Road Trip Ch. 09

"That would be wonderful; all we could hope for," she replied.

"So, would you be willing for me to be in the room when it happened and give you both advice as it happened?"

"You mean, you'd see us both naked and fucking?" she asked, seemingly highly embarrassed even by the thought.

"Yes, in the same room, assisting and guiding. You wouldn't need to be naked, although that would certainly help."

She'd had a few seconds to consider the option and my suggestion that they could be at least partly covered seemed to put paid to the possibility that I was simply a voyeur wanting some kicks. She smiled for the first time since I arrived and turned to her parents. "Would that be Ok?" she asked.

"Up to you, sweetheart, we only want what's best for you," replied Peggy, probably softening her position a little.

"That sounds like a great idea," added David, "Why don't you give Rick a call and see what he thinks?"

Olivia remained seated for a few minutes in silence as we all awaited her decision. Then she moved to the buffet, picked up her mobile and called Rick. She went to the kitchen where she was obviously talking, then returned after a while to the lounge holding the phone against her clothing to muffle the sound.

"He agrees if you think it's Ok," she said to her parents. "He's free right now and can come around in a few minutes if it's all Ok."

David and Peggy looked at each other, then at me. "Is that Ok with you?" asked David.

"Yes, it's fine with me."

"Ok, Olivia, tell him to come around."

The doorbell rang a few minutes later and Olivia rushed to the door and let Rick in. They were obviously embracing in the hallway because it took several minutes before Olivia escorted Rick into the room and introduced him to me. As we shook hands, I sized him up; tall, reasonably well-built without being chubby, he looked quite athletic and from the way he was still holding hands with Olivia, I think he was as smitten with her and she was with him. After a short time of exchanging pleasantries, he came to the nitty gritty.

"So, you're going to watch us fuck for the first time," he said to me.

"Let's put it a little more correctly," I replied, "If you both agree, I'll be in the room with you when you first make love sexually to each other and lose your virginities to each other. To do this, I will need to watch what you're doing; I can't really stand with my back to you and give you guidance. So, yes, putting it crudely, I guess you're right."

"Ok, sorry," he replied, less aggressively, smiling, "It's just that this is all so embarrassing. It's bad enough for people to know we're doing it for the first time without having someone watching. But I fully understand and I really do thank you for coming up with the suggestion. I'm willing to go ahead if Olivia is also."

I looked at Olivia and after a few seconds she smiled at me and nodded, adding: "Yes, I'm willing for you to be in the room when we lose our virginities to each other," she agreed.

I looked at David and Peggy, who were now both smiling, and raised my eyebrows in an unspoken question.

"The bedroom on the right at the top of the stairs," said David with a grin. "Have fun, guys."

"Enjoy yourselves," added Peggy.

Rick and Olivia went upstairs holding hands while I followed a few steps behind them. I closed the door and sat in a chair while the lovers sat on the large bed. As expected, the bedroom was far larger and tidier than the average room for a teenage girl, due, no doubt, to an element of perfectionism that the parents had seemingly successfully transferred to their daughter.

"So, what now." asked Olivia.

"Have you been in bed together before?" I asked.

"Oh, yes, many times," replied Olivia. "We would have loved to make love together but the strong morality of our families prevented that."

"Well, now you'll be able to do that with your families' blessings. So, pretend I'm not here; what would you do? Don't answer, just go ahead and do it. When you get to the sexual part, I may offer you advice, if that's Ok."

They turned towards one another and kissed, their arms around each other as they allowed themselves to topple sideways onto the bed. They made out for around ten minutes or more, their hands exploring each other's body as they unfastened buttons and zippers to obtain better access to sensitive parts. Eventually they were both nearly naked, having seemingly lost their previous embarrassment, Rick was nibbling on Olivia's nipples while she massaged his rampant cock through his underpants. Rick moved his hand down to her panties, massaging her pussy through the thin fabric at first, then sliding his hand inside as he slid his finger between her obviously wet lips. She responded immediately with a low moan, moving her hand inside his underpants to fondle his cock directly. I must admit that watching their loving foreplay caused my own cock to become rock hard. Suddenly, Olivia lifted her head and looked at me.

