First Love

Either way, I knew I was looking forward to the end of the day. Jill and I had been dating for three months, and I always walked her home after school. At her house, we usually had up to an hour before her parents got home. When we first got together, that time had been spent talking, getting to know each other. Gradually, talking had been replaced by kissing, and then fondling. In each afternoon session, I had been making baby steps towards losing my virginity. At least that was the case before Ashley decided to take it with one big leap.

As I walked Jill home that afternoon, I felt like a baseball player. After a career of hitting singles and double, I had finally got my first homerun, and I had liked it. I knew it was time to turn up the pressure on Jill. Being a singles hitter had been great for a while, but now that I had sampled success, I wanted to round the bases again as soon as possible. After Ashley’s pseudo rejection, the last thing I wanted to do was go back to her, begging for a piece of ass. Still, I knew that if little Miss Starks wasn’t willing, that’s exactly what would happen.

We climbed the steps to Jill’s front door with her walking slightly in front of me. Automatically, my eyes focused on her ass. It was full and round, very different from Ashley’s tight, muscular butt. Jill had the kind of butt that made most guys drool when she wore tight pants. I thought about her and Ashley standing in front of me, leaning slightly forward so I could compare their butts. Almost instantly I felt the familiar stirring in my pants. Jill stuck her key in to unlock the door, and I slipped up behind her. I wrapped my arms around her slender waist and pulled her tightly to me. I started kissing the back of her neck and forced my crotch firmly against her ass, letting her feel my erection.

Jill moaned softly. “Let’s get inside before the neighbors see,” she said.

We got inside, and Jill led the way to the den in the basement. As usual, she looked spectacular. Her blonde hair was pushed back with a headband, and a pair of horned-rim glasses sat on her cute upturned nose, drawing attention to her clear blue eyes. She was wearing an ankle length black skirt, and a slate blue button down blouse. Jill’s busty frame caused the blouse to wear strangely, and all day I had been able to peak through the button holes at a light blue bra. As we descended the stairs, I could feel my cock aching to break loose from its prison.

Jill turned and kissed me as soon as were in the room. Her hand slid up my thigh and quickly began to massage my penis. Her hands were no where near as pleasing as Ashley’s, but she was getting better with practice.

“I’ve been waiting for this all day,” she said. “I’m so sorry we fought on Friday.” She paused to give me a long, passionate kiss. “Do you forgive me?”

I told her I did, even though it was partially a lie.

“Good,” she said with a smile. “That makes me happy. I love you so much, and I want to have sex with you. I want our first time to be together, I’m just not ready yet.” I told her I felt the same way, but I couldn’t help wincing inside. Partially, I felt bad because it would no longer be ‘our’ first time. Also, I was upset to hear her say she still wasn’t ready. I planned on changing that as soon as possible.

Jill guided me to the large sofa while we continued to kiss. In seconds, we were back in a familiar position. I laid on my back, while Jill straddled me. She sat her glasses on the coffee table, and playfully shook out her blonde hair. We were both aching for one another, and we began to grind our hips together, simulating sex with our clothes on. I was eager to continue with Friday night, and I discretely opened the top button of her blouse. Jill stroked my cock fiercely as I worked at the second button. Her blouse hung open as she kissed me, and I could now see the all of her light blue bra, and a large amount of cleavage. Sucking on Ashley’s breasts had only increased my desire to see Jill’s.

“Wow, you have me so turned on,” Jill moaned. “Part of me really wants to make love to you.”

Hearing those words turned my already stiff cock into an iron rod. I quickly opened Jill’s third button, and then the fourth. There were still a couple left, but her blouse was already draping open. I reach inside with both hands and began to fondle her breasts. I rubbed on the lacy bra, and Jill moaned softly. We continued to kiss and I felt her nipples standing out through the thick bra. I was ready to pull the cups down when Jill suddenly jumped.

“What was that?” she asked.

“What was what?” I said, sliding my hand back towards her bra. She jumped up quickly.

“It’s the door. I heard the door. Mom must be home.” Jill started to button her blouse, much to my dismay. I sat listening, and I knew she was right. I could now hear the footsteps on the hardwood floor above. I looked at the clock and realized we had been home for nearly 45 minutes.

“And I thought I was moving quickly,” I thought to myself.

