Winter Break

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I do an ex-girlfriend a favor over winter break.
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jake1969
jake1969
57 Followers

"Can you give me a ride home?" Sheila asked.

"Sure," I replied. Trying to hide the surprise in my voice.

"Brian is in hiding," she added.

Sheila was a girl I had dated for a couple of months in the fall. The relationship had ended after Thanksgiving and now I was home on winter break from my sophomore year of college. Sheila was a year younger and at one of the local colleges. A week earlier her older brother Brian had been fired from the store all three of worked at.

An hour later, Sheila and I finished our shift at the store, and headed out into the cold to get into my car. An early 70's Dodge Dart, pretty typical car for a college kid in the late 80's. At least in my neighborhood.

It was about a 20 minute drive to the south side town where her school was at. We talked some, but it was mostly her expressing frustration about her brother and now people asking about his getting fired.

It was never really clear to me why the relationship ended. I wasn't broken up about it ending, but it seemed to just fall off a cliff. Things were going pretty good. She was planning to come up and visit after Thanksgiving. When we returned from that break things were different though. She canceled the trip and shortly after that it was clear we were through.

I thought maybe she would open up about what happened, but she didn't. Was there someone else? We were both pretty focused on our studies, I had kind of chalked it up to neither one of us really having anytime for a relationship.

When we got to her dorm I pulled into a parking place so we could continue talking. The discussion turned towards her roommates, four women the same age. Two of them she liked, one she tolerated, but the other got under her skin.

My school gave us an entire month off for winter break, but Sheila's only a couple of weeks. They had just started back, and already she was upset with this fourth roommate, Rachel. Heading into their winter break, there were two virgins in her apartment, Sheila and Rachel. But after winter break, there was only one, Sheila.

"Can you believe it?" Sheila said as she waved her hands. "Rachel fucked some guy she didn't even know."

"He was giving her a ride home for break, they got to talking about sex and then they pulled over in a rest stop and fucked."

"After the last week, that was the last thing I needed to hear. God, I am the only virgin in the apartment now."

Sheila ranted a little longer, and then she had it all out. The topic turned to me and when I was headed back to school. She decided she had better head in before the dorm security got suspicious of us being parked for that length of time and headed out to inspect.

As she opened the door to get out I said with a coy smile, "You know, I am home for another week and half if you want to do something about your problem."

Sheila didn't seem to be in a joking mode though. She responded with a "Yeah, I'll consider it," and shut the heavy door firmly. It didn't sound to me as if she would though.

About a week later, Sheila and I worked a shift together. At some point during the evening she caught me alone in one of the aisles and said, "My roommates are going home for the weekend, do you want to come over for dinner?"

I was a little surprised by the invite, but thought maybe she just needed someone to talk to. I told her I would be over.

Just before she walked away she leaned in and quietly said, "I will bring the condoms."

I am sure my jaw dropped in the surprise. Sheila bounced away and looked back to give me a smile. Not at all what I was expecting, but I was excited she made that decision. I couldn't wait for Friday night.

I showed up at Sheila's dorm around seven, she came down and met me in lobby to sign me with security. We took the stairs to the second floor where her apartment was located.

The dorms were a little different from what I was used to. These were really apartments, with a kitchen, living room, two large bedrooms, two bathrooms and even a laundry room. They also had house parents which stopped by once a week to check on things and make sure they were keeping it up.

Early when we were dating one of Sheila's roommates suggested to the house parents that the couch should be cleaned after Sheila and I had spent some time alone on it the previous weekend. Sheila told me later that while she was embarrassed by it, she also liked that it made her feel more grown-up.

Sheila cooked us dinner. Well, kind of. It was mac and cheese. Evidently this was all she knew how to cook because it was not the first time she had served this to me. But it was fun and we had a good time talking over the meal. There was some nervous energy, or maybe more just the excitement of what was to come. Neither of us seemed stressed, and there was no mention of why I was really there that night.

After eating, Sheila suggested we watch a movie. She put the tape into the player and we settled into the couch. We were both a little tentative at first, there was separation between us.