"This is as far as we've gone before, what do we do now?"

"So, neither of you have masturbated the other to orgasm?"

"No, we thought that was as bad as making love."

"Ok, so let's do that first. Olivia, I want you to masturbate Rick to orgasm first. So, remove his underpants completely and begin stroking his cock. Being a teen, he'll cum quickly and recover even quicker."

Olivia followed my instructions and began stroking his cut cock slowly and carefully as he continued to play with her breasts and nipples.

"I suggest you stroke a little harder and that you wet your hand so it mixes with his precum and provides lubrication."

She did this, wetting her hand then continuing to stroke him faster.

"Just so you know what is possible and what guys like, just let go of his cock with your hand, then reposition yourself and open your mouth, then slide your mouth over his cock, trying not to scrape your teeth along it."

Olivia looked at me questioningly, but carried out the instruction nonetheless. Very quickly she developed a semblance of technique as she stimulated him orally, the effect being clear to see on his face.

"Now, while you're doing that, you can cup his balls in your hand and massage them gently. Remember that they're very sensitive but you can experiment gradually and you'll find the more he is stimulated the greater the pressure he can tolerate."

Olivia carried out my instructions and Rick ascended to a whole new level of sensation, lying back on the bed and focusing solely on his pleasure, my presence clearly forgotten. After a short time, he began panting and moaning.

"Olivia, if you keep his penis in your mouth, he will cum and squirt his cum in your mouth. That's fine if you want it and you can continue if you wish, but maybe that's something you can experiment with later on your own if you wish."

Olivia quickly removed her mouth from over Rick's cock and continued stroking it with one hand while continuing to play with his balls. In only a few seconds, Rick let out a moan, his hands gripped the bed sheets and cum spurted high into the air. Instinctively, it seemed, Olivia slowed her stroking as the fountain turned to an ooze, Rick relaxing, trying to regain his breath and composure.

"Well done both of you," I praised them, "I assume that's the first time you've done that together."

"Yes, we've both masturbated and of course we've seen it on porn sites, but I've never seen it in real life. It's much more exciting for real than on video."

She leant down and kissed Rick on the lips. He embraced her and held her to him, taking the kiss and the embrace to a higher level of eroticism. He reached behind her and unfastened her bra, then pulled it open and slid his hands over her breasts as she lifted her upper body to assist. They caressed and kissed for a long time, each arousing the other more. Rick's cock had earlier started to wilt but their amorous activities brought it back to full erection. Eventually, Rick made his move, rolling Olivia onto her back and propping himself up on his elbow.

"Well, you certainly don't need any instruction on kissing and arousing each other," I complimented them, "Now, Rick, have you ever masturbated Olivia?"

"No, she'd never let me inside her panties. Said it led too far down the track."

"So, first thing is to remove her panties. Just slide them down her legs and make sure they're off at least one foot, unless you want Olivia to keep her legs together."

Rick stripped Olivia so she now lay on the bed naked, as was Rick. Then he looked closely at her pussy, seeing for the first time what he had been feeling beneath panty fabric for the last little while.

"May I touch?" he asked Olivia.

"Of course, darling."

He parted her labia and looked inside. I stood and approached, indicating her outer and inner labia, her clitoris, her urethra and the entrance to her vagina. He touched and gently stroked her pussy, watching as her juices provided increasing lubrication.

"You can insert you finger a little way into her vagina, but don't push hard if you want to take her vagina with your penis."

He did, pushing up to his first knuckle, then just gently stroking in and out. I then told him to begin stroking her clit, which he did, causing Olivia to moan and move her hips gently.

"Just keep doing that for a while," I told him, watching her body as he became aware of the ability he had to stimulate and provide incredible sensations to his girlfriend. As he continued the massage, Olivia's moans became louder and her movements became more rapid and demanding.

"Just stop for a few seconds, if you can," I suggested.

Rick stopped, despite Olivia's apparent enthusiasm to continue.

"I was soooo close," complained Olivia.

"I'll continue in just a moment," reassured Rick.

"Now, if you want to, you can also use your mouth on her pussy," I told him.

