared the toys. This then led a lot of talk about masturbation. Eventually it led to mutual masturbation and finally we started fooling around together as she couldn't find any men that were adequate. The strap on was so I could fuck her."
Samantha was agape at this. She was deep in thought for a few moments and smiled. She said: "Wow, this is weekend of revelations. I thought I was doing all the sharing about boys and relationships. Now I find out that my mom is a bisexual anal loving big cock slut." She then reached out and gave Teena warm loving hug.
Teena came away with tears of joy in her eyes. I almost laughed thinking that being called a bisexual anal loving big cock slut could be a term of endearment. Who knew?
Samantha looked at me and asked: "So, how do want to proceed? You clearly have your pick of women in the neighborhood and if you walk around in tight pants, I bet you choices will widen even further.
"Since I went to that pool party, my life has transformed. I hadn't had any meaningful social life for the past few years. Susie got sick, we dealt with her passing, and the kids have all left home for college. Since that pool party, I have had the wildest sex I could imagine with multiple people and many times with multiple women at the same time. It is both exhausting and exhilarating. I don't know what my plan is, but I know that I have loved getting close with both of you."
Teena and Samantha both got dressed (Teena still had her t-shirt on) and had to head back to their place. I slept on one side of the bed to avoid the wet spots in the middle.