Chapter 2

As I stood up, I reached down and helped Tanya to her feet. I put my arm around her and lead her into my bedroom. The sheer material of her see-through top felt sexy and wicked against my skin. I turned on the lamp on the bedside table and turned down the sheets on my king-size bed. I know ... you’re thinking ... what does a single guy need with a bed that big? At 6’-2”, I loved having the space; plus, I enjoyed the size of the big bed whenever I was “entertaining” guests. I pushed a bunch of pillows up against the headboard and lay down against them. I beckoned to Tanya to join me.

“Should I take my boots off?”

“Are you kidding me? No way. Leave everything on. You look so fucking hot in that whole outfit. I want to enjoy it.”

She eased herself onto the bed and as I put my arm out, she curled herself into the crook of my arm. As she settled in, those big voluminous tits of hers rested on the side of my chest. Man, they were nice and soft and warm as they pressed against me. I pulled her close and felt her bring one of her creamy young thighs up to rest on mine.

“So ... tell me about your evening with Martin.”

“Well, you were right, he was a virgin. But my God, that night ended up better than I ever could have dreamed of,” she said with a distinct note of pleasure in her voice. Her hand rested on my chest and she slowly traced teasing little patterns around with her blood-red fingernails.

“How old was he again?” I asked as I rubbed my hand around the smooth nylony material at her shoulder.

“He’s 16. I haven’t been with a boy that age since ... well ... since I was that age! I forgot about their enthusiasm and stamina. Young Martin turned out to be quite something alright. I think I’ve put him on the right track to be successful with women.”

“Okay, let’s hear the details.”

This is Tanya’s story...

When we left you brother’s place, I figured a good teasing wouldn’t hurt him so I made sure when I got into the car that my skirt rode well up on my legs. As he leaned over to put on his seat belt, I saw Martin’s gaze dart to the wide expanse of creamy thighs I was showing him. As I snapped in my own seat belt, I adjusted the shoulder strap so it noticeably pressed down between my tits as it crossed my body. I flicked my eyes up and saw Martin staring at them with his mouth open.

“You okay, Martin? You look all flushed,” I asked as we pulled away.

“Uh yes ... uh no ... I mean ... I’m okay,” he stammered as he finally tore his eyes away from my chest and looked out the window. On the way to my place, I talked to him about school, his job at the shoe store, pretty innocent stuff. I just wanted him to relax a little. Whenever he could, I noticed his eyes kept flicking back to my tits or my exposed thighs. I pretended to concentrate pretty intently on the road so he could look at me without having to be too concerned with me catching him. I looked down once and in the dim light inside the car, I could make out a sizeable bulge in the crotch of his khakis. At one point, I let my hand drop into my lap as I pretended to scratch an itch on the inside of my thigh. Out of the corner of my eye, I saw his eyes go as big as saucers as my dark red fingernails toyed along the smooth white skin just below the hem of my skirt. I figured I’d better stop or he might just blow that load right in his pants if I kept this teasing up much longer.

“Here we are,” I said as we pulled into the driveway of my Mom’s house. “Are you sure you don’t mind helping me? I’ve got a couple of boxes I need to move into the garage.” Actually, there were two small boxes of books that I had stuck up on my closet shelf after cleaning up my bookshelves. I had decided to donate them to charity. I hadn’t made them too heavy as I had been expecting to move them myself. I figured this was as good an excuse as any to get Martin into my room where I wanted him.

“No ... I ... I’m happy to help,” he said nervously as he got out of the car. I grabbed my bag and lead him into the house. I looked back over my shoulder at one point and his eyes quickly looked up from watching my ass. I smiled knowingly and watched him blush again. He followed me through the house as I turned on a few lights on the way to my room. With what I had planned, I was glad my mother was going to be away for the rest of the weekend visiting her sister. He stopped just inside the door to my room as I walked over and turned on the light on the bedside table.

“The boxes are just over here in the closet, Martin,” I said as he started to walk across the room as I pointed to the closet door. “Oh dear...” His eyes followed mine to my bed which was strewn with all kinds of lingerie. I had laid out a bunch of different things before deciding on what to bring over to visit you and Emma at your brother’s. He stopped dead in his tracks and I saw him gulp as we both looked at the array of corsets, nylons, panties and bras strewn across the bed. The kid had probably never seen this much sexy underwear in one place other than the Victoria’s Secret catalogue stuffed under his bed.