He looked at me doubtfully, so I continued. "Just open your mouth and place your lips over her labia, then you can use your tongue to lick her labia, maybe enter her entrance a short distance, but most especially, to lick her clit. See if you can give her an orgasm that way."

He placed his mouth over her labia and obviously, from Olivia's response, he did something right. Olivia gripped his head in her hands and moved him slightly as her head tilted back and a smile flickered over her intense countenance, alternating with concentration. It took less than a minute before she was cumming, moaning and rolling her head from side to side as her orgasm swept through her.

As she began to come down from her peak, I tapped Rick on the shoulder.

"Just taper off the stimulation now," I told him quietly.

He did, and after a few seconds he raised his head and looked at his beloved, smiling as he watched her recover from the first orgasm he'd given her. He moved forward and the lovers kissed for a long time.

"Thank you. darling," said Olivia when they broke their clinch, "I taste pretty good, eh".

"That's Ok, sweetheart, pleased you enjoyed it. Yes, you taste great; I can see we'll be doing that lots more."

I noticed that Rick's cock was hard as steel, so, now that Olivia had recovered and was nicely relaxed, this was the perfect time for her deflowering.

"Rick, the time has come for you to pluck Olivia's cherry," I told him, "First you need to wear protection. Do you have a condom?"

Rick looked up at me aghast. "No, I haven't. Do I need one?"

"Yes, absolutely, unless Olivia's on some form of birth control, which I'm guessing she isn't."

Olivia was shaking her head, confirming my supposition. I reached into my pocket and removed a condom, opening the packet.

"Here, I'll show you how to fit it."

I expertly squeezed the end, placed it over his cock and rolled the rubber down his shaft. "That's how it's fitted. I'll teach Olivia as well so she can fit them in future if you wish. It can increase arousal for you both if you incorporate that into your foreplay. Now, just move your body so you lie face down between her legs with your hips a little below hers, then take your weight on elbows and knees. If you want you can use your mouth or hands on her tits. The important part is to position your penis at her entrance."

Rick positioned himself and kissed and licked her tits before covering them with his hands, automatically, it seemed, squeezing her nipples gently between fingers and thumbs. Olivia moaned from arousal.

"Now, Rick, you need to do the most important thing; ask Olivia for her consent to enter her and take her virginity. It's really important that you obtain consent before doing this every time. Just because she's your girl, just because you may even be married to her, does not give you the automatic right to enter her sexually without her permission."

"Honey, may I take your virginity right now?" asked Rick.

"Oh yes, darling, yes, yes, yes. Put your cock into me, fuck me, make me a woman, but do it now, for god's sake; I'm hot and ready for you."

"So, slide your body forward, lift your ass into the air a little, then slowly and steadily thrust your hips forward, moving your penis into her entrance. When you feel the barrier, just stop and hold still."

I watched him do that, moving about an inch in, then he held still.

"Now, this may be painful, Olivia. Rick is going to push forward hard and hopefully break through your hymen then slide further inside you. Are you ready?"

"Oh yes, very ready; do it."

"Ok, Rick, push hard into Olivia's vagina."

Rick thrust forward as Olivia bit her lower lip in pain as his cock head sought to tear through her fragile membrane. At first nothing seemed to happen and I became a little concerned in case this was a particularly tough hymen, but then she let out a short scream and Rick's hips rushed forward as he broke through the barricade and filled his loved one's vagina. Once inside, he remained still, allowing himself to become accustomed to the sensation and allowing Olivia to recover from the pain. After a few minutes, during which time they were kissing and caressing each other for the first time while she was impaled on his rigid member, I told them to begin the instinctive movements which would bring them both so much pleasure. He began fucking into her, back and forth, as she lifted her hips to him, seeking more sensation, more pleasure. They kept up a consistent pace for about five minutes, then Olivia began pulling and pushing with her hands on his ass to increase the rate, at the same time moaning softly as she climbed the slope towards her release. Rick sensed she was nearly there and increased both the strength and the rate of his movements. The changes each partner made fed back to the other, increasing the sensations for both until both were panting hard from exertion. Then Rick thrust deeply and tensed as he squirted his cum into his condom.

