Women in my Life

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Christine was shy and a virgin; April was neither.
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Leader12
Leader12
968 Followers

I met Christine two weeks before the dormitory opened our junior year. Both of us, along with 30 other upper-class and graduate students, had been selected to be Resident Advisors on the floors of the dorm. We had two weeks of training and bonding sessions before the students showed up. Like Christine and me, many of the new RAs had lived in this dorm as Freshmen or Sophomores, so they were familiar with the basic layout of the place. But some were new to the facility. The training included information about the building itself, some procedures that had to be followed, rules, safety procedures, etc.

Some of the other training addressed serious issues, like mental health issues, drug addiction, and alcoholism. The administration didn't even try to say silly things like 'no drugs or alcohol'; it was assumed that some people would smoke grass in the privacy of their rooms. The training was directed to those with serious problems and what to do if there was an overdose or possible alcohol poisoning. Discussions about suicide prevention were also included.

Most of the time, however, was much lighter than those serious topics. There were a number of sessions for people to get to know each other and bond into a cohesive group.

During the early days of our training, I was surprised that Christine even applied to be an RA, and I was even more surprised she was hired. She seemed incredibly shy, and this job required interacting with students - including students who were shy themselves. But when we were in smaller break-out groups, or when I got the chance to talk to her one-on-one, she seemed like a different person. I found out she was an incredible listener and offered some really great advice. She was majoring in Psychology, and she took her studies seriously. When we did simulations of kids with issues, she asked great questions and displayed incredible empathy.

I found her shyness rather charming, but I found her insight into human behavior absolutely alluring. It also didn't hurt that she was really cute. I later found out she had run cross-country in high school, and she kept up the habit of near-daily jogging ever since, giving her a lean look with strong, long legs. She had a small, cute nose, beautiful, blue eyes, and blond hair that went half-way down her back. I loved it when she put it in a ponytail that she looped through the back of a baseball cap.

I always tried to sit next to her at our sessions, and after a few days, she would even save me a seat. We started getting together in our limited free time, usually just going for a walk and talking. Before the end of the two weeks, we were a couple, and I couldn't have been happier.

The first few days after the dorm opened for students, we were both really busy and didn't get to spend too much time together. At the end of the day we'd try to meet for a little bit, sometimes grabbing a latte at the Starbucks that was in the lobby of the dorm, but we didn't have much time to really get away. After classes started, we were again busy, trying to help students navigate life on their own for the first time. It was exhausting but fun.

By the second week of classes, everyone seemed to be getting comfortable in their new routines, so we were able to spend more time together. We'd usually eat together in the dorm, but we'd sometimes go to a (cheap) restaurant on campus for a break. I really enjoyed every minute we spent together, and I knew Christine felt the same way.

About the only area that I wasn't totally thrilled with had to do with intimacy. And I'm not just talking about sex, I'm talking about ANY kind of intimacy. It was a long time before Christine even felt comfortable making out. For a long time, she just gave me a simple kiss on the lips - with a closed mouth - when I left, and that was it. I had learned she came from a very conservative family and never dated in high school, and she rarely went out her first two years at college.

We had been dating for about five weeks and hanging out in her room when I walked over to her. She was sitting on her bed, and I held out my hands. She put her hands I mine, and I pulled her to stand up. She had a confused look on her face, but she was smiling.

"What's up?" she asked.

I put one hand behind her on her waist, one hand behind her head, and put my lips on hers. I kissed her hard, and she whimpered a little. She moved a little, not exactly trying to get away, but clearly displaying a little discomfort. Then I opened my mouth and licked her lips. She pulled back and looked at me. I pulled her head forward and did it again. Once more, she pulled her head back and looked at me.

"Open your mouth. It's okay," I said. "It's what people do when they like each other."

She continued looking at me for a couple seconds. Suddenly, she grabbed my head, pulled my head towards her, and kissed me. Unexpectedly, she opened her mouth, accepted my tongue, and kissed me like we'd been doing it for years. Her tongue slipped into my mouth, and I almost started laughing at her sudden aggressiveness. But I certainly didn't want her to stop.

