Dad sat in his office, enjoying his latest treasure. It seemed like every time he and mom left home, there was something interesting happening on their patio. Not that he was complaining. The hot tub action starring Lacey and her friend Tiffany was great. Tiffany needs to trim that dark bush of hers, though. But it was good enough that he had rubbed one out, even before he got to the end of the clip. He had a good start on his own private homegrown porn collection.
At Ricky's house, he and his mom had made love the night before. It began with mom in the bathtub, having a leisurely soak. Ricky knocked and asked to come into the bathroom with her. Mom was horny and ready. She eagerly told Ricky to come in. He had soaped her down and scrubbed her good and proper, all over her body. There were lots of kisses and Ricky worshiping her body. He just loved her breasts, her firm runner's ass, her long slender legs and her flat tummy. They moved to Ricky's bedroom where he had scented candles burning and soft music. He really knew how to set the mood for her. They spent a lot of time in bed with foreplay. When they finally got around to penetration, Ricky said that he wanted to try a rear entry. Mom confessed that it had been one of her favorite positions. Ricky was able to enjoy a view of her firm ass, her muscular back, and her pretty hair. As a bonus, he could lean down onto her back, reach around and cup a breast with each hand while he fucked. Mom's hand extended down underneath to work her own clit while Ricky stroked in and out with his dick. She easily came before Ricky did. He was getting much better at holding out and prolonging the experience.
This morning, mom left for work, telling Ricky again what a wonderful time she had the night before. They kissed like lovers as she left for work. Ricky gathered his school gear, getting ready to go to Lacey's house to escort her to school, when she surprised him by walking into the kitchen.
"Good morning, Ricky"
"Mornin' Lacey. This is a surprise. To what do I owe the honor?" Lacey lightly kissed Ricky on the lips and led him by the hand to the kitchen table. "Please sit down for a minute. I have something I want to ask you." They sat down and Ricky wondered what this was about. She seemed very serious.
Lacey began, "I have a request. Actually, it is for a friend of mine. Or actually a mutual friend of ours." She paused, her brow furrowed. Finally she said, "dammit, Ricky. I lay awake half the night trying to figure out how to ask you. I thought I had it figured out, but now in the light of day, I'm just not sure how to ask you."
Ricky laughed a good hearted laugh. "Lacey, don't forget that we are soul mates. You can ask me anything, no judgment."
Lacey smiled and took his hand. "Yeah, you're right, of course. So here's the deal. You know Tiffany, from school? She wants you to help her become a woman."
Ricky looked into her eyes and asked. "Are you asking what I think you are asking?" Lacey said, "Is this a terrible idea, Ricky?"
Ricky looked puzzled. "Wait. Are you asking me to fuck her and take her virginity?" Lacey looked down at her feet. "This is bad, isn't it? Tiffany and I kinda came up with the idea together. I told her that I would approach you to see if you would even consider it."
"No, Lacey. It's not bad. It's sweet that you are willing to share for the sake of a friend. It just caught me off guard. I never imagined that I would ever get a request like this. On top of that, you know that breaking a cherry is not something that I am particularly good at. Remember how I nearly spoiled it for you." Lacey looked up and smiled broadly, "Then you'll do it?" Ricky looked cautious, "The most important thing to me is not to spoil our relationship. I am a young guy. I could fuck most any girl, it's in my nature. We don't develop deep attachments to a woman, just because we have sex with her. Men are just different like that. But I don't want to do anything that could spoil our relationship."
Lacey looked serious now and said, "This would be a one-time thing, I want to be in the room when you do it and help. Rickey, I know that you love me above all and that our relationship would not be in jeopardy. I am asking you to do it and I solemnly promise that I will never hold it against you."
Ricky looked thoughtful. "This would need to be kept secret. It is not something that should be talked around. Tiffany would have to promise to never reveal who took her virginity. Do you really think she would be up to all of this? Does she really want me to do this?"
Lacey smiled and said, "Oh yes. She will forever worship you if you do this for her. She realizes that she is asking a lot of us. Tiffany came over last night to work on our math assignment. We talked about some of her problems and sort of came up with the idea together. I will have to tell you about what we were up to, sometime. It's a Juicy story that you will want to hear, but we don't have time right now. We need to be leaving for school."
Ricky said, "I want to sleep on it before I give an answer."
All morning in school, we saw Tiffany across the room. She would smile shyly, but she kept her distance. When she didn't show up for study hall, I got worried. "I better see if she is all right." I found her in the girl's bathroom, biting her nails. "There you are, girl, what's the matter?"