After he'd finished cumming, he relaxed on top of Olivia for a few seconds, then took his weight on elbows and knees to allow her to regain her breath.

"Did you cum, honey?" he asked her.

"No, darling, but I got real close."

"Oh. Sorry, my darling, you probably really need to cum, and now my cock's drooping so he's not much use for a while."

"Why don't you just cuddle again for a bit? That way you'll find that your young, virile penis will recover very quickly and be ready for action again soon," I suggested, "Besides, you need to remove the condom and fit another one. Once it's filled, it's far more likely to break if you continue."

Rick withdrew his cock, holding the base of the condom as I instructed; I noticed traces of blood on the condom and around Olivia's entrance. I handed her a towel and she wiped herself while Rick removed his condom, wiped his cock on the towel and fitted a new one by himself. They then cuddled together, each caressing the other, Olivia paying attention to lovingly and gently stroking Rick's cock, noticing how her actions caused it to harden. After 15 minutes of this attention, he was ready to go.

"Right, Rick, lie on your back and Olivia, you straddle him with your thighs so that his penis is below your entrance."

They moved into this position, Rick's hands automatically moving to her breasts.

"Now, Olivia, reach between your legs and position his penis so it slides into your vagina as you sit down."

Olivia did this and was soon sitting astride her lover, impaled on his rampant spike. They needed no more instruction from me. Olivia leant forwards and found the pleasure of her clit pressing against his cock and pubic bone. She ground her pussy against him, visibly becoming more aroused. It only took a few minutes of this before she lost control, arched her back and screamed her orgasm to the world. I expected her parents to come running, but they did not, fortunately. Rick held her hips, moving her back and forth gently to keep up the arousal for them both. Slowly she became aware of what was happening and began fully participating once again, repeating the movements that had given her such pleasure a few moments ago.

Very soon Rick was obviously close to cumming, thrusting his hips upwards against his lover's pussy, as though seeking to plunge even deeper inside her. She was moving rapidly, thrusting her hips forward and back, leaning forward and enjoying the sensations of her clit being stimulated on her lover. Then he thrust upwards and held still as he filled another condom, causing Olivia to cum in the process. She avoided the scream, but arched backwards, then collapsed forwards, panting as she lay on Rick's heaving chest.

After a few minutes, during which time both partners hugged and kissed each other, Olivia sat up and Rick held the condom while she moved off him and sat on the side of the bed. She looked radiant, with that freshly fucked blush to her cheeks that is usually so distinctive. She reached out her arm and helped Rick to sit up, then he swung his legs around and sat beside her, his arm around her waist.

"Thanks so very much, Hank. We've learned lots and I'm certain that losing my virginity would have been far more difficult and more painful without your help."

"That's Ok," I replied, "I was pleased to be able to assist. Your parents have my contact details so if you have any questions please just call me. I'll head downstairs now and leave you two love birds to come down when you're ready. Just remember the two 'c's - consent and condoms, although as you'll probably be doing this daily from now on, it may be advisable to use some more effective and less intrusive form of contraception."

I stood up to walk to the door, but Olivia stopped me, gazing at my bulging crotch.

"It doesn't really seem fair, does it, we have all the fun and you go away obviously aroused as hell. Would you let me help you now?"

"What did you have in mind?"

"Well, one thing you haven't taught me is how to swallow cum, so I think I need to learn that before you leave."

"Only if you're certain you want to do this," I replied, suddenly excited by the offer to allow me to squirt my cum into her virgin mouth, "But I'd be very grateful. As you observed, I'm really horny."

Olivia didn't reply but instead knelt on the floor at my feet and unfastened my zipper, belt and trouser hook. My trousers went south and she wasted no time in stroking my hard cock through the thin fabric of my undershorts. It felt heavenly; arousing, stimulating and very sexy. She gazed into my eyes, then slipped her thumbs inside the elastic on both sides and pushed the undershorts to the floor. My cock popped out, waving just in front of her face. She held it gently in her hands, measuring it with her small hands, comparing it with Rick's, who was considerably smaller, then let go with one hand and cupped my balls, squeezing them gently as she moved them in their sac.