A few minutes later, we were sitting with Jill’s mom, talking about our day at school. After that I went home, still making baby steps.

Tuesday: The school day passed in the same way as its predecessor. I spent the hours ignoring professors, dreaming about sex, playing the good boyfriend to Jill, and avoiding the hell out of Ashley. By the time the final bell rang, I was eagerly anticipating my afternoon make out session.

Jill was dressed conservatively in a long denim skirt, and a button down shirt with yellow and white pinstripes. Her blonde hair was pulled back in a ponytail, and she had opted to wear contacts instead of her glasses.

After walking home like good citizens, again we started to make out before even opening the front door. As usual, Jill was as eager as I was to fool around, she was just able to show a little more restraint. We made our way to the basement, kissing the entire way. This time, I had the top two buttons on her blouse undone before we got downstairs. Again, I noticed the improvement in Jill’s stroking technique. She had my rock hard in seconds. She was a very intelligent, studious girl, and obviously she had been paying attention to what I responded to. We made our way to the couch, and this time I was on top. Jill rhythmically squeezed my hard penis, as I gyrated my hips against hers. She moaned softly while the two of us kissed. I went back to the buttons on Jill’s shirt. I quickly undid three at once, and Jill responded by pushing my hands away. For a few minutes, we just continued to kiss. I hit the last few buttons on her shirt one at a time, being careful not to draw too much attention.

I finally got her top open, and Jill hardly seemed to notice. We continued to dry hump as I slid it off her shoulders. Jill seemed to be in a daze as she constantly rubbed my dick. She was wearing a very plain, white cotton bra. Her hard nipples stood out strongly against the fabric. I looked down, hoping the bra was a front hook, like Ashley’s had been. I was disappointed to see it wasn’t, but I continued to slowly move by kisses from Jill’s lips, to her neck, and finally the top of her cleavage.

Jill showed no signs of resisting, and didn’t say a word as I began to kiss the exposed portion of her left breast. She laid on her back with her eyes closed, still massaging by penis.

Slowly, I began to trace my tongue along the edge of the cup. Jill sighed softly. I moved my lips down a little more, and sucked on her nipple through the cotton of her bra. I could tell she was delighted by the way her hand sped up on my shaft. Jill’s breathing was becoming shallow. I was hardly an expert on female arousal, but my time with Ashley had given me a few clues.

Finally, I made my boldest move. I reached for the cup of her bra and slowly slid it down, exposing Jill’s left breast. Her strawberry colored nipple sprang free eagerly. Her tit was everything I had hoped it would be. It was completely different from Ashley’s; much larger and more voluptuous. I later learned it was a C-cup, bordering on D. The contrast between her smooth white skin, and her rough reddish nipple drove me wild. I leaned forward and flicked it with the tip of my tongue. Jill’s hand stopped moving and firmly squeezed my shaft as she sighed with delight. I ran my tongue around the nipple, and then sucked on it gently. I pulled away slowly, letting the suction tug just a big. Jill squeezed my cock harder, but I don’t think she was aware of it.

This team, it was me who heard the door first. For a brief second, I considered ignoring it. Certainly a few seconds more with this nipple in my mouth was worth being discovered? Fortunately, I regained my senses. I pulled my lips away, and Jill sat up with a dazed look on her face.

“Don’t stop,” she panted. Then she heard the door. For a second, she sat stunned. Then she snapped out of it and pulled her bra back up. “I can’t believe I let you do that,” she said. That was a good thing about Jill—she always took responsibility for her actions, and never accused me of forcing her into a situation. In a frantic state, she searched around the room and found her top. She quickly managed the buttons and had just tucked it in when her mother came into the room.

We spent the next half hour talking with her mom again, and then I headed home. I felt as if I had made significant progress, and the whole trip home was like walking on air

Wednesday: Another long day at school and the only good point was that I was able to avoid Ashley once again. Usually, our paths crossed a couple of times a week, but I still had no desire to talk to her, even though she joined Jill in my dreams each night.

On the negative side of things, Jill was wearing a pull over top instead of a button down. I tried to tell myself it was just coincidence, but I knew Jill too well. She was feeling guilty about Tuesday, and had decided to practice “defensive dressing.” It would be much harder for me work her shirt off now.

