Sex Lessons From Grandpa

"I don't know. I get really excited and it feels so good but when he collapses on top of me, I still want to keep going."

"Fair enough," I answer and then sit back in my chair considering what to say next.

"What? What are you thinking?" Sam asks.

"I don't think there is anything wrong with you," I answer. From what I've seen, everything is very right about her but I don't say that. "I think your boyfriend isn't experienced enough yet to get you off." I hold up my hand to stop her interruption. "There are a few things you can do about that."

"What things?"

"You can talk to him. He probably doesn't know. Tell him what you need and ask him if he'll try a few things to help you get off like he does." She's shaking her head before I even finish.

"You don't know him," she says. "He would feel like I'm putting him down and telling him he's not a good lover."

"He's not," I say before thinking about it.

"Trust me, that would not go over well," she says. "You said a few things. What else?"

"I have a feeling you're not going to like this one any better but you could go out with a guy who knows what he's doing and verify for yourself that it's not you."

"I can't go out on Rob! He's my boyfriend." Her head is swirling between Jenna and Sam like she's pleading with them to agree with her.

"Maybe Jenna would loan you her boyfriend just for a night so you can experience what she's getting." I don't really think this is a good idea but I say it just to get a rise out of Jenna.

"I got a better idea." Jenna says, looking right at me with that half smile of hers turning up her cheek bones and making her almond shaped eyes twinkle exotically. "Why don't you show her, Granddad? You're experienced and seem to know a lot about female orgasms."

I don't have a comeback for that. I'm sure my mouth is hanging open. I just stare at Jenna's defiant smile as she sits back and folds her arms across her ample chest. Touché. I smile at her like she just made the biggest joke ever but Sam's not laughing.

"That is a great idea!" Sam says excitedly as she sits forward and tries to gauge my reaction.

"It's a very bad idea," I say, not taking my eyes off Jenna.

"Why?" Sam asks.

"Because..." I pause momentarily, as my mind sorts through the myriad of reasons why I won't be giving Angie any orgasms. "I'm too old, too married and she should be fucking someone her own age."

"You just made a pretty strong case that guys her own age aren't able to give her what she needs," Jenna retorts. "You are obviously not too old to fuck," she continues while glancing at my crotch. I fight the urge to look down and see if my hard cock is really that obvious. "Besides it's not like you're going to marry her or anything. You'll be like a teacher or mentor or whatever."

"It's the whatever that bothers me," I respond.

"Do I have a say in this?" Angie asks quietly.

"There is nothing to have a say in because I'm not doing it!" I say, pushing my chair back and standing up. I'm about to make a dramatic exit when I notice the three of them staring at my crotch. This time I do look down and sure enough, the front of my shorts are tented straight out in front of me.

"Fine, I'm human. So sue me!" I say and make as dramatic an exit as I can, stomping off to my bedroom.

Flopping down on my bed, I feel really stupid for the way I handled that. But what the fuck was I supposed to do? Why would Jenna even suggest something like that. What would happen if Angie's parents ever found out? Or my wife? What the fuck is she thinking? And Sam thinking it's a great idea. What's that about? I'm staring at the ceiling when there's a knock on the door jam of the open door.

"Hey," Angie says. "Can I come in?"

"Sure." I sit up on the edge of the bed. "I'm sorry about all that. I'm sure they mean well," I say as Angie comes over and sits next to me.

"I understand why you got weirded out," Angie says with a nervous laugh. "But... um... would you at least think about it?" she asks. She's sitting right next to me and she turns sideways on the bed so she's facing me. "I'd really like to know for sure if something is wrong with me." He eyes are welling up with tears and I instinctively put my arm around her.

"There is nothing wrong with you, sweetheart." I tell her as I pull her against me. She's still in her bikini and I wasn't anticipating the warmth of her bare skin. My heart thumps in my chest as I will my cock not to react.

"You don't know that for sure," she says, leaning her head against my shoulder. Damn! Why am I arguing with her? Because she's an eighteen-year-old girl who just needs a better boyfriend!

"I'm pretty sure," I say. "And like Jenna said, I have some experience with this." I try for a lighter tone but instead I've spurred her on.