“Oh silly me,” I said with a little laugh. “I guess I should really learn to tidy up better. I’m sorry you had to see such a mess.”

“No ... no, that’s fine ... it’s not a mess at all ... I ... I bet that stuff looks real nice on you.” His voice was quivering and I noticed fine beads of sweat on his forehead.

“Well, thank you Martin,” I said as I stood before him with my hands on my hips and thrust my swelling chest out towards him. “You’re a real charmer. You know just what to say to a girl.”

“Th ... thank you, Tanya,” he said as he lowered his head shyly.

“So you really don’t have a girlfriend right now, Martin? I find that hard to believe.”

“No ... no I don’t,” he said softly, “I’ve always been pretty shy.”

“So, you’ve never ever had a girlfriend?”

He paused and then hung his head as he answered, “No ... I ... I never have.”

Perfect! He was a virgin ... this was going to be sweet! I reached over and softly put my hand under his chin and tilted his head up to look at me. “Martin, that’s nothing to be ashamed of. You are a very good looking young boy.” He seemed to relax as I softly stroked his cheek and gave him a warm calming smile. “I’m sure there are plenty of pretty girls at your school that would love to go out with you.”

“None of them are as pretty as you,” he blurted out instantly.

“Oh now Martin, thank you very much but you’re just saying that. There must be a lot of girls at your school your age that are much prettier than I am.”

“No ... honestly. They just ... they just don’t have what you have. You ... you’re beautiful Tanya.” I could see his eyes unconsciously look down at my chest. I figured this is what he meant when he said they don’t have what I have. I slowly took a deep breath and his eyes grew wide as those thrusting orbs swelled inside my tight sweater.

“You really think I’m beautiful, Martin?” I said as I readjusted myself slightly. I pulled the bottom of my sweater down so it stretched tightly over my tits. I then stepped so my feet were now about shoulder width apart and my little skirt was drawn tightly across my thighs. I saw his eyes glance down at the widening expanse between my legs.

“I think you’re the most beautiful woman I’ve ever seen,” he said quietly as his eyes flicked quickly up to me mine and then he once again hung his head, almost as if in shame. He paused for a few seconds and it seemed as if he was struggling with his feelings. “I ... I have to confess something.”

“Confess something? To me?” I asked curiously. The kid had my full attention now.

“Well ... I ... I...” I could hear the nervousness in his voice and I could swear I could hear his heart beating rapidly in his chest.

“Martin,” I said a little more firmly but still with a calming tone, “look at me.” He slowly raised his gaze until his sad eyes were looking directly into mine.

“Do you trust me, Martin?” I said as I gave him warm comforting look of assurance.

“Y ... yes ... I do, Tanya,” he stuttered.

“You can tell me anything, Martin. I think you’re a sweet young boy. If you want to be good friends, we need to trust each other and be totally honest with each other.” I could see the anxiety seem to drain from his body immediately as my words seemed to put him at ease. “Do you want to be good friends, Martin?”

“Oh yes, Tanya.” He didn’t stutter at all this time but his voice quivered with suppressed excitement.

“So can we promise to be honest with each other, whatever happens? Can you promise to do that for me, Martin?” I asked as I took in another deep breath and felt my breasts pushing against the straining fabric of my sweater. His eyes flicked down to my chest for just a second and then he quickly focused them back in on mine.

“Yes, Tanya. I promise.”

“That’s good Martin. It’s nice that we feel this way that we can have someone we can trust with our deepest darkest secrets.” I paused for a second to let those words soak into his brain. “Now, you said you had something to confess to me?”

“Yes ... well ... I ... I was in the mall one day about two week ago after school and I saw you. I ... I don’t know why, you just looked so pretty, that I started following you.”

“So how long did you follow me?”