We kept this up for quite a few minutes, sometimes slowing down while we kissed and other times moaning with pleasure. Wondering just how far she was now willing to go, I slowly slid my hand up her stomach until I touched her breast. She quickly pulled her head back, and I froze. Without saying anything or pushing my hand away, she slowly started kissing me again. I took this as permission and put my entire hand over her breast for the first time and gave a gentle squeeze. The sweet moan that I heard, along with having my hand on her breast, got me extremely excited.

I continued caressing her breast and felt her nipple pushing through her tee shirt. I gently pinched it, bringing a louder whine. When I slipped my hand under her shirt onto her bare stomach, she froze and grabbed my hand.

"I don't know, Ken," she said, but with a breathy voice that implied she was excited and wasn't sure she wanted me to stop.

"It's okay, Christine. Let me make you feel good," I said. I didn't say 'please' because I didn't want to sound like I was begging. I also didn't want to make her do something she really didn't want to do and have her hate me for it later.

She looked at me for a couple of seconds, then removed her hand which had grabbed mine, and put it behind my neck. She leaned in to resume our kissing, so I continued moving my hand up her stomach and over her bra-covered breast. As I gave a very soft squeeze, she released the most beautiful sound I could have heard.

"Mmmm", she quietly cooed, as I continued playing with her breast. I used my free hand to pull her waist against me, making sure she could feel my hard dick. I was surprised - but very happy - when she moved her hips just a bit to grind against me. Her nipples were very hard and easily pushing through her bra, and her groaning indicated she liked it when I squeezed them. After quite a while of enjoying our first real make-out session, I pulled my head back, removed my hand from under her shirt, and put both hands on her waist.

"I want to take off your shirt, okay?" I asked.

She was silent for a couple of seconds, never taking her eyes off mine.

"I don't think so," she said. "No boy has ever seen me like that. I don't think I'm ready."

"Maybe no boy has ever loved you, either. But I do, Christine."

It was clear we loved each other, but that might have been the first time I explicitly said it. And I know the L word has been used for a hundred years just as a line to get into a girl's pants, but that's not what I was doing. I really loved her.

A broad smile inched across her face.

"I love you, too, Ken."

To my pleasant surprise, she held her hands straight up. I grabbed the hem of her shirt and lifted it up and over her head. I tossed it on the bed.

Christine's breasts looked wonderful in her white, lace bra. They weren't huge and they weren't small; they were perfect. I could faintly make out the darker coloring of her areola. I'm sure I looked like an idiot with the gigantic smile I was wearing.

"You're so beautiful, Christine," I said. "All of you."

As I leaned in to kiss her, my right hand returned to her breast. After a short kiss, I bent down and sucked her free nipple through her bra, causing her to gasp. I reached around to unhook her bra, and she didn't resist. When I slid the straps off her shoulder and pulled it away to expose her breasts, I couldn't contain my excitement. Although I had seen more than one set of naked breasts in my life, I was hardly the big stud on campus who had slept with a hundred women. Seeing each new naked woman was incredibly exciting, and Christine's body was probably the nicest I had ever seen. Her areolas were dark brown, and she had thick, currently hard, nipples.

"Oh, god, Christine. Your body is incredible. Just incredible."

I quickly lowered my mouth to one nipple and placed my hand on the other breast. Finally seeing and touching her naked breast had me unbelievably excited, and I grinded my hips and hard dick against her. Happily, she pushed back against me.

This was a major moment for Christine. I was the first guy to see or touch, let alone suck, her naked breasts. She grabbed my head and moaned loudly. She later told me she almost came just from the incredible stimulation of her nipples.

We continued making out for a long time like this. Finally, I had to decide if I was going to push the limits even further. I honestly wasn't sure which way it would go.

"Let's lie down on the bed," I said.

I thought Christine was going to object when I saw her start to say something, but she didn't. Instead, she said, "Take off your shirt. I want to feel you against me."

I ripped the shirt off my head in record time. Christine lay on the bed, and I lay next to her. Then I rolled her on top of me. I loved feeling her hard nipples push against my chest, and my hard cock push against her stomach. We resumed kissing each other, with my thumbs rubbing the sides of her breasts.

