Chapter 14

Two football games had already been played, and Cheryl was very concerned. Greg had gained right around 100 yards in each game, although he had fumbled once. She talked with Cal on Monday night, trying to arrange a time when they could get together. She was adamant that it had to be before that Friday's game.

Finding a time and place was actually rather tough. The rendezvous had to be kept secret from both sets of parents and from Greg. That ruled out Cheryl's home, and it made evenings problematic, since Greg tried to keep track of everything she did. They could have used Cal's home during the day because both parents worked.

Cal asked Cheryl if he could call her back, then made a quick call to Teri. When he called Cheryl back, they decided that using Teri's spare room during the day was the best option. It then became a matter of deciding when they could both skip classes.

Wednesday morning, Cheryl had lunch and study hall back to back. Cal would miss one class, but he was not as concerned as she was about grades. The bad part was the unromantic circumstances they found themselves in. She had managed to get a car, and drove them to the Walts'.

Cal almost broke into tears when they reached Teri's guest room. Cheryl did. The room and its en suite bathroom had been transformed into a love nest. The curtains were closed and there were more than a dozen candles scattered about, with a lighter on the bathroom counter. Soft rock music was already playing when they arrived. An ice bucket contained champagne and cola, and there was a saran-covered tray of fruits, cheeses, and small sandwiches. The covers were rolled back on the bed, and two matching robes were nicely folded at the foot. On top of one robe was a note 'Use the Jacuzzi'. On a night stand were three condom packets and a tube of KY.

As strained as their arrival had seemed, Teri's loving efforts went a long way toward building a mood conducive to making love. Cal had never had much alcohol, but he went right to the champagne and poured a glass for each of them. Cheryl was a bit hesitant, but she accepted it and sipped it slowly.

Cal had a personal dilemma. As far as Cheryl knew, it was his first time, but to make it good for her, he would have to take charge. That would reveal his experience. The decision had to be made right then, and he decided in favor of her satisfaction.

Taking her hand and having her sit beside him on the bed, he told her "I need a promise from you. You're going to find out something that I need to have kept secret. Will you do that for me?"

As nervous as she was, Cheryl managed a little chuckle. "With what I have to keep secret here, how could I think of telling your secret. Of course I promise."

"That's what I thought, but I had to make sure. It really is important. Cheryl, I have done this before, a number of times. I'm not going to tell you who I was with, just that it was only one person, and that she is completely safe."

"I think this will work best if I take charge," he went on as he began unbuttoning her blouse. "Ever since the night of the pictures, I have been dying to see all of you again." He interrupted his work on her blouse with a gentle kiss.

The night of the memorable picture, Cheryl had seemed supremely confident displaying her beautiful body. Perhaps it was the staged setting. Perhaps it was Teri's presence and assistance. Whatever had happened then, she was now too nervous to speak, and her hands shook as she removed her blouse after he had unbuttoned it.

Cal was about to ask her once again if she really wanted to go through with it, but he realized that what she needed was relaxation and comfort, not more well-meaning doubts sowed by him. On the bathroom counter, Teri had left a large towel with some body oil on top of it. A massage would be the perfect way to start.

She had worn a skirt to school that day, something so unusual that Greg might have been suspicious if he had paid any attention. Kicking off her sandals, she removed the skirt to stand in her very nice bra and panties. She was a little confused when Cal walked to the bathroom, but seemed to understand when he came back with the towel and the oil.

Blushing brightly and shaking a bit, she turned sideways and took off her bra. With her shoulders hunched forward and her near arm hiding her breasts, she looked over at him with her lip quivering slightly. When he smiled, she dropped her hands to the tops of her panties. She was still sideways to him, but she presented a lovely profile. Her hands were frozen, seemingly unable to finish stripping.

"Just leave them on for a while," he reassured her as he helped her lie down on the towel. Before opening the oil, Cal caressed her back reverently. So many times since the picture he had enjoyed visions of her lovely back. Now, he reveled in the tight smoothness of the luxuriously cushioned muscles. He traced the straight, proud line of her shoulders and the sensuous taper down to her taut waist. The frilly, skimpy panties adorned rather than covered the enticing mounds of her ass. His hands were drawn almost irresistibly to her bottom, but he somehow pulled back, respecting her nervousness.

