Brenda and Bobby Ch. 1

"That feels good, will you give me a massage when we're done with you." I asked.

"I'll try if you want." he said, still fondling my large breast.

He was doing so well I had to go for it. I put more oil in my left hand and reached for his cock. I slowly began to stroke it. "Let me know if you want me to stop." I said, "but I think you are ready for this."

I gave him a Very light teasing stroke, my long fingers covering the entire length of his very hard cock. I gently rubbed his sack, feeling his warm balls getting tight in their pouch. I could feel myself getting wet, but I remained focused on his breathing, making sure he could handle the stimulation.

Milk was leaking down his arm as he continued to fondle me, but this was no time to stop for cleanup. I could see the head of his cock getting deep red as I continued playing with him. If he could hang in a little longer I'd be able to make him cum.

"You're doing fine. Keep breathing deep. I'm going to make you cum. Don't fight it just let it out." I said.

The words had no sooner left my lips when a thick white stream shot out of his cock onto his belly and chest. His body tensed as it spurted again.

He let out a sigh as I stopped stroking him. He looked into my eyes with a dreamy smile, not knowing what to say. I reached for the towel and wiped the ejaculate off his body.

"Was that OK?" I teased, "Are you all right?"

"Wow!" he said, "So that's what it feels like."

I let him rest for a minute, watching his chest rise and fall with his breathing. I couldn't suppress a huge grin on my face. I had forgotten how grateful some of my erotic massage customers were when I had successfully relieved them of their semen. Men really do need that release.

In a few minutes he began to become alert. "Ready to do me?" I reminded him.

"Oh sure..." he stammered. I traded places with him, lying naked on my stomach.

He began to rub oil into my back, trying to recreate what I had been doing to him. He wasn't half-bad. After about 20 minutes I rolled over onto my back. "That's good." now do my front." I encouraged.

He was awkward at first, not sure of where he should touch me or where he shouldn't. Gradually he began to figure out that there were no locations that were off limits. He gently kneaded my breasts, causing more milk leakage.

"Don't worry about a little spilt milk." I teased, "I won't run out." He continued his small hands working on my big breasts. My pussy was getting very wet. He gently pulled on my nipples. I couldn't stand any more.

I took his right hand and brought it down to my pussy. I took his index finger and positioned it on my clit. "Rub here, start softly and increase the pressure as I get more excited." I commanded.

His eyes were big as he began masturbating me. It felt so good. "You can do some exploring if you like." I smiled, "This is supposed to be a learning experience."

He slipped a finger into my vagina and probed around a bit. I'd soon teach him how to stroke my g-spot, but not today. Today I'd be happy with a nice clit-based orgasm. He continued stroking my clit and my lips, sometimes darting into the vagina. I was getting really restless. I'd be cumming soon.

"When I cum stop rubbing there for a few minutes. Then start over and do it again." I implored.

"How will I know when you cum?" he asked innocently.

"Don't worry, I'll tell you", I gasped, "I'm getting close."

He took that as a sign to increase the pressure and tempo, and I was soon bouncing up and down on the table until I exploded with pleasure. In my excitement I forgot to tell him I was cumming, but I guess he figured it out. As I was recovering my breath he stood over my head and played with my nipples, getting them incredibly hard. In a few minutes he was back to my clit revving it up for round two. My second orgasm was even more powerful. I almost fell off the narrow table.

Bobby went back to playing with my nipples while waiting for me to recover. A third round would be overkill for today, I thought as I caught my breath. "That's good!" I panted. "That's enough for now."

I sat up on the table and noticed that Bobby was again fully erect. He evidently enjoyed playing with me as much as I enjoyed playing with him. I hopped off the table, my full breasts bouncing to and fro.

"Why don't you lie on your back again. I think you've got more ejaculate that needs to come out." I said helpfully.

Bobby was much more relaxed this time as he lay on the table. He was doing so well I decided to go right to his cock. I put plenty of oil in my hand and began stroking with long moderate tempo motions.

"You're doing great so far!" I said, watching the head of his cock get darker as I worked the oil into it. His breathing was still regular. I was confident I'd soon get him off again without incident. His hand went to my breast without any urging on my part. Drops of milk once again were expressed as he fondled me.

"That feels so good', I cooed, "Would you do me a favor?"

"What?" he asked as I stopped stroking his cock for a moment?

"I'm so full of milk, would you mind taking some?" I implored. I wanted to ratchet up his arousal to another level.

"OK...sure." he said.

I leaned over and offered my right breast to his lips. He gently began sucking the warm milk fresh from my bulging breast. I leaned over even further until my breast was fully resting on his face. I made sure he could breathe as I encouraged him to suckle.

"That's so good! Oh yes..." I said.

I let him suckle for about 5 minutes before I returned to focusing my attention on his cock.