“Well, at first you were just going the way I was going and then you turned into one store and I don’t know why, but I just kind of stopped and hung around until you came back out. Then you went into the lingerie store and I watched you looking at all kinds of nice stuff there. And then the next thing I knew, I looked at my watch and it must have been at least two hours since I first saw you. I ... I hope you don’t think that’s creepy.”

Well, well ... my own little infatuated stalker. This was going to be even more fun than I had hoped. “No Martin, that’s not creepy. It’s kind of sweet actually.”

“Oh good, I’m so relieved. I thought you might think I was a weirdo or something. The last thing I’d want to do is upset you.”

“You know, it’s normal for boys your age to be attracted to older women.” I stepped over to the bed and picked up a red satin corset from the pile of stuff on my bed. I remembered that this was one of the things I had bought from the lingerie store about two weeks ago. I figured it must have been the same time as the day he’d followed me. I held it in my hands and let my fingers run over the smooth shiny material as I turned back to look at Martin. “Was this one of the things you saw me looking at in the store?”

“Uh ... yes ... it was.” I could see the color rush into his face once again.

“So what did you do after I left the mall that day?” I asked curiously.

“Ummmm ... well ... I think I got on my bike and just went home.”

“And after you got home... ?” I asked suggestively as I let the words hang in the air. He really seemed to get nervous now and I saw him struggling with the thoughts inside him.

“I ... uh ... I ... I think I did my homework.”

“Now, Martin,” I said as I held the corset out towards him and shook my head back and forth like a teacher catching a naughty student cheating. “I thought we were going to be honest with each other. I don’t think you’re being honest with me right now.”

“I ... I...” he was almost trembling with anxiety now and I figured I’d better help him along before he became a total nervous wreck.

“Didn’t you wonder what I’d look like in this?” I asked as I held the sexy garment by the shoulder straps and let the full shape of it dangle before him.

“Yes ... yes I did,” he said softly.

“That’s good. That’s better, Martin. Remember, you need to totally honest with me. If not, I can take you home right now. Do you understand?” I asked him a little more firmly, but not enough to scare him.

“Yes, Tanya. I understand. I promise. I’ll be totally honest.” Excellent, I pretty much had him just where I wanted him.

“Good boy, Martin,” I said with a more comforting tone. “So, when you thought about what I might look like in this, what did you do?” He continued to look down nervously. “Look at me, Martin,” I said firmly. As he raised his eyes to mine, he looked like a little lost puppy. “So ... did you play with yourself?” As I finally asked the point blank question we had both been thinking about, I could see the color rush into face once again.

“Y ... y ... yes,” he stammered.

“Oh, that’s sweet, Martin. That’s okay,” I said as I dropped the corset onto the bed and sat down on the edge facing him.

“You ... you’re not mad?” he asked incredulously.

“No, quite the opposite. I’m very flattered actually. A woman loves to know that a young man finds her attractive enough that he jerks off thinking about her. And see ... there’s no harm in being honest. It’s a good thing.” I could visibly see the anxiety and nervousness roll off his body like a physical entity. “When you played with yourself thinking about me, did you cum?” As I asked this, I leaned back with my two arms straight behind me. I knew this position would cause my breasts to sit up like a big protruding shelf. His eyes flicked down to those big round tits and I saw him unconsciously lick his lips.

“Yes ... yes I did cum.” Now that he knew I wasn’t mad at him, he seemed a little more at ease. I still enjoyed keeping him a little nervous; then I knew he’d do whatever I asked.

“So, did you just cum that one time that night?” I asked as I let my legs roll slightly to each side. As his eyes left mine to look at the broad expanse of creamy thighs showing between my legs, I allowed my own to quickly look at his crotch. Sure enough, the noticeable bulge had returned. I was sure with this intimate line of questioning into his personal feelings towards me, he had become hard as a rock.

“Uh ... no, not just one time,” he answered demurely. I figured I’d better get right to the point.

“So how many times did you jerk off thinking about me that night?” I asked as I looked him directly in the eye.

“Four times.”

“Four times? That’s very good Martin. That makes me feel good that you whacked off that many times thinking about me. And I’m glad you were honest enough to share that with me.” I watched his eyes move down to my chest and lower to my parted legs as he stood statue-like before me. I slid my hips forward just slightly, knowing that the hem of my skirt was rising higher, enough now so that I was sure he could catch a glimpse of my white panties beneath.