"That's why you would be so perfect," she says. "It wouldn't be like I'd be going out on my boyfriend... well at least, not with anyone at school who would tell everyone about it. And I'd really like to know for sure. Please! Just tell me you'll think about it."

With a heavy sigh, I relent. "I will think about it... but that's all... no promises, okay?"

"Okay!" Angie hugs me tightly and kisses me lightly on the cheek. "Thank you," she says and gets up to leave.

"Angie," I call her name as she gets to the door. Her bikini bottom has ridden up between her cheeks and I'm treated to a wonderful view of her near naked ass.

"You need to think about this, too," I tell her as she stops and turns towards me. She just smiles. "I'm serious, this shouldn't be a spur of the moment decision."

"I'll think about it, Granddad," she smiles. "It's probably all I'll think about." She disappears into the hallway.

Fuck! Most guys would kill to be in my position -- a beautiful young woman wants me to prove she can have orgasms. It's like the ultimate fantasy. So why am I feeling so desperate? Not desperate, I'm scared shitless. It's one thing to fantasize about my granddaughter's friends and jack off to a video of their naked bodies. It's something else to actually have sex with one of them.

When I finally emerge from my bedroom, they are out on the patio. Music is playing on one of their phones as Sam paints her toenails and Jenna braids Angie's hair. Such typical behavior makes me smile and I decide we should just have a fun afternoon.

"What do you guys want to do this afternoon?" I ask, walking onto the patio with a cold beer. They turn almost in unison, with big wide grins. "Besides that," I add and we all laugh.

"How about miniature golf?" Sam asks, looking from me to her companions for support.

"I like that," Jenna says, "since what we really want to do is off the table." She smiles that wonderfully lascivious smile again before turning her attention back to Angie's hair. My cock stirs and I wonder if I'd be as resistant if it were Jenna instead of Angie who wants me to fuck her. Probably, they're the same age but Jenna just seems more, I don't know, worldly than the other two, in both looks and actions.

"How about lunch at the pier and then miniature golf?" I ask, getting nods all around. Angie is the only one who hasn't actually spoken her ascent.

We have a wonderful afternoon. All three are really fun to be with and there is relatively no sexual tension between us. It helps that their shorts outfits are much less revealing than the bikinis I was used to seeing them wear. It is also clear from their playful teasing and the way they finish each other's sentences that they are very close friends and have been for a long time.

When we get home, I grill burgers and we eat outside. After dinner, they leave to sit on the beach until sunset and I call my wife. She says her sister is doing better but she won't be home for another week. I assure her that we are doing fine and that she doesn't need to worry about us. Or does she? I retreat to my bedroom to think.

The question is still looming out there and I haven't decided what to do about it. After having adamantly declined, I don't realize until just this moment that I'm actually considering it. She is a beautiful young woman with a problem I am certain I can solve. There is no question that her inexperienced boyfriend is the problem.

I lie down on my bed and try clearing my brain of the image of her sexy body so I can treat the decision objectively. Every time I mentally list the pros and cons the cons outweigh the pros by a huge proportion. The trouble is that my dick stays hard through the whole process, tipping the scales in favor of the pros. Fuck!

I hear Sam and her friends come back inside and the TV burst to life in the living room. I consider initiating another discussion to persuade them how illogical this is but decide avoidance is a better strategy. I stay in my room, trying to read my book. As you can imagine, my mind keeps wandering.

I'm just putting my book on the nightstand and turning off my light when the TV shuts off and I hear them make their way down the hall to their bedrooms. A light knock on my door and Sam sticks her head it.

"Goodnight, Grandpa," she whispers into the dark room

"No goodnight kiss?" I ask.

"I wasn't sure you were awake," she says as she makes her way to my bed and crawls up beside me.

"Just turned the light off," I answer, kissing the top of her head as she snuggles against me.

"I'm sorry about this morning," she says. "I didn't mean to put you in such an awkward position."

"No, I'm sorry," I respond. "I shouldn't have freaked out on you guys. My reaction was inappropriate. I should have stayed and talked it through some more."

"Only part of your reaction was inappropriate," she laughs, tickling my ribs. I'm glad she can't see me blushing in the dark thinking about my tented shorts.

"I'm sorry. I couldn't help that," I say, squirming away from her hand.