Time was a problem, but Cal was determined to make the experience as good as he knew how. He could have spent hours just doing her back, but he had to move things along. He moved down to her feet, and as he worked up over her calves, he could feel her start to relax. By the time he reached her thighs, she was making small sounds of contentment.

Not saying anything about it, he took hold of her panties and began sliding them down. To his relief, she raised up to assist him. When he first rubbed oil into her cheeks, she flinched, but his efforts soon brought back the contented sounds.

At that point with Teri, he would have had her roll over, and the sexual intensity would have increased quickly. With Cheryl, he felt the need to move her along a little more slowly. Standing by the bed, he took off his own clothes as she watched. He could feel her gaze on every bit of skin that was revealed as he took off his shirt. When he dropped his jeans, her eyes locked on his bulging crotch and stayed there as he finished stripping. Her breath caught when his erect cock was finally bared before her. She probably expected him to lie down with her, but instead, he held out his hand. "Let's take a shower and get the oil off, OK?"

When she stood, still nervous about frontal exposure, he pulled her to himself for a kiss and she responded with feeling. Still worried about rushing her, he led her to the attached bathroom for the guest room. He thought about Teri's offer of the Jacuzzi, but time was too short. Besides that, he thought it would make her more nervous walking through someone else's house.

Teri had made it clear on several occasions how important it was not to get the woman's hair wet unless she said it was OK. Cheryl wore hers short in deference to her sports, but he was still careful of it. He began with her back and washed all of the areas that he had oiled. She seemed able to relax through that, but flinched when he turned her to face him and started on her shoulders and chest.

Dropping the rag he had been using, he gently soaped her breasts and tummy with his hands. He did not try to avoid the rigid nipples, but did not give them any special attention right then. He worked from her feet upward, feeling her tense up as he approached her crotch. Again, he was a little surprised at her timidity.

He was certain that Cheryl would have bathed in preparation for the big event, so cleanliness was not his concern. What was important was the first touching of her pussy, and the shower was a good place to breach that psychological barrier. He tried to keep it business-like, not spending any more time on her cleft than it took to make sure she was clean. It still made her hiss and shudder. He decided not to worry about her anus, but she took over for him with a small blush.

The next part was important for her impending liaison with Greg. When she was all washed and rinsed, she knew it was her turn to wash him. She went at it with enthusiasm until she got to his stiff cock. There, she slowed down and handled it tentatively. He did not want to ask, but it appeared that she had managed to go out with Greg all of those months without even giving him a handjob. She really did have some kind of hold on the big guy.

"You need to make me come, Cheryl. Young guys don't have much control. If I come now I will last longer when I'm in you." She looked at him with a little surprise, but was soon stroking and fondling him. It was thrilling to feel her touch, but it was much too gentle to get the desired result. When he made suggestions, she took it in the right spirit, apparently not embarrassed about her inexperience.

Cal kept thinking about Teri and how wonderfully she had guided him through all of his firsts. He was determined to pass on the benefit to Cheryl, and it was definitely not a chore. Just from watching her at volleyball practice all of those times he had fallen into lust for her. The picture session had only increased those feelings.

After hearing about her incredible deal with Greg's grandmother, he was more than a little in love with her. He hated that she had to give herself to Greg to achieve her goal. But he could relate to the level of commitment that made her do it. For him, it was protecting those he loved; for her it was an M.D. For both, it took effort and sacrifice beyond what most people would give. He loved her for that.

Her technique may have needed improvement, but it made little difference to Cal, simply because of the feeling she put into her ministrations. Between her hands and the thoughts running through his head, it was not long at all before she was rinsing the semen from her tummy while he tried to recover his breath.

Cal had heard that athletic girls often broke their hymens somewhere along the line, but she had asked him to 'take my cherry'. After drying and getting into the bed, he asked her as he pulled her in for a kiss. "Do you still have your hymen, Cheryl?"

Dropping her head to his chest, she told him "Yes. My doctor said mine is pretty strong and it would probably be painful when it broke. She offered to cut it, but I... I don't know. It's the symbol, I guess. That's one reason I wanted you to do it, not Greg. If you have to hurt me, I know it will hurt you to do it. That means a lot to me."