After a few minutes, I moved my hands onto her butt and pulled her against me as we continued kissing. I kept squeezing her butt cheeks through her sweatpants, and sometimes this made her thrust her hips into me. I slipped my right hand under the waistband of her pants. Pushing down against her skin and moving my hand down towards her butt, I ended up going into her panties and had my hand on her bare ass. We both let out a soft groan. Since she didn't put up any resistance, I did the same with my other hand.

With my hands on her ass and her naked breasts against my naked chest, I pulled her against my hard dick while I massaged her butt cheeks. I had been hard and excited a long time, and the combination of all the skin-to-skin contact and her grinding against my dick had me worried I was going to come in my pants. I needed to change something, and I had to find out how far she was willing to go.

I reluctantly pulled my hands out of her pants and rolled her off of me, onto her back. I smiled broadly as I looked at her face and breasts, and I used just one finger to make slow circles around her areola.

"Do you have any idea what you do to me?" I asked.

She smiled at me.

"You make me feel awfully good, too," she said.

"Christine?" I said softly, as I slowly moved my hand down her stomach and toward the waistband of her pants, with just two fingers making contact. Her stomach clenched as my fingers moved over it. When I hit her pants, I moved my fingers back and forth just above the pants, again causing her stomach to clench and release a couple of times.

She looked at me with the sweetest eyes, but I wasn't 100% sure how to interpret her look. She wasn't exactly smiling, but she wasn't showing fear. We looked at each other for what seemed like a long time but was probably only a few seconds. Then I saw a just the slightest, most subtle nod of her head, and I broke into a huge smile. I leaned down to put my lips on hers as I slipped my hand into her pants.

Her body twitched as my hands moved over her panties. I cupped her entire vulva and pressed gently. Christine whined and lifted her torso a little. I used my middle finger to gently press between her lips, pushing the wet panties into her. She gasped, but she didn't try to stop me.

I slid my hand up and then into her panties. Again, Christine clenched but then lay flat. As I moved my hand down, I felt her pubic hair. I circled my finger on her mound for a bit, causing Christine to smile. As I continued moving my hand down, I suddenly encountered perfectly smooth skin. I spread my index and middle finger, putting one on each side of her lips and gently brought them together. A soft coo came out of her mouth. Moving my middle finger directly between her lips changed her sweet coo to a sudden gasp. I gently moved my finger up and down against her soft, wet, most-intimate area.

Finally, I let my middle finger drop down. I bent it and slipped it inside her soaking pussy. Christine jerked her hips up as she cried out. I stopped for a second, letting her get used to the feeling. Her hands were clenched in fists as she breathed deep and loud. After a couple of seconds, I slowly stroked my finger back and forth, bringing constant moans from her. I was incredibly excited, as was she.

After a minute of fingering her slowly, I pulled my finger out and moved it up toward her clit. When I rubbed against it, she yelped and grabbed my wrist. She didn't pull my hand away; she just held it. I rubbed her clit a couple more times, and she was clearly unbelievably excited. I figured now was the best time to make one more move.

I pulled my hand out of her sweatpants, and I was pleased when she yelled, "NO!"

I smiled to myself as I grabbed the waistband of her sweatpants and started to pull them down. I was hoping Christine's desire for me to continue rubbing her would cause her to throw caution to the wind, and I saw I was right when she lifted her hips so I could pull the pants down to her knees. Without pausing, I quickly reached up and grabbed the waistband of her panties and pulled them down, too. Almost reflexively, Christine lifted her hips again, and I pulled them down. I then pulled them, along with her pants, off her feet.

I can't describe my excitement at finally seeing her - the girl I loved and the girl I fantasized about - naked in front of me. I wasn't sure exactly how she felt about it, but I wanted to quickly get her mind back to the pleasure she was receiving. So, while I wanted to just stare at her naked beauty, with black, untrimmed pubic hair on her mound but completely smooth lips, I quickly placed my index finger back into her pussy, causing a sweet moan. I licked the index finger of my other hand and used it to gently rub her clit.

As Christine returned to her excited pose - eyes clenched tight, hands shaped into fists, and head thrown back - I pulled out my finger and licked the opening to her pussy.

"NO!" she screamed. "Please don't. Put your finger back."

Though I was disappointed I couldn't eat her, I was still thrilled to be able to work her up toward an orgasm. I loved being able to look at her, finger her, and rub her clit.