“She still looks cute,” I thought to myself as we entered the den. Something about her classy, conservative style always appealed to me. She had on a white turtleneck, a navy blue button down sweater, and a knee-length khaki skirt. Once again, we quickly found ourselves on the couch with Jill on top.

Our kisses seemed to have more passion then ever. Jill was fondling my cock like an experienced lover now, and she knew exactly how to drive me wild. As we kissed, I dreamed of sucking on her nipple again. I gently tugged on her turtleneck, pulling it out of her skirt. Jill grasped my hand and pushed it away. We kissed for an eternity, and it took three tries just to get her shirt untucked from her skirt. I started to run her smooth belly and work my way upward, and Jill responded by pushing my hand away again. I was staring to get frustrated. “I wouldn’t stop her from exposing my dick,” I thought to myself.

That’s when the idea hit me. We continued to kiss, and I shifted my hand from her belly to her thigh. It felt smooth beneath her white pantyhose. I slowly worked my hand upward as we kissed, inching beneath her skirt. I could feel the heat from between her thighs, and I gently started to brush my finger tips around her pubic region. Even through her underwear and pantyhose, I could feel Jill responding.

Of course, that’s when we heard the door upstairs once again. We straightened everything up, and again I got to talk to her mother. Afterwards, I walked home to jerk off for the third straight day.

Thursday: Again, Jill opted not to wear a button down blouse. She had on an off-white Angora sweater, with a short suede skirt. The minute we got to her house, we were all over each other. Before we could make it down stairs, she was on her back on the kitchen table. Jill’s family was wealthy, and the large bay windows overlooked the 15th green on a golf course. Her legs wrapped around her back, slowly inching her skirt upward. I looked out at the golfers on the course, wishing they would look up and see me defiling this gorgeous blonde virgin.

Somehow we paused long enough to get downstairs, not wanting Jill’s mom to walk in on us. We quickly found our way to the sofa, with Jill on top once again. We kissed softly for several minutes, and I slipped my hand under her sweater. I massaged Jill’s flat stomach and breast, but was unable to get her top off. She responded by grasping my cock.

“It’s getting harder and harder to resist,” she whispered. “I want to make love so badly.”

“Then let’s do it,” I answered. I started to pull her sweater up, and again Jill stopped me. I decided to change focus again. We kissed passionately, as my hand crept up her bare inner thigh. Her panties were soft and silky, and I could feel the warmth and dampness on them. I could also feel her thick pubic hair beneath the thin material. Recalling my night with Ashley, I slowly traced my fingers across her vagina without going in her panties. Jill almost squealed with delight. For a second, she seamed to stop breathing. Her big blue eyes opened wide, and she looked straight at me. Then she kissed me fiercely and began pumping my cock through my pants. I found the leg hole of her panties with my fingertips, and gently pulled it away, sneaking the tips of my fingers in. Jill’s pubic hair was thick, but not as course as Ashley’s. I started moving towards her entrance, when she grabbed my wrist and pulled me away. I tried to get into her panties again, but she stopped me once more. Apparently, she didn’t have a problem with me touching her through the material though.

I started to rub her ass through the smooth silky panties. Jill was pumping by cock fiercely now, and I felt like I might cum. I bunched her panties up with my hand, and started pulling on them, forcing the gusset to rub firmly against her vagina. Again, Jill gazed at me with happy, astounded eyes. Her hand tightened on my dick, and I responded my pulling harder on the panties, stroking them across her pussy. She started to pant and moan. Jill’s sounds were different from Ashley’s, but it still reminded me of Ashley’s reaction to me fingering her.

“Oh! What are we doing?” Jill panted. “Don’t stop!”

Her hand continued to work on my stiff penis. I could tell now that she was close to an orgasm. I pulled on the panties strongly, increasing the friction against her vagina. She was starting to squeal now. Her orgasm came out of nowhere. Jill’s entire body seemed to freeze up, including the hand on my dick. She stared at me with her big blue eyes, panting like an animal. “Oh! Oh, my!” she whispered. She stayed motionless, experiencing feelings she’d never known.