That was another time when Cal was brought close to tears. He felt that he had met his match in strength and determination. He would do everything he could to make it as easy as it could be. Glancing at the nightstand, he saw the condoms, and it forced an unpleasant discussion.

"Cheryl, I'm hard again. It's a good time for you to put the rubber on me."

"Oh, I don't want to use one. It's my first time and I'm on the pill. I trust you to be clean."

"I don't want to use one, either. But you must never, ever, let Greg into you without one. You already know that he fucks around. Even if it is only half as much as he brags about, it is still a danger. Part of getting ready for him is learning to use them right."

It was probably not the best time for that particular discussion. He had managed to get her relaxed and enjoying herself, but the subject of condoms brought the enormity of her bargain crashing down on her. She lost it. All he could do was hug her, and in the process, their bodies were pressed together in the most intimate contact, yet. As he comforted her, she seemed to want to burrow right into him.

It took several minutes, but her emotions of regret and fear started to change into arousal as he kept up gentle stroking and encouraging words. He would not have set it up that way, but it was working out. As soon as he thought she was ready, he started a long, intense kiss.

From the kiss, it was a progression that Teri had helped him to perfect. Deciding that the condom issue could be deferred at least for their first coupling, he began the wondrous journey down her body with his mouth and his hands. With Teri as his only previous experience, the newness of a different body and different responses made it a priceless privilege.

Perhaps out of some dissatisfaction over their modest size, she seemed to shrink back a bit when he began kissing her breasts. It only took a little attention to her bloated nipples, though, before any concern other than wanting more was wiped from her consciousness. Teri had once mentioned that young girls who had never nursed a child had nipples even more sensitive than her own. Cal quickly verified Teri's comment as sucking and light nibbling almost brought Cheryl up off of the bed. He had to find the right pressure that triggered her arousal without causing her to shrink back from the sensitivity.

When he moved his kisses down over her near-six-pack tummy, Cal kept one hand playing with a nipple. After many licks and kisses and a playful tongue into her 'innie', he dropped his hands to her thighs and pushed her legs apart.

Cheryl had thought she knew what she would be giving up - what she would be experiencing. She had willed herself not to be embarrassed when she exposed her body, and she had steeled herself for the pain that she knew would come from the first penetration. But she had not anticipated Cal's mouth on her most private spot. Of course she had heard about oral sex, but had not prepared herself mentally as she had for the exposure and the pain.

Because of her general nervousness, Cal was not surprised when she resisted his first attempt at spreading her legs. It did not take her long to relax, and he decided he needed to give her a reason to open up. Stroking gently along her hips, he stuck his tongue as far as it would go into her pubic hair between her squeezed thighs. Licking forward and up, he was able to bring enough sensation to responsive tissues to let her know that it was something she wanted more of.

Nervous she may have been, uncertain, even. But Cheryl was also decisive. Just the delightful tingling as his tongue touched the top of her cleft was enough. Opening her legs wide, she reached down and took his head between her hands, guiding him downward.

Having only Teri as a reference, Cal set out to take Cheryl through several cycles of arousal almost to release. The only problem was, he misjudged. She probably was no more responsive than Teri, but the combined anticipation and fear had put her on a very short fuse, and she surprised him by coming while he thought he was still just warming her up.

Again, relating to what he had learned from Teri, he backed off to avoid her over-sensitized clit. That did not suit her, though, and having lost any timidity, she let him know by pulling his head into her crotch and gasping out "More!" That gave him the chance to do what he had planned and many minutes later, he sent her into the hoped-for monster climax.

As he feasted between her legs, Cal had decided to let her get on top for the first penetration so she could have control of the pain. After her huge orgasm, she was limp but still twitching and extremely well-lubricated and he changed his mind. Sliding up over her quickly, he managed to open her slightly with one hand and get his head between her labia.

From there, he made a series of very short thrusts to get far enough in so there was no danger of being squeezed out. With no experience to go on, he did not know if it was better to break her barrier with one brutal thrust or to ease through it in smaller intrusions.

Cheryl resolved that debate for him. She had recovered more than he realized. Bracing her feet, she raised her bottom a little, grabbed his ass with both hands, and pulled. The first try almost popped him out. He was not at the perfect angle and the bending of his rigid shaft hurt. Consoling himself that the pain was much less than she was about to go through, he corrected his angle, and did the next thrust himself.