"' I'd really like you to cum again if you don't mind. ", I said, resuming my stroking of his cock while he continued hungrily devouring my breast. The head of his cock was deep purple; looking like it was ready to explode any second. "Let it cum, Bobby, I want your load."

His breathing was still moderate. So I pumped him even faster. His back arched and his muscles tightened.

""Let it cum!" I implored. I wanted him to get off while sucking on my breast. I could see the tip of his cock open up and then his milky load shot out all over his chest and my breast. I could feel his ejaculate beginning to dribble down my left breast as he resumed sucking my right one.

"I think you are done for now!" I laughed, as I toweled off his chest and my left breast. "You did great. I know you'll have much better luck with your next girlfriend. By the time you get to Stanford this fall you'll be ready for anything a coed could want."

"Thanks, Brenda. I don't know how I'll ever be able to repay you for your help." Bobby said.

'You'll repay me by getting healthy and enjoying a full life." I said, and I meant it.

Another week later...

Bobby's health continued to improve. I gave him a thermos of milk to bring to school every day, so he was getting three meals a day. After school I'd give him fresh milk while working him on the massage table. Still no asthma attacks. To my knowledge this was the longest he'd ever gone without an attack. He was up to 3 miles per hour on the treadmill. It was amazing. The only problem was that I was running low on stored milk, and the pump was starting to irritate my breasts. I decided that when school was out I'd convert him to three meals of fresh milk instead of one.

Another Saturday breakfast, this time pancakes for a change. Regular for me. Pancakes made from my milk for him. I didn't bother to tell him about the unique pancakes, wanting to see if he would notice.

"These are really good, Brenda!" he said. "I'll have plenty of energy today."

"They are pretty good." I said, deciding to keep their origin to myself.

"Feel like learning some new skills today?" I added casually, "you're doing so well."

He blushed. "You're in charge." he said, smiling. "So far everything you've suggested has worked out."

"Now that you can cum without triggering an asthma attack, I'd like you to learn how to control when you are going to cum.", I said. "It is a skill you need to be a good lover for those Stanford coeds."

"What do I need to do?" he said, cautiously.

"Well, have you noticed that just before you ejaculate there is a point in time when you know you are going to cum no matter what, but you haven't let it out yet."

He thought for a few seconds. "Yeah, I think I know what you mean. It usually is just a few seconds before it shoots out." He replied.

Bobby was even getting comfortable talking about sex. Real progress. " Well I want to practice having you recognize when you are close to having that feeling. I want you to tell me to stop before you get to the point of no return. Then we'll practice some tricks you can use to avoid cumming until you want to."

"Why wouldn't I want to?" he asked, puzzled.

"Because you might have a girlfriend who takes longer to cum than you do." I said, "A good lover will get his girlfriend off before he let's himself cum. At least most of the time. Besides, a guy who can cum on command is very impressive to most women. I can teach you how."

"When do you want to teach me?" he said, already surmising the answer. "Let's get started." I said.

He was doing so well that while I still watched his breathing closely, I wasn't too concerned about triggering an attack. He was developing confidence in himself as well, making an attack even less likely. I skipped the massage and went right to his cock. He had a lot to learn, so there was no sense in wasting time. After playing with him for about 10 minutes. He was pretty far along. His cock was rock hard and the head was beet red.

"Now don't wait until it is too late." I said, "Let me know when you are getting close." I continued stroking him pretty vigorously. I withheld my breast so he wouldn't get too distracted.

"Stop!" he blurted.

I immediately squeezed the head of his cock with my fingers. This reduced the sexual tension right away without hurting him. We continued this process again and again for the next half-hour. The intervals were getting shorter as he was getting more and more aroused.

"Brenda, I'd really like to cum.", he implored. This was what I was waiting for. He was now at his maximal state of arousal and his breathing was still good.

"Not quite yet, but soon". I said, "I'll tell you when it is OK. I want you to think of something really disgusting now, really revolting. You don't have to tell me what it is, just do it."

He lay quietly for a moment. "OK." I've thought of something.

"Now focus on that thought while I continue masturbating you." I added. I played with him more slowly now, given that this was just a training exercise. I wanted him to be successful. He stopped me a half dozen more times. He was doing great.

'Please, Brenda, I don't think I can hold it anymore." He said. "Yes you can. I responded. "I'll show you how. When you feel you are getting close bite your cheek with your teeth. Don't draw blood, but bite it hard enough so it hurts."

Amazingly for such an inexperienced guy, he was able to do it He stopped me another half dozen times. I couldn't believe his control for this first exercise. I looked at the clock. He'd been on the edge for an hour. If a coed couldn't come in an hour, she never would, I thought to myself.

"OK, you did fantastic!" I exclaimed, 'Let yourself cum right away. You've more than earned it." I popped my milky breast into his mouth and pumped his cock with my pre cum covered hand. His cock was totally juicy for the first time. This would be an orgasm he'd remember.