As I rubbed her clit a little harder and faster, she was thrusting up into my hands and quietly grunting with each thrust. I leaned over and took her nipple into my mouth, bringing a louder groan.

I increased the speed of both of my fingers until Christine suddenly grabbed the wrist of my hand that was stroking her clit, pushed her body into my hand very hard, and started shaking on the bed. I continued flicking my tongue on her nipple, rubbing her clit, and fingering her as I heard her softly cry, "oh, fuuuuuuck". I continued in this position throughout her orgasm until her body suddenly lay flat on the bed and she pushed my hand away from her clit. I slid my finger out of her pussy and pulled my face away from her breast. I quietly stared at my beautiful, naked girlfriend as she tried to catch her breath.

After a minute, she opened her eyes, looked at me, and smiled.

"WOW!" she said.

"Thank you for letting me do that," I said. "I loved making you feel good. And in case I forgot to tell you, you are absolutely beautiful."

She smiled as she said, "Ken?"

"Yes."

"Can I see your penis?"

I laughed for a second.

"Penis? What are you, in medical school? You mean my dick? My cock?"

Christine laughed, too.

"Sorry... I've never used those words. Actually, I'm not in a lot of conversations where it comes up."

We both laughed.

"Can I see it?" she asked again.

Though I was rock hard when I was fingering her, my dick had deflated a bit. I would have preferred if the first time she saw it, it was as big as possible. Yes, every guy without a porn-sized dick is worried that a woman won't think it's big enough.

"Of course, but you have to be the one to take off my pants," I replied.

Chrstine smiled. She moved down the bed, unbuckled my shorts, and unzipped them. As she pulled them down, I lifted my hips. She pulled them off my feet, leaving in my boxer-briefs with a semi-hard dick. She stared at the bulge for a couple of seconds. Just lying there, with Christine, naked, pulling off my pants, I started to get harder.

"Would you do me a favor?" I asked.

She nodded.

"Please rub it for a few seconds before you take off my underwear."

Christine bit her lower lip and tentatively put her hand on the bulge. It was the first time she had every touched me, and it had the anticipated effect. She gave a little rub and then a squeeze, causing me to groan.

"Okay, take them off."

Cautiously, she put her hands in the waistband and started to slide them down. As soon as she got low enough, my erection popped up and Christine froze, just staring.

I was pretty sure it was the first live dick she had seen, but certainly she had seen some in porn. I hoped she wasn't mentally comparing my average dick to the 7- and 8-inch dicks the porn stars have. She continued just staring for a few more seconds.

"Wow," she said.

I didn't think she was going to follow that with "it's small", so I was feeling okay.

"It's really nice. Can I touch it?"

'FUCK YES YOU CAN TOUCH IT. PLEASE TOUCH IT' I thought, but, instead, I just said, "of course."

She wrapped her hand around it, which caused me to groan. This made her smile. She started stroking up and down. Yeah, I thought, she's seen porn. Thank god.

After a couple of minutes, I asked her to lie down on the bed. She continued stroking my dick as she lay down. I kissed her and moved my hand to breasts, squeezing them and pinching her nipple. Christine made sweet "mmm" sounds. I slid my hand down her stomach, over her pubic hair, and rubbed her entire vulva. She twitched a little and made more sweet sounds. I was surprised that she was again fairly wet. I slipped one finger into her pussy. She softly cried out as she thrust her hips forward, but never stopped stroking my dick. She started moving her hand faster, and I was incredibly excited.

As I stroked her pussy, she got wetter and wetter. She was also breathing very heavily.

"Ken?" she called, breathily.

"Yeah?" I replied through my own quick breaths.

After a short pause, she said, "put it in me."

My eyes popped open. Did I hear her correctly?

"Christine, do you mean..."

She cut me off before I finished. She had a strained smile on her face.

"Yes. Make love to me. I'm ready."

"I have to put on a condom," I said, planning to get one out of my wallet.

"Top desk drawer," she said, surprising the shit out of me. But I wasn't about to question her now. I quickly went to her desk and grabbed one. I put it on and climbed on top of her between her legs.

"Are you sure?" I asked one more time.

Leader12
Leader12
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