Helping My Roommate, Kelsey
This is something that happened just out of the blue one night, as it was not planned and it's evolved into something really interesting. It's basically turned into a lesson of sorts. The first four parts of this story happened in consecutive nights. The last part happened six days (nights) later.
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It's important to note that Kelsey is straight as an arrow, saved her virginity until she got married, had never masturbated before in her life, had never had an orgasm before she got married, and was actually disgusted by Monica's bisexuality when Monica and I had first started talking to each other.
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It all started one night when I was up late, bored and a bit horny. I went into a chat room and happened upon a guy who I started talking to and since I was in the mood I was in, I decided to go along with his ideas of doing what he told me to. To shorten that part, it ended up involving Kelsey as she was still up at the time, so he got me to call her into my room. After that, I used a ruse about talking to some guy from class and an elaborate dare to get her to stay until I asked her to leave. I was naked under my blanket and laying on my stomach. I started softly touching myself and made sure the blanket 'accidentally' fell off me, so she got to sit there and watch me masturbate.
He got me to give her the computer so she could talk to him while I was having at myself. He had her touch me, by running her fingernail along my spine a few times while I was masturbating. After my orgasms, she stayed and I ended up getting a little turned on again when I noticed her nipples poking through her shirt (she was only wearing a night shirt, pj pants and panties). I'm actually fascinated with her breasts, which will become even more obvious later in this story. I straddled her lap and held onto her, I rubbed myself along her thigh to get myself off one last time before sending her to bed, with a decent wet spot on her pant leg.
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The next night I got her in under the same ruse. Talking to the same person, he got her to undress down to her panties (she had been wearing a tank top & yoga pants in addition to her panties) for me after I stripped down completely naked right after she came into the room. This time she didn't really show that she cared about me being naked, since what she'd seen the night before. She was a bit shy and nervous about being mostly naked in front of me.
I once again straddled her, both legs this time, so her thighs were actually pressed together. I kind of held her and whatnot, she ended up closing her eyes after I did the fingernail thing on her spine a few times. The guy I was chatting with suggested I check her panties to see if they were wet. When I did, I found them to be slightly damp, and at this point she grabbed my thigh and squeezed.
After getting a bit excited now myself, he suggested I rub her under her panties, but I had to re-position myself to do so, so I stood up and whispered, "I'm taking these off" into her ear as I pulled her panties down. All she did was softly gasp, and kept her eyes closed. I put my leg between hers and straddled her left thigh this time. When I was settled back down on her, I slipped my hand up her inner thigh and gently slipped a finger into her. As soon as I touched her thigh she latched onto my thigh again, digging her nails into my leg.
I pushed my finger into her, and got it all the way in, but my gosh is she tight. Like, amazingly tight, whereas one finger was all I could get in there and I didn't even have to try another to know this. After getting a feel for her, I quickly located her gspot, pressed on it, then started massaging it. She started breathing faster and letting out soft sounds, such as moans, groans, little mewling sounds and squeaks. I just jerked my wrist back and forth to stimulate her gspot, much as I'd learned from Monica.
Then, not long after I had begun this, I had her wet enough to slip a second finger into her. Then shortly thereafter, she started orgasming. I honestly believe she had multiple consecutive orgasms. When she started cumming, she dug down into my thigh and buried her head against my shoulder. While I was playing with her, I rubbed myself on her thigh and had a nice little orgasm of my own while I was getting her off, this time leaving a sticky mess on her bare thigh. After that I helped get her dressed and back to her own bed, as she was shaky and couldn't really walk on her own. I actually kept her panties though, not that she even noticed.
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The following night I wanted to see about continuing. I ended up talking to the same guy and got her in my room. This time things took a 180, as soon as she got into my room, she stripped out of her pj pants and cami and sat in my chair naked. I was wearing my ball shorts and sports bra at the time. Her and I had talked earlier in the day about what happened the night before. She wasn't upset at me at all, she even asked about learning more and we talked some about masturbation and my relationship with Monica.
So after that, I got naked to make her feel more comfortable and the third party (the chat guy) wasn't necessary, as she was willing and able on her own now. We sat and talked about a lot of stuff for about a half hour while we were both naked. She wanted me to teach her how to do what I did to her the night before. To help her find her gspot, and explain how she could teach Steven (her husband) to do the same thing.
So I set up a plan, with us sitting side by side on the bed. I reached over and located her gspot for her, then told her to do the same with me. She actually didn't have much trouble locating mine, and I had to stop her before I went off the deep end quickly. After that I told her to find hers and have fun with it. She followed my instruction and really got after herself.
While she was masturbating for the first time, I got to massage and play with her breasts and nipples. I am so amazed by her big beautiful breasts, they just pull me in and entrance me. It didn't take her too long to bring herself to an orgasm herself. She fell back on the bed, breathing heavily, panting and trying to regain her composure.