"Oh Lacey, I'm just worried sick! How is Ricky taking this? And how are you taking it? Please, don't hate me!"
"Woah, Tiffany, you need to calm down. Everything is alright. Nobody is going to hate you. Ricky is seriously considering your request, but it's complicated. You are asking a lot of him, you know."
Tiffany sighed, "Yeah, I know. I almost wish I hadn't said anything. I do want it badly, but I don't like to cause such trouble and you two are my friends."
"So, are you of the same mind about it? If Ricky comes to peace with it, do you still want to go through with him taking your virginity? "Lacey asked.
"Oh, yes, yes, yes. I want to be sexually liberated like you and Ricky are. By the way, thank you again for last night. And I love my new look; down there I mean." and we had a laugh.
"Well I know you are nervous and having a hard time facing Ricky, but the best thing you can do right now, is come sit down with us in study hall. And you should know that if this doesn't work out with Ricky, that you will still be our friend, and we will want to help you in any way we can." Tiffany threw her arms around me and began to cry. "Thank you so much, you are such a good friend."
"Alright now, you just wash your face, calm your nerves and come join us in the study hall. I'll let Ricky know you are coming."
Ricky looked up when he saw me coming back, "Did you find Tiffany?" I sat down at the table.
"Yeah, she is pretty tore up, just nervous to face us. I think she is alright now. I asked her to come join us."
"Good," Ricky said. "I would hate for this thing to ruin our friendship. Does she still want to go through with it?"
"Oh yes. She wants it very badly, but she needs to get over some of her nervousness. That's partly why I asked her to come join us. I hope we can help her get comfortable with us again."
Tiffany came into the room, and walked over to the table. Her body language said that she was terrified. She took little, shuffling steps, clutching her books to her chest with both hands, and her smile did not reach her eyes.
Ricky greeted her with a smile. "Hey, Tiff, glad to see you. Please join us." Ricky is my knight in shining armor. His deep, mellow voice and genuine smile will go a long way in making Tiffany feel loved and welcome. She immediately began to look more at ease. She pulled out a chair, set her books on the table, removed her jacket, and sat down. She didn't say anything, and I think she did not trust herself to speak.
Trying to break the ice, I said, "Math class is up next. Are you worried about it?" She looked up at me and smiled, "Oh no. After you helped me last night, the lights came on and I understand it now. You are such a good teacher, Lacey!" I smiled and winked, so she would know that I had caught the double meaning of her words.
"It's not hard when you have such an eager pupil," I replied and we both stifled a laugh, so I knew she caught it. Being more serious, I said, "I think you can overcome all of the challenges that you face. We all just need a little help, sometimes."
"Yeah. I guess I need quite a lot of help." Tiffany said.
Ricky chimed in, "Well we are here for you, Tiff. I am not certain to what extent I can help, yet. It is my belief that we should sleep over any big decision. At this point, I am not saying yes or no. But I am considering it."
"Oh thank you so much, Ricky. I am so grateful to you, whatever your decision I hope that we can remain friends, either way."
Ricky said, "Of course! If we decide to go through with it, there is one thing I will need from you, and that is your absolute promise to protect my identity. You must solemnly promise to never reveal what happened; ever. If you are ever asked, by a boyfriend, your parents, even a future husband, you must say that it was just a random guy and you can't say who it was. That is one condition that I cannot compromise on. Is that understood?"
"Yes, Ricky. Sure, I can understand that. You can trust me." We all smiled.
Trying to lighten the mood again, I asked, "Do you mind if I share with Ricky about our adventures yesterday evening at my house?"
Tiffany looked down and chuckled, "only the good parts, not the embarrassing moments." And we all laughed again. We shared the happenings of last evening, first me telling one detail, then Tiffany telling about something else that happened. We laughed a lot and it was a great ice breaker to be able to talk about the more intimate parts of our lives and even to share our foibles.
Too soon, study period was over. Tiffany said to Ricky, "Lacey has helped me out a lot, and there is still so much for me to learn. I hope you know how lucky you are to have such a great girl. Of course she is lucky to have such a great guy, too."
At home that night, Ricky wrestled with his decision. He was standing at the sink helping mom with the dishes. He really wanted to help Tiffany, and in one way it would not be hard to do. She is not nearly as pretty as Lacey, but she is a very sweet girl and not at all hard on the eyes, either. But he knew he did not want to think with his dick. There was the risk of feelings of Jealousy with Lacey, though she assured him that would not be a problem. And what about mother? How would she feel about him fucking Tiffany? Should he even tell her?