Eventually I slid over and put my arm around her, and that seemed to break the ice. She curled up to me, and we sat there in silence as we watched the movie.

A little over halfway through Sheila got up and walked down the hall to the bathroom. When she returned a few minutes later, she flipped off the remaining lights in the living room. She walked over to the couch and stopped and stood before me. For a long pause she did nothing. Then biting her lower lip, she pushed on my shoulder, as if telling me to lay back on the couch.

I did as instructed and reclined back on the couch, one leg up and the other foot still on the floor. Sheila came closer and brought one leg on to the couch so that she was now straddling me. She bent down, her face approaching mine, and for the first time in several weeks we kissed.

We laid like this for quite a while. Kissing, running fingers through each others hair, and me groping her ass through her jeans. It wasn't passionate, in a lot of ways those feelings had passed. At least the intensity had. But it was fun, and surprisingly comfortable. Just two friends sharing an intimate moment.

I was hesitant to push her too soon. I wanted to make sure this was on her terms. Eventually Sheila pushed herself up off of me, straddling me upright. She staid in that position for several seconds and stared at me as if contemplating something. Then she smiled, grabbed the bottom of her sweater and pulled it over her head.

I am sure I was smiling at this. She had great tits. Definitely above average in size, but they were firm and pert as if they were much smaller. She reached behind her back and unfastened her bra. She slowly unveiled her bare breasts as she lowered the bra from her shoulders, tossing it aside with the sweater.

I reached up to take those incredible tits in my hands. They were firm, but pliable, and were a noticeable weight in my hands.

Sheila smiled, her hands by her sides as I massaged her breasts. Periodically I would focus on her nipples, brown with small aerolae. As I rolled them between my thumbs and forefingers, her eyes would close and I could hear her breathing change.

At this point I could feel myself starting to get hard, and thought I could sense Sheila starting to grind against me. Was she ready to take it the next step?

"Do you want to continue this in the bedroom?" I asked, continuing to pinch her nipples.

She opened her eyes, looked down at me and responded with a "Yes."

I reluctantly removed my hands from her luscious tits. Using the back of the couch she pushed herself up off of me and stood by the side of the couch. I sat up, then leaned forwarded and kissed her bare stomach. My hands ran up and down the back of her jean covered thighs. Her fingers were in my hair, holding my head as I explored her stomach with my mouth and tongue.

She had had enough though. "Come on, let's go," she said, backing up and reaching out for my hand. I took her hand and followed her down the hall to the bedroom she shared with two other roommates.

We entered the room and Sheila turned on an overhead light before walking over to turn on a desk lamp.

She turned around and said, "I am already half naked. Your turn."

How could I argue. I pulled off my shirt walked over towards her and laid the shirt over the back of a desk chair.

"Would you like to help me with these?" I asked, pulling on the button fly of my jeans.

"Gladly," smiling as she responded and moved towards me.

Sheila stood in front of me, grabbed the waist of my jeans with both hands and pushed them down to just above my knees. She studied the bulge in my boxers, then looked up and smiled again.

She palmed my crouch and said, "Let's get this thing out." Then she knelt in front of me.

I stood there as she pulled the jeans down to where I could step out of them. She reached up for the boxers then and followed the same process.

I wasn't fully erect yet, but was well on my way. Shelia reached out, took my shaft in her hand and tentatively stroked it. The moment of pleasure was brief, and she stood up and backed away from me.

Sheila reached for the button of her own jeans, and freed herself from them. She now stood in front of me with only a pair of pink cotton panties. At first, she seemed nervous about removing them. After a pause she lowered them and placed them on the back of a chair with her jeans.

We stood there staring at each for a minute, not really sure what to do or say. Shelia then walked over to her bed, ducked under the bunk and laid on her side with her back to the wall. I had a nice view of her ass as she crawled in.

Once she was settled I crawled in and joined her. I leaned in and kissed her. My hand was on her hip, and this was my first feel of her skin below the waist.

She pulled away from the kiss, reached under the pillow and pulled out a string of three condoms. She ripped one package off from the string, handed it to me and tossed the other two onto a desk near the bed.