When it was over, she looked at me like I was a hero. She leaned forward and began to kiss my passionately. The hand on my dick started pumping out of control. She jerked it so hard I was feeling flashes of pain, but I didn’t ask her to stop. Without any warning, I felt my own climax arrive. My dick spasmed fiercely and exploded like a volcano. For a second, I felt blinded. The release was more intense and unexpected than anything I had experienced thus far. I grunted audibly.

We laid their making out for several minutes before we heard the door open upstairs. Suddenly, Jill went from a state of afterglow to panic. It seemed like she realized what had happened for the first time.

“Oh shit! What have we done?” she said. I knew she was upset because I had only heard her use profanity a handful of times in our three months together.

Jill ran around, trying to straighten things up. I untucked my shirt to hide the large wet spot on my jeans. Personally, I was still enjoying the moment. I intended to fully appreciate it, even if Jill couldn’t.

I hardly paid attention to Mrs. Starks in our afternoon conversation about school, work, and life. When I left to go home, I was as happy as could be. Jill was still a virgin, but in my mind, I had made monumental progress, and I knew that reaching my goal was finally becoming feasible.

Friday: It was another uneventful school day. For the first time in over a week, I actually made some sort of an effort to pay attention in class. What I learned was that by daydreaming the week away, I had managed to fall behind in school. If Jill didn’t put out soon, it was going to do some serious damage to my grades.

The highlight of the day was trying to hide in the middle of a large crowd when I almost ran into Ashley. I still wasn’t ready to talk to her again. The feeling of rejection still hung with me from the previous weekend. Despite my feelings, I couldn’t help checking her out from my hiding place. We had another football game after school, and the cheerleaders wore their uniforms to class when we had home games. As always, Ashley looked spectacular in hers. She was walking with another girl from the squad, and, as usual, there was a trail of guys walking with her. For a second, I thought she noticed me, and I quickly turned my head, but her group continued on down the hall without stopping.

Any part of my mind that thought Jill’s earlier change in wardrobe was just coincidence changed when I saw her that morning. Not only was she wearing a pull over style top; she was also wearing pants instead of a skirt. The temperature was in the high seventies, and as is common of autumn in the south, there were no signs of the last two chilly weeks. Jill’s sweater was baby blue and sleeveless and seemed to emphasize her exquisite bosom. She was also wearing a pair of gray slacks.

From the moment we entered the door of her house, I knew that it was going to take more than “defensive dressing” to stop me. We had both had orgasms on Thursday, and I damn sure didn’t want to backtrack any in our progress. We went downstairs and actually managed to talk a little bit before the kissing and fondling started.

We sat next to each other on the sofa, kissing softly. It was a little less frenzied then what had been going on all week. We both knew that things were getting more serious. I slid my hands down to her waist, and gripped the bottom of her sweater. Jill continued to kiss me, but slid her hands down to deter me. I had already decided that if she wanted me to stop, she was going to have to say so—I wasn’t going to be discouraged my her disapproving touch. I grasped the sweater and in one quick move pulled it upward. Jill resisted temporarily, but didn’t stop me. I lifted her arms and pulled the sweater off, revealing a shiny silver bra made of satin. Her large breasts filled the material nicely, and I could see her rock hard nipples poking out.

I pulled Jill tightly against me. She slipped her hand down to my penis, but it was obvious she didn’t want me to cum again. I kissed her gently and reached for her belt buckle. I suddenly had an urge to see her in nothing but her underwear. Again, Jill attempted to deter me with her hands, and again I proceeded. I unbuckled the pants and slowly slid the zipper down. Her panties were shiny silver and matched her bra. Even though I had undressed Ashley the week before, I was still very aroused to be taking Jill’s clothes off. Suddenly, rubbing my penis through my pants wasn’t good enough. I quickly opened my pants.

Although Jill’s mom had interrupted us several times, Jill herself had not stopped me from doing anything all week, and I was beginning to feel that I could get away for anything. Just before I pulled my penis out Jill destroyed that notion.

“No,” she said, placing her hand on my wrist. “Don’t do it.”

I was a little shocked and didn’t know what to say. For a moment I was overwhelmed with confusion, but anger quickly took its place. “Why the fuck not?” I demanded. Jill hated the “f-word” so I’d intentionally used it.

“We need to stop,” she said. “We need to stop now, or I may not be able to stop myself. Plus, my parents will be home soon. Don’t be upset”