“Martin,” I spoke softly to him now, “would you like me to teach you how to treat an older woman?”

“Oh yes, Tanya! I’d love that!” he said eagerly.

“Well, since you’ve been so sweet, I’d be willing to do that for you. But if you want to learn how to treat an older woman properly, you have to agree to do what I say, no questions asked ... understood?” I asked sternly.

“Yes ... yes ... I’ll do whatever you say,” his voice was rampant with enthusiasm now.

“Good. Now take your clothes off.” I was happy to see that he didn’t hesitate as he kicked off his shoes and socks, pulled off his tie, then undid his shirt and pulled it off. His young chest was totally hairless and lacked any real definition; I knew that would come as he matured. He undid his belt and pushed his pants down and kicked them aside. He stood before me now in a pair of white fitted boxers, his hard cock throbbing noticeably beneath the stretched white cotton.

“Those too,” I said as I nodded towards his underwear. Shyly, he placed his thumbs under the waistband and pushed them to the ground. As he stepped out of them and stood before me as if for inspection, I looked at him with a pleased smile on my face.

“That’s a good boy,” I said as I looked at his rock-hard erection jutting out before him. Very impressive! He had a beautiful cut cock with a large mushroom head. I was delightfully surprised at its size; it had to be close to 8” long with a good solid girth to it. I knew it was definitely pussy filling material that I would make good use of later. The broad wide head was engorged with blood and I could see a shiny drop of precum gathering at the gleaming eye and start to run sluggishly down the underside of his shaft. I could tell he was on the verge of blowing his load right then and there. I looked beside me and picked out a pair of black satin panties off the bed.

“Here,” I said as I tossed him the panties. He caught them in his hands and looked at me questioningly, unsure of what to do.

“You seem a little too excited right now for me to teach you properly. So first of all, I want you to relieve a little tension. You jerked off four times that night thinking about me. I don’t think it should be too hard for you to jerk off right now when I’m right here in front of you.” He finally looked at me with both understanding and excitement but he looked down at the panties again, a definite look of uncertainty on his face.

“When you cum, I don’t want you to make a mess all over the place. So, just when you’re ready to cum, put those panties over your cock and blow your load into them. Can you do that for me, Martin?”

“Yes Tanya, I can do that,” he said softly.

“Miss Tanya,” I said sternly.

“Wh ... what?”

“If you want to learn how to treat an older woman properly, you need to show her the respect she deserves. So you should refer to her with respect. Whenever we’re together like this, you should call me “Miss Tanya”. Do you understand?” As the idea quickly registered in his brain that this might not be just a one-off experience if he followed my instructions, a broad smile came to his face.

“Yes Tan ... I mean, yes Miss Tanya.” His eagerness to please me was now readily apparent on his face.

“That’s a good boy. Now let’s see you wrap your hand around that cock and jerk it off,” I commanded. I was pleased to see that he quickly complied as he circled his meaty cock with his right hand while holding the black panties in his left. As he started to pump that big thick cock of his back and forth, I let my thighs drift even further apart. His eyes automatically looked down beneath the hem of my rising skirt. I saw a drop of milky precum emerge from the tip of his cock and drop to the floor as his hand started to move back and forth more quickly.

“Like what you see, Martin?” I asked coyly.

“Yes, Miss Tanya!” I was happy to see that he had responded correctly.

“Come closer.” He moved a couple of steps forward until he stood right in front of my spread legs. His hand started to piston back and forth rapidly until it became almost a blur on his surging cock.

“Slow down!” As I spoke firmly, he looked at me with a confused look on his face as his hand came to a complete stop. “I know you’re excited but this isn’t a race, Martin. A woman likes to see her boy enjoying himself as he looks at her. Now, slide your hand nice and slow ... yeah ... that’s it ... nice and firm and slow ... back and forth ... yeah ... just like that. When you’re ready to cum, make sure you shoot it into those panties so I can see it.” He complied instantly with my instructions and I saw a look of eager desire wash over his face. I looked down and saw his balls drawing in their protective saw and knew he was close.