"You seem quiet this evening, Ricky," mom said, looking at him. "Something is bothering you. Do you want to talk about it?" Mom was alway so perceptive. You could never hide anything from her. Would it be wise to share this with her? One thing about mom, she is never judgemental.
"OK, so I do have kind of a tricky situation, and I am not sure what I should do. I have been wrestling with whether I should talk about it with you. The thing is, it does sort of affect you; indirectly, at least."
So Ricky told his mom all the details. By the time he finished, they were sitting on the couch in the den. "So what do you think? Should I consider helping Tiffany out?"
"You are right," mom said. "This is a tricky situation. For this to work, both you and Tiffany are going to need to be aroused and be into each other. You should have at least a little chemistry, which it sounds like you two might have. On the other hand, if you two finish with stronger feelings afterwards, Lacey is sure to notice and it could damage your relationship with her. She has promised not to let it affect her, but she will not be able to help it. And I think it is unrealistic to believe that you can have sex with Tiffany even once and it not affect your feelings towards her. It will also change the way Tiffany relates to you."
Ricky looked at mom and said, "It just doesn't sound like a good idea, does it? How would it make you feel, if I did it? I mean since we are lovers?"
Mom smiled and said, "my only concern is your happiness. I am not jealous about you doing a favor for a friend, not even a sexual favor. I am not worried about your love for me; I am your mother. As far as the sexual love, I don't think this arrangement with you and me is going to be permanent. For me, each day is a gift. I will enjoy it for as long as it lasts and as long as it works for both of us."
Mom continued, "It seems to me that helping Tiffany with her request is the right thing to do. It will be important to look at it that way, as doing her a favor or a kindness. But as you have recognized, it will be risky. You will need to follow your heart on this matter. I cannot tell you what to do. The fact that Lacey has had sexual relations with Tiffany may work in your favor. It should make it harder for Lacey to be jealous if she has been physically and emotionally involved with Tiffany, herself."
"Thanks, mom. As always, you are right. I think I need to somehow clear my mind of the matter, sleep over it and see how I feel in the morning. I just hope I can lay it all down and actually sleep tonight."
Mom smiled, "Now that is something that I could help you with. Are you willing to try a little Yoga? You need to do some mindful meditation to clear your head. It works wonders," She said.
Ricky rolled his eyes, "I guess I could try it. You have not led wrong before. When are you going to teach me some erotic tantric yoga?" Ricky grinned.
Meanwhile, I lay in bed, staring up at the ceiling wondering if Ricky will help Tiffany. If he doesn't do something for her, maybe I could offer to do it for her with the vibrator. I could run the battery down some so it is not too strong, and use it to get Tiffany aroused. Then, just before she cums, I could insert the vibrator all the way into her vagina. The vibrator is not quite as large as a man's dick, though. What if it just hurts her without breaking her cherry? And doing it with a vibrator seems cold and impersonal. Using a real dick would be so much better and would improve her level of experience. If I had a dick like Ricky, I know that I would help her. But I should not put too much pressure on him. Maybe I should try to find her a suitable boyfriend. But a new boyfriend would probably be clumsy. It might be better to get rid of her virginity and then get her a boyfriend. It might be easier to get her a boyfriend if she were more confident, sexually. After running through what seemed like a thousand scenarios, I finally drifted off into a deep sleep.
Meanwhile, Tiffany is laying awake late at night. She finally took some melatonin to help get to sleep, but it hasn't kicked in yet. She lay there with her hand between her legs. Running her fingers over her newly shaved pussy felt so different than it used to feel. She could not get over her new look. You could actually see her pussy, now with most of the hair removed! She thought about what Lacey had said about her pussy being a work of art. She liked that thought. Earlier in the evening, she tried masterbating on her own. "I believe I need some lube," she thought, "and maybe I need to invest in a 'monster vibrator', myself. She finally did have an orgasm, but she had to work at it a good while and it was not as good as the one Lacey had helped her with. Her mind kept thinking about Ricky while masterbating. That made her feel guilty; he is my friend, Lacey's guy. Eventually, the melatonin did its job and she drifted off to sleep, thinking about Ricky and what it would feel like to lay in his arms.
Ricky awoke in the morning and stretched, after a good night's sleep. He awakens with the answer clear in his mind. He is clear on what to tell Tiffany and Lacey.
Meanwhile, I awoke gradually with nothing in particular on my mind. As I stretched and yawned, the problem with Tiffany came to mind again. I just hope that Ricky decides to help her, but I must be careful to let him make his own decision and not pressure him in any way. That would be best for all of them.