His whole body shook as he shot a giant load all over himself and all over me. It was glorious. I milked every drop I could before toweling us off. He was breathing hard but not wheezing. He'd passed another milestone. He deserved a reward.

"Are you OK?" I asked. "I know that wasn't easy but you did great."

"I'm OK" he panted. "It felt like a nuclear blast between my legs." he smiled.

"The only problem is that delaying your orgasm for such a long time creates more tension that it releases, so I want you to cum again as quickly as you can." I urged.

Even with the powerful orgasm he was still rock hard, as I knew he would be. I took his cock in my mouth. He'd earned is first blowjob.

"Now cum as quickly as you want, but tell me when you are going to lose it. It isn't polite to cum in some ones mouth without giving them warning. Now I get to drink your milk!" I teased. As a masseuse I never gave blowjobs, even though a lot of guys wanted them. A hand job was just a technical exercise, but sucking someone's cock was real sex in my book.

It had been a long time since I last did this, but in a couple of minutes I was still able to go all the way down on him. Even though he was a short guy for his age, his cock was pretty substantial. Not huge, certainly, but more than adequate. In another few minutes he was ready.

"I'm going to cum!" he exclaimed. I gave a convincing moan, wanting him to think that having him cum in my mouth was my greatest wish. I was greeted with only a slightly smaller load than the previous one. I swallowed every drop. This time he started to go limp.

"Feel better?" I teased. All he could do was giggle. He was temporarily spent, but my pussy was throbbing with excitement.

"Follow me." I said, pulling him up from the massage table. I took the white towel and led him into my bedroom. I pulled down the bedspread and laid the towel out over the sheet. I lay on my back, with the towel under my butt so my dripping pussy wouldn't soil the bed. I spread my legs wide. Bobby's eyes got big as he took in what was a pretty nice view for an 18-year-old.

"Kneel between my legs." I commanded. He complied. "Now put your index or middle finger of your left hand inside my vagina and press on the upper surface. I'll guide you." I said. I took his hand in mine and we played around until his finger was just where I wanted it. "That's my g-spot. If you get me excited enough it becomes sensitive. You can alternate between playing with my clit and pressing on the g-spot. With practice you can keep a woman in an orgasmic state for as long as you want."

I told him to stimulate my clit until he could feel strong push out contractions in my vagina. He should then press on my g-spot and massage it until the contractions subside. He should then go back to my clit and repeat the process keeping his left hand in my vagina the whole time. He should repeat the entire cycle until he gets bored or I beg him to finish me. He should finish me by continuing to stroke my clit into an explosive orgasm that will almost shoot his left hand out of my vagina from the strong contractions.

Having been suitable briefed, we began. I was already so excited from blowing him that it didn't take long to get the strong contractions going. "That's it! Stop on the clit, stroke the g", I moaned. In a few minutes he was getting the timing pretty good. I was floating in an orgasmic cloud that I wanted to last forever. Unconsciously my hands went to my breasts and I began playing with them, gently pulling on the nipples. My eyes were closed and I could have been anywhere. I didn't care.

"Oh that's so good..." I moaned, "Don't stop." The minutes passed and my body quivered with pleasure as wave after wave of deep vaginal contractions swept over me. This went on and on until I couldn't stand it any more. Milk was seeping all over my chest but I didn't even notice and wouldn't have cared anyway.

"Finish me Bobby, finish me!" I pleaded, expecting instant obedience. Instead he ignored me. At first I thought he wasn't paying attention, so I pleaded some more. Still nothing.

"You can wait a little longer, Brenda," he said, "I'm having too much fun to stop."

My whole body was shaking. "I need to cum.", I pleaded, trying to shout it out but only managing a whisper. Finally he relented and kept stroking my clit until a wave of pleasure swept over me that was so intense that I accidentally squeezed my breasts so hard that to little streams of milk shot about six inches in the air. My whole body contracted in a seizure of pure pleasure that seemed to last for a minute but was probably only several seconds. Thankfully, he took his hands away and wiped them on the towel.

I was in such an erotic frenzy that I couldn't stand it. Watching my little fountains of milk had him rock hard again. I pulled him to me and his cock slipped in like it was custom fitted. Somehow I had enough presence of mind to tell him to breathe and not rush as he began to pump his cock all the way into me. The powerful contractions in my vagina returned with a vengeance. He was so short that his lips only came up to my nipples, so we couldn't kiss. He didn't seem to mind as he lustily sucked the milk from my breast while pumping me hard with his cock. My contractions were so powerful that they just milked him to a powerful orgasm, shaking his whole body. I could feel his warm load shoot into me.

We both giggled as we caught our breath. "I accidentally skipped ahead to next week's lesson", I panted.

"You're a good student."