I was surprised, but I assumed we must be doing this right now then. I rolled on to my back, ripped open the foil and tossed it aside. Studying the condom, I found the right side and placed it over the tip of my cock. Sheila watched as I unrolled it down the length of my shaft.

I rolled back on my side and Sheila slid over to lay on her back. Her legs spread, quickly I was over the top of her on my hands and knees. I lowered myself down on to her, and reached down for my cock. I rubbed it against her pussy, spreading her wetness, and searching for the opening.

I lodged the tip of my cock inside of her. I couldn't see her face, but by her sounds I could tell there was some discomfort. I paused, giving her a chance to relax a little. Evidently none was needed though. I quickly felt her hand on my ass pulling me deeper into her.

She was very tight, like she was squeezing me with her hand. Once my entire length was inside of her, I could feel her finger nails digging into my butt cheeks. I decided to be still until she relaxed a little more. After a few moments she extracted her nails from me, and I began to slowly thrust into her.

Her sounds expressed more pleasure as she brought her legs up towards her chest. I was plunging deeper into her, her hips moving up to meet my thrusts. I could feel the heels of her feet on the back of my thighs and her hands in my hair. My thrusts became quicker, going at whatever speed I desired. She was simply along for the ride at this point.

I could feel cum in my balls starting to rise up. Sheila's moans of pleasure spurred me to a faster pace. No more drawing it out, I needed to cum soon. I brought myself up to a position where I could thrust even deeper. From her quick shout it was obvious Sheila was caught by surprise as my cock was buried to the hilt inside of her. Within thirty seconds, I was done. My pace slowed, and I could feel my cum filling the end of the condom as my cock twitched inside of her.

My body became still as I tried to catch my breath and recover from the release of energy I had just experienced. I tried to support my weight above her, and could hear her heavy breathing as she too tried to recover. Slowly I felt her legs release their grip on me and until they came to rest back on the bed.

I slowly extracted myself from her. Kneeling between her legs, and trying not hit my head on the bunk above, I looked her in the eye.

"You ok?" I ask.

"Sore," Sheila responded, "but good. God you are not small!" She smiled as she said this.

I exited the bed and stood by the side. Sheila's eyes were glued to my still fairly erect cock, and the tip of the condom that was still swollen with cum. I grabbed the base of the condom, pushed all the cum to the tip with my other hand. The reservoir filled with the white fluid and expanded even more.

"Is that a lot?" Sheila asked.

"It is for me," I responded.

The look on her face seemed to express great satisfaction in a well accomplished task. I slid the condom off and then walked to the bathroom as disposed of it.

When I returned to the room, Sheila was lying on her back with eyes closed. Ahand on a breast, fingers tweaking the nipple.

I laid down in bed beside her.

"Let's see if I can take away some of that soreness," I said.

I placed hand in between her legs and began to gently rub her mound and labia. They were still wet and swollen and easy to manipulate. Sheila responded quickly with moans of pleasure. I avoided penetrating her to prevent causing any more discomfort. After a few minutes I switched to a single finger and began to focus on her clit.

She acted surprised at first, I couldn't tell if that was really the case, or if she was simply over sensitive. I circled her clit with my finger, then quickly slid it down the length of her wet lips, and then returned to the clit. Each time I removed my finger from her clit, she let out a quick gasp of air.

After a few more minutes I decided it was time to try and finish her off. I stayed focused on her clit, and she responded with a loud exclamation as she bucked her hips in the air. I kept my finger on her clit as her hips began to twitch, and unintelligible noises came from her.

Sheila's orgasm finally subsided and she grabbed me around the back of my neck and pulled me in for a crushing kiss. Her tongue slipped into my mouth and probed for mine.

Finally she relaxed and I was released from her grip and allowed to lay back down on the bed. We laid there naked and talking. Surprisingly it was extremely comfortable. Really no talk of what we had just done. Just discussion of school, new experiences that awaited us, and people we worked with.

There was some occasional touching and caressing. It wasn't sexual though, at least at first, just two people enjoying the nakedness of each other. I began to lightly run my finger tips down the back of her ass and thigh and this must have ignited something in her again.

Sheila pushed me onto my back and grabbed my cock. She leaned over and kissed me as she she stroked me.