It must have hurt because she squeaked and jerked, but she did not back off. It was clear that he had not gotten completely through and he hated the thought of having to hurt her again. She, however, had a one-track mind. She wanted to get it over with, and once again she pulled him strongly toward herself.

That time was enough to get through. A load groan escaped her and he looked up to see moisture in her eyes as she relaxed her legs and breathed deeply. For Cal, it was a very helpless and disturbing feeling. He had heard guys in the locker room bragging about the thrill of breaking in a virgin, but he felt no thrill at all. If anything, he felt guilty for having hurt her and frustrated at not knowing how to fix it.

The one thing he could do was to be tender, so carefully holding still within her, he kissed her teary eyes, then her mouth. After breathing deeply for a minute or so, she looked at him with a strained smile. "Damn. I'll never let my patients talk me out of cutting the stupid thing."

"Do you want me to pull out?"

"No way! From what I heard, the pain isn't supposed to last too long. Can you hold yourself there? Can you stay hard?"

"Staying hard could never be a problem when I'm naked with you." That had just popped out, but it was just what she needed to hear. Tentatively, she pushed her pelvis toward him just a little, and he felt his cock sink a bit deeper. It must have still hurt, because she was motionless again for quite a while before the next little push.

It must have taken ten minutes, and Cal's arms were feeling a little shaky by the time his pubic bone bumped her clit and she hissed at the contact. Teri had taught him how to stimulate her with little circular motions and he started doing that to Cheryl. Her clit was quite a bit larger than Teri's, and it must have felt the contact a lot more. It was not long before she was showing signs of arousal rather than pain.

At that point, Cal made a tough decision. "Cheryl, I would love to keep doing this until I come, but you're not ready for Greg, yet. I'm going to pull out so you can practice with a condom."

"Can't you get hard again if you come?" she begged.

"Maybe, but I want to make sure you are ready for him. Besides, you must be pretty sore inside."

"Yeah, I can feel some pain. But there are some really good feelings, too."

"Well, once you get the rubber on, we can try again if it doesn't hurt you too much."

With typical thoughtfulness, Teri had several small towels, a washcloth, and a bowl on the bathroom counter. Reluctantly pulling out of her tight, hot sheath, Cal went into the bathroom, washed himself, then brought back a warm, wet washcloth for Cheryl. There had been a little blood on his cock, but fortunately, there was none on the sheets as he gently wiped her crotch.

With the condoms, it was a case of the blind leading the blind, and they were reduced to reading the instructions on the packet. It was a good thing there were three because it took all of them to get one on correctly. The process involved a lot of giggling, and he even lost some of his rigidity. When he was finally encased properly, she asked if he wanted to try again.

"Are you willing to miss another class?" he asked her.

"Shit!" she spat out as she looked at the clock, "Greg's in that one with me. I don't want to have to make up a story." It was not the kind of resolution either of them had hoped for. Cal wondered if he should have spent less time with the massage, the shower, and going down on her. After thinking about it, he decided he had given her the loving things that Greg would not or could not give. The fucking Greg would do. He had done his best for his friend in the time they had.

Greg came up fifteen yards short in the game Friday night. There was a rather angry, half-hour long argument between him and Cheryl afterward about that being close enough for her to pay off. She stuck to her guns.

It was wonderfully empowering when she really did not care if he dumped her. Of course, there was a great deal more money that could be made. On the other hand, if Greg dumped her, she might be able to go out with Cal. At times, that prospect seemed more valuable than the money.

The hold she had on Greg still puzzled and amazed her, but she had come to accept it and to use it. Already, she had been able to steer him away from two situations that could have caused him real trouble with either the coach or the law.

Cal was not totally surprised to get a call Sunday morning. "After a big argument, I'm staying home while the rest of the family goes to church and to Grandma's for dinner. Can you get over here? I'm without a car."

It took Cal about twenty minutes on his bike, but the vision that opened the front door to him was well worth it. Cheryl wore a short, silky robe and it was quite obvious that there was nothing underneath it. Her welcoming kiss was toe-curling, but he detected a little tension in her.