Tiffany awoke with a start with one thought: today Ricky will make his decision! At least I think he will come to a decision today. He said he needed to sleep over it? right? "I sure hope he will do it for me, but I better not get my hopes up," she thought. A pleasant tingling sensation developed down in her pussy as she thought about it. If he agreed to fuck me, when and where would they do it? What if she got pregnant? Maybe he thinks that I am on the pill? Could she even get pregnant, doing it the first time?
Ricky's mom stood at the stove, stirring oatmeal when he came out of his bedroom. "Morning, mom." He kissed her on the cheek.
Mom turned to Ricky and smiled, "You look well rested and happy this morning. You must have come to a decision that you feel good about."
Ricky replied, "I will probably do the favor for her. When I think about how it might go for her otherwise, with some random guy. Well I just think that a friend will do a better job. I think it will be important to talk about the risks with Lacey and then with Tiffany. I think communication will be key."
"I am so proud of you, Ricky. That is a very mature way to look at it. We make ourselves happy when we focus on the needs of others. You have done very well with that, even looking out for the needs of your dear old mommy." And she put an arm around my shoulder and squeezed me.
Mom turned to finish preparing her lunch to take to work and asked, "You don't have to answer if I am being too nosey, but do you know when and where yet?"
"Not for sure," I replied. "But I'm thinking the sooner the better, before any of us begins to over think this thing or loose sleep."
"Sounds good. If you decide to do it in our house, that will be fine. Just leave the porch light on and I will know to go away and give you guys some privacy," mom offered.
"That is very considerate of you, mother. Thank you."
I walked into the kitchen door to Ricky's house. "Good morning, Lacey. I hate to be rude, but I was just on my way out the door to work. I am running a bit late this morning." She gave Ricky a kiss on the cheek on her way out the door.
"Have you made your decision, Ricky?" I got straight to the point.
"I am inclined to do our friend Tiffany the favor. Just a few issues that we need to iron out."
I beamed a huge smile. I couldn't help it. "What are your concerns," I asked, getting serious.
"First, I want you to rethink your idea about being with us when we do it. I want to leave the decision in your hands. Let me explain. In order for me to function, from a physical standpoint, I am going to need to be aroused. Despite what some girls think, boys are not machines that can produce a boner on demand. There is going to need to be some foreplay. And if this is going to be a positive experience for Tiffany, there is going to need to be some passion involved. Is that going to be hard for you to watch?" As Ricky stopped speaking, I was stunned into silence.
"You are right, Ricky. I had not thought of that. I had envisioned me helping Tiffany to be aroused and coaching her on what to do. I also thought it would help prevent jealousy if I was present, almost as a chaperone. Thinking objectively, now, it could backfire on me. I don't know. It might still work, as long as I go into this with the knowledge of this new perspective. I need to think about it a bit."
Ricky smiled, "That's all I am asking. I think you need to be the one to make the decision. Just remember. We are soul mates. Whatever happens between Tiffany and I will never change that."
I ran over to Ricky and threw my arms around him, hugging him tight to me. "You are just the best, my love." We kissed, briefly. "We better get going to school, or we will be late," I said. "When do we break the news to Tiffany?"
"Why don't you break the news to her as soon as you can when we get to school. Then ask her to meet with us at study period to work out the details."
"Sounds good to me." With that we hurried off to school. I was quiet all the way to school, mulling over what Ricky had said about me being present. I could see Ricky's point, but I could see advantages and disadvantages either way. This is a hard decision.
We got to school in good time, and coming in the door I spied Tiffany down the hall, watching us nervously. Her expression fell as she saw that Ricky and I wore pretty sober expressions. She was probably trying to get a reading on us before we faced her. I probably appeared pretty sober, since I was trying to decide where I fit in this little party we were planning. "I see Tiffany," I said to Ricky. "I'm going to talk to her. She looks like she has been tortured."
I hurried down the hall and nearly had to run. Tiffany had turned and was moving down the hall away from me, her head down. Nearly catching up to her, I called, "Tiffany, wait up. I have some good news for you." At that she stopped and turned with a shocked expression on her face. We continued to walk slowly down the hall, our heads together so I could speak confidentially with her. "Ricky will do it," I said. He will fuck you and make you a woman." Tiffany squealed and gave me a hug.
"Oh thank you, thank you, thank you," She gushed. "You can never know what this means to me. When are we going to, you know, do it?"
"Don't know, for sure. We haven't talked about that. I don't think we want to wait long," I said. "There is another issue related to all this that I need your honest opinion on," I continued, more serious now. "One of my conditions was that I be present when you and Ricky do this together. I am having second thoughts about it. Please tell me your thoughts on this."