"Are you fully recovered?", she asked.

"Yes," I replied.

"Can I get on top?", she asked.

"Of course," I replied, smiling now.

I watched Sheila as she got up out of bed and walked over to her desk again. She grabbed the pair of condoms and separated the packages with an audible rip. She smiled and wiggled the square package at me as she walked back to the bed.

"Can I put it on you?" Sheila asked as she stood at the side of bed.

I nodded my approval.

She sat down on the edge of the bed and started stroking my cock again. For the next two minutes she didn't say a word. Just slowly stroked it as if she were studying its shape and texture. Coming out of her thoughts, she grabbed the condom again and tore open the package. Pulling the latex disk from its wrapping she studied it for a moment.

"Is there right way?" she asked.

"Yes, the side where you can see it rolled up faces up," I responded.

"Ah, yes!"

Taking my shaft in one hand, Sheila placed the condom on top of the head and pushed down. At first, there was a little difficulty unrolling it. Once it was past the ridge of the head, she easily unrolled it the rest of the way.

Once the condom was on, Sheila quickly crawled onto the bed and straddled me. She couldn't quite sit straight up because of the upper bunk bed, so she leaned over with her hands pressed against my chest. She lowered her hips onto me, and slowly rocked back and forth. I could sense she was already very excited by how easily the cleft of her sex glided over the length of my shaft.

I reached up and cupped one of her breasts in my hand. It was firm, and I could feel the stiff nipple in the palm of my hand as my fingers lightly stroked the soft flesh. I watched her face as I played with her breast and she continued to slowly grind away on my shaft. Her eyes were closed, her breathing was heavy and mouth partially open. Her face tensing up periodically. I tugged at her nipple as I pinched between two of my knuckles, and she let out a groan.

Grinding against my cock didn't seem to be enough for her. Sheila lifted up off of me, and reached between her legs to grab my cock. I could feel her rubbing it against her sex, searching for her opening with the head. Finally she found it lowered herself onto me. She took it slow, and appeared to wince a couple of times. When she had taken my entire length, she relaxed and started to slowly move her hips.

Sheila opened her eyes and smiled, "You feel great."

"You feel pretty great yourself," I responded.

She was sliding up and down my length and it felt as if she was tugging on me as she did it. After a few times she would stop and grind her clit against me for a few seconds and then repeat the process. I would raise up my hips to meet her some of the time, but was careful to not spoil her fun.

Sheila continued this process for probably close to ten minutes. While she did, I enjoyed the feel of her skin, her breasts, her ass. It was all mine to experience.

Eventually she stopped sliding up and down my cock and resorted to just grinding away at me. Her rhythm picked up speed, and I grabbed hold of her hips, helping her with the motion. Faster and faster she gyrated on my cock, exclamations of pleasure coming from her.

And then suddenly, she collapsed onto my chest. Her insides still tugging slowly at my cock, but much slower now.

She kissed me, "Thank you."

I just smiled. My fingers running down her back, over her ass, and then back up towards her neck. She extracted my cock from her tight puss, and rolled over on to her side facing me. She stared and smiled at me. I really wanted to crawl on top of her again, but I wasn't sure what she was thinking.

"Get out of bed," she instructed.

I paused, not quite sure what to say, "What?" is all that came out.

"Get up and stand by the bed," she said again.

Reluctantly I slid my legs over the edge of the bed and then sat up. I turned back, hoping she would change her mind and invite me to stay. She just smiled, cocking her head as if she was saying to keep going.

I stood up, careful not to hit my head on the upper bunk, and turned around so that I was facing the bed again. The top of the upper bunk's mattress was about even with my chin. I stood back far enough so I could still see into the lower bunk. My arms out in front of me, supporting myself against the upper bunk's frame.

Sheila laid there for another moment, then slid her legs around to the edge of the bed. When she was done, she was sitting on the edge the bed, legs straddling mine, and my cock pointed right in her face.

She took my cock in her hand, studying the underside as she slowly stroked it and considering how to remove the condom.

"Just roll it off," I stated.

jake1969
jake1969
57 Followers
12