"At least we know you weren't repulsed by the idea," she laughs again before settling her head back down on my shoulder."

"Yeah, that was pretty obvious but you know this is wrong, don't you?" The length of her silence gives me my answer and I realize that the right and wrong argument isn't going to get any traction.

"It's just that Angie is so self conscious, you know?" Sam lets out a long sigh and leans up to look in my face. "She thinks because her boyfriend is inept that there is something wrong with her. Now you won't have sex with her so she thinks there's something wrong with her. Instead of helping her, we're just making it worse!" She blurts this all out in one breath and then plops back down. "I just want to help her," she whispers.

While I'm glad to hear that my granddaughter realizes that there is nothing wrong with Angie, I'm not sure how me fucking her is going to build her self-esteem. I choose my next words very carefully.

"Are there other examples of Angie having low self-esteem?" I ask. Sam thinks for a long time before answering.

"No. I think it's just with sex," she finally answers. "She's very confident in sports and she's really smart and graduated with honors." Sam takes a breath before continuing. "I know she doesn't like her body. She's always complaining that her breasts are too small and she's always afraid of losing her boyfriend to someone with a better body. That's why she won't talk to him about sex. She's afraid of losing him."

It occurs to me that this is probably typical coed dramatics and I wonder if Sam feels the same way.

"You two have similar bodies, you don't feel that way do you?"

"No, my breasts are a little larger," she says. "But even if they weren't I don't think my body defines who I am and I've tried to tell Angie that but..." her voice trails off and we're silent for a while.

"Will you at least consider helping her, Grandpa? I know you don't think it's right but is it right for her to feel rejected? And besides you could show her what a lousy fuck her boyfriend is, right?" She kisses me on the cheek and rolls over to get off the bed.

"You've given me a lot to think about Sam," I answer noncommittally.

"Don't take too long," she says. "We've only got tomorrow. Remember grandma said that Jenna and Angie's boyfriends can come down on Friday to join us for the weekend." I had forgotten that arrangement until just now.

"I'll have an answer in the morning, Sam." I assure her, wondering how I'm going to decide. "But don't get your hopes up."

"Like my teachers always tell me, don't over think it," Sam says with a big smile before leaving me alone with my thoughts.

I toss and turn all night as I consider the risks, not the least of which is my wife finding out. We've continued to have a very active sex life. We're not as flexible as we once were but we don't confine ourselves to the missionary position either. We have both always been addicted to oral sex. I'm not worried about whether I'll be able to give Angie several mind-blowing orgasms but I am worried about what they might say or tweet when this is over.

Sam and her friends usually sleep late but since I'm awake early, I run a few critical errands and I'm sitting at the table when they wander into the kitchen.

"I'll do it," I say without any preamble.

"Really?" Angie's face lights up and all three of them rush over to hug me.

"But we have to talk about a few things first." I motion them to the chairs and they take their seats, looking at me like they are about to hear the meaning of life.

"First, you asked me for confidentiality, Sam." She nods. "I have to ask you guys the same thing. No discussing, tweeting or anything else. When it's over, no one talks about it, agreed?" All three nod their ascent.

"Second..." I don't really have a second point. "Well, I guess that was the main thing but I want to talk about how we're going to do this," I say, looking at Angie. "How did you envision it? Will you and I just go into my bedroom while Sam and Jenna wait out here?"

"No way," Jenna answers for her. "We're all coming into the bedroom. We want to see what this is all about."

"That's alright isn't it?" Sam looks questioningly at me.

"I think that's up to Angie," I answer, not sure how I feel about an audience.

"I just assumed they'd be there," Angie says. "That makes it less like I'm cheating on my boyfriend and more like you're teaching us stuff." Her logic isn't infallible but if they all want to be there while I fuck their friend... damn! What have I gotten myself into?

"Okay. I've been thinking about this and we're not going to just plop down on the bed and start having sex. We're going to spend the day together and work towards it gradually, like you would in a real relationship, okay?"

"Whatever you say," Angie answers, obviously eager to get past the talking stage.

"You're the boss," Jenna adds. Sam just smiles appreciatively at me.

"Breakfast first and then we'll go in the pool," I announce. "I'll fix breakfast while you guys get your suits on."