Tiffany looked like she was unsure what to say. "Well, do you want to be there?" She asked.
"That's inmaterial," I said. "I need to know your thoughts. How you really feel about it."
She thought for a bit before answering. "Well, I trust Ricky, not to do anything wrong to me or to hurt me. At least not any more than he has to," she smiled, a little embarrassed. "In a way, it made me feel a little embarrassed to think of fucking your boyfriend, right under your nose. But I don't mind you being there and would be happy to have you. It would not be a problem," She added, hurriedly.
Lacey replied. "That gives me the answer that I needed." I smiled and looked into her eyes. "I want you to have Ricky all to yourself when you two are together!" I said. I really felt good with my decision. I trusted Ricky completely. Our relationship is not worth having if we cannot trust each other. "Look," I went on "Let's work out some of the details during study period."
I found Ricky and explained my decision. "I think you and Tiffany will be more relaxed and free if I am not in the room standing over you. I am so glad that you brought it up. It took some work to find out how Tiffany really feels, but I think she will feel more free knowing that I will not be present standing over her."
Ricky smiled, "I am proud that you put Tiffany's experience ahead of your own worries. That is how I came to peace with this issue. I want to do what is best for Tiffany. You don't need to worry about me. I will always love you, no matter how things turn out in the bedroom with Tiffany. you are my soulmate."
Every time my gaze fell on Tiffany during morning classes, she was grinning like a little girl on Christmas morning. It felt really good to see my friend so happy. I sure hoped it would turn out well. Ricky looked settled, but like a guy with a weight of responsibility resting on his shoulders.
At study period, we met at our customary table and spoke together quietly. Tiffany was as happy as a new bride, and could not quit smiling. After some pleasant chit chat, Ricky turned to Tiffany and got down to business. "Lacey told you that I have agreed to help you out? I guess you remember my requirement for anonymity? Is that going to be a problem?"
"Not at all, Ricky. You have my solemn promise to never reveal what we do, beyond us three here." Tiffany said. "And thank you so much for what you are doing for me. You can't imagine what this means to me!" Tiffany was almost in tears as she spoke.
Ricky nodded and continued. "I want this to be a passionate and meaningful experience for you. You understand that while I may exhibit passion, my real love still belongs to Lacey. When we are done, there will be no expectation of further intimacy. Do you understand?" Tiffany nodded understanding, not trusting herself to speak. "When do you want to do this?" Ricky asked.
"That is completely up to you," she said. "The sooner the better as far as I'm concerned."
"I think, too, it would be better if we don't wait long. How about this afternoon? At my house? Mom won't be home and we will have the place to ourselves." Ricky said.
Tiffany blushed and said, "That would be fantastic!" Thinking a moment, she said "I can go home with Lacey from school to "study", and she can take me over to your house. I can arrange for my sister to pick me up again at Lacey's house."
I added, "you can eat dinner with me, and go home later in the evening." We all smiled and nodded. "Good. Tiffany, did you do your homework?" I asked.
She looked a little puzzled, "Well, I don't know. I didn't think we had anything due today?"
I laughed, "don't you remember the homework assignment that I gave you?"
She blushed and said, "Oh yeah, that. Actually I did. The masterbating didn't go too well. I did have an orgasm, but it took a long time and it was not as satisfying as the one you gave me. I couldn't find a single crayon around my house that wasn't broken. So I got a hot dog out of the refrigerator." We laughed as the image formed, unbidden, of Tiffany inserting a hot dog into her pussy. "I should have warmed it up in the microwave, first." and we laughed again. "I was afraid that it would break off in my pussy, when I clinched. Then what on earth would I do? Can you imagine me in the emergency room to have a piece of hot dog removed from my virgin pussy?" Our laughing was almost out of control, and we drew looks from other students.
I changed the subject. "Tiffany, have you ever seen a real man's dick?"
She looked down, shyly. "No, not really. Only boys getting their diaper changed. Only the pictures in our health book."
I smiled, thinking of the shock that was ahead of her. "You might want to prepare yourself. It is probably going to be bigger than you imagine. At least that was my experience. They start off pretty small, but it will grow up to three times in length with a full on bonner." Tiffany looked sober, now, trying to imagine. "Ricky is average size, but I have seen much larger." Ricky perked up and looked at me, quizzically. "Sorry, Ricky. I never told you about my uncle Steve. We'll save that for another time. Just be ready for something a lot bigger than what you might imagine. Ricky's sausage is a lot bigger than that little hot dog."