They rush to the bedroom while I whip up some eggs and bacon. After the dishes are cleaned up we head out back to the pool. I don't have this all planned out but I know I want to start with a relatively normal setting and then gradually make it more erotic.

I grab a beach ball and we start tossing it around in the pool. I stay focused on Angie even though Jenna's bouncing breasts are terribly distracting. We're all having fun and after a good round of innocent splashing I gradually begin touching Angie in a more familiar manner. At first I'm just playfully grabbing her around the waist, pulling her against me and then patting her fanny as I push away. I progress to kissing her neck and telling her how beautiful she is while my hands wander over her exposed skin.

Sam and Jenna instinctively retreat to the other side of the pool with the beach ball and I turn Angie towards me. Brushing her hair from her eyes, I kiss her tenderly on the lips. My hands are lightly caressing her shoulders as her lips part and my tongue slides inside her warm mouth. She is a surprisingly good kisser and my hands roam her naked back as our tongues dance in and out of each other's mouth. Sam and Jenna have climbed out of the pool and are sunning themselves on the deck as they watch our increasingly intimate encounter.

Cupping Angie's firm ass cheeks, I pull her against me and my cock makes no secret of its arousal level. Damn if she doesn't surprise me again by wrapping her legs around me and grinding her bikini-covered pussy against the bulge in my suit. With our tongues continuing their tasty probe, I untie the strings holding her bikini top and slip it out from between us.

Angie halts the kiss, realizing she is topless in my backyard. Good, I was finally able to surprise her. It's fairly secluded back here and there isn't much chance anyone will see us but I have found that just the idea of being exposed outside tends to enhance the arousal.

"I'm going to lick the water drops from your naked breasts," I whisper, wanting to stimulate her thoughts as well as her body. Her only response is an audible sigh as she gives into her urgings and crushes her firm tits against my chest. "I can't wait to get my mouth around your incredible nipples," I add.

Unhooking her legs from behind me, I stand Angie back on her feet in the water. With my hands firmly on her waist, I smile at the sight of her lovely chest. It's even more enticing in person than on the video but my gawking is making her self-conscious and she moves her hands up toward her chest.

"Don't cover yourself," I plead, pulling her hands back down.

"They're not very big," she says quietly as her face blushes and she lets her arms drop to her sides.

"They're perfect," I counter. "Like a masterful work of art." Leaning forward, I start licking the beads of water from the valley between her mounds. This is unbelievable. My cock is rock hard as I lick up and down, gradually widening my path to include the inside curves of her tits. Angie rests her hands on my shoulders as I slowly swirl my tongue all around the contours of her pert breasts, consciously avoiding her puffy nipples.

"Hmmm," she breathes, grabbing the hair on the back of my head as I flick my tongue across one of her nipples. Without moving my mouth from her breast, I maneuver Angie towards the side of the pool. She's a petite young woman and I easily lift her up and place her bottom on the tiled edge. Positioning her legs on either side of me, I devour her exotic nipples.

Damn! I've never felt anything like these puffy tits. I'm used to more conventional nipples that jut out like Jenna's but these babies are amazing. The nipple and areola is just one big bulbous tip on her round breast. I suck the entire thing in my mouth, flicking my tongue across it and trying to distend the little bud that's buried in the middle.

"God, that feels good!" Angie moans as I knead her soft breasts with my hands and vigorously suck on the rounded tip. Her tits may be different but they are very sensitive. I squeeze more tightly around her breast as I continue sucking and a tiny bud emerges that I can grab with my teeth. Applying just enough pressure without actually biting, I pull her nipple away from the surrounding areola and suck it into my mouth.

"Oh fuck!" Angie cries, sliding forward on the tile and humping her horny pussy against my torso. I lightly chew on her taut nipple while continuing to maul her firm breasts with my hands.

Switching to her other tit and giving it the same treatment, I'm shocked by her incredible responsiveness. Her boyfriend must be a complete idiot not to be able to get her off.

Releasing her tits, I motion Sam and Jenna over while I untie the strings on the side of her bikini bottom. Angie surprises me by grabbing my head and pulling me into a kiss, rekindling the intensity of our earlier tongue swapping. Damn! She is hot to trot!