When she was sitting up again, this time I had her massage my gspot and I did so to hers, the goal being to see who could orgasm first. Of course, I came before she did, a couple times. It didn't take me too long to get her off after and when she climaxed, she passed out on my bed. I had forgotten to put a towel down, so there were two decent sized wet spots on my sheets all night. Including the one I made after helping her back to bed once again.
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The next night, following her husband going to bed, she decided to stay up. She actually showed up in my room without me asking for her this time. She said she wanted to talk to me about things and ask me some more questions. We ended up discussing masturbation and my collection of toys. I was on the computer when she came in and was talking to some people I've developed a dialog with over the past few days. A certain someone (you know who you are) offered their hand in guiding where the next step in all this would lead, so I figured it wouldn't hurt.
He respected the boundaries Kelsey and I had set forth a couple days before, in which there would be no kissing, she would not kiss or lick me anywhere, and I would not kiss or lick her anywhere but one specified area that she approved of. So after all the discussion, he suggested she look over my 'collection' and pick one out to use on her, in which she picked the one I figured she would. That would be my small glass dildo.
He had her undress while I was out of the room when he was talking to her. She picked out the toy after I had got back. I got undressed myself shortly after coming back as I know she is more comfortable with me being naked when she is. We got ourselves situated on the bed and it started out by having her use her finger(s) to find her gspot again. She didn't have any trouble at all this time, and he suggested I have her find mine as well, and of course, she didn't have any trouble with that either.
So she basically fingered us both to multiple orgasms while we sat on the bed together. Before she put her fingers in me though, I did get a chance to kiss, lick and suckle on her beautiful nipples. After our orgasms, I actually licked her fingers clean, all of them. It was the first time I got a taste of her, and it was pretty awesome.
Next, we finally got to using the toy. At first, I slipped it in here so she could get used to it and know what it felt like to have something like that inside of her. After I showed her how to angle it so it slid against her gspot, she learned how to use it on herself. I suggested she try and use her other hand to rub her clit, which I had helped her with since she'd never actually touched it knowingly before.
She soon got into a nice little rhythm and she let me play with her big, beautiful breasts while she masturbated herself for the first time with a toy. She had another set of multiple orgasms, at least, that's what I believe I saw. Her sticky white cum (much like mine) was coating the dildo when she was finished. I tried to get her to take a taste, even just a small one, but she didn't want to, so I didn't press the issue. I would've licked it clean myself, but I didn't want to freak her out or anything, so I refrained from doing so.
When she was okay to move again, she got dressed and was able to make it to her room on her own this time. She didn't pass out, so I think she's getting used to herself, or maybe we're over doing it right now, ha. I was exhausted, so I didn't do anything to myself before bed, I just tossed the towel in the hamper and curled up under my blankets naked and went to sleep. I did wake up wet this morning before class, and had it running down my thighs on the way to the bathroom.
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The night following we had a volleyball game that almost got cancelled, but didn't. Kels and I are on all the same intramural teams, so we play together. It was a late game and all three of us got back after 11. We all hung out in the living room watching TV for a little while, but I got bored of that and went into my room not long after. I should mention that in talking to Kels earlier yesterday, I had asked if she'd be interested in taking a shower together, which was suggested by someone I talk to on here (you know who you are). She said that would be okay, so we decided the next time we had to shower, we'd do it together, but we had to wait until Steven wasn't around.
Sometime around 3:00 Kels popped into my room, in her undies no less (she was wearing a black sports bra and a purple thong) and asked if I was ready for the shower, that Steven had gone to bed. So I got my stuff together and we went and took a shower together. This time it most definitely wasn't like the previous nights. There was no sexual contact between us, the closest that got was me holding her from behind and massaging her big beautiful breasts. We helped wash each other, I actually got to touch her butt for the first time, her butt is bigger than Monica's, ha.
I had to shave my crotch, and I showed her how I do it, how Monica taught me how, to make sure I get most of the hair, which she found pretty helpful. We didn't touch each others privates at all. We concluded our shower and went back to our rooms covered by only our towels.
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After an amazing Valentine's night, a great, but tumultuous Saturday, I have another story to share about Kelsey. Before last night, we had only showered together once, and JUST a shower (she also held me to comfort me because of how I was feeling Saturday night), and went to the pool on Sunday, since the last time anything went on between us. So, I bet you're all waiting to hear the dirty details from last night though, so here we go.
Yesterday evening Kels told me she wanted to talk to me about some things. We had a little bit of a chat then, but that was it for then. Later, after I had already gotten naked, simply because I felt like it. Yes, I spent a few hours walking around the apartment naked just because I wanted to. We discussed masturbation, and, mostly, vibrators. Since she's never experienced one before, she wanted to know what it was like and if I would let her use one of mine.
She was wearing something that really caught my eye this time. Kels had on a pink cami spaghetti string nightshirt that really fit around her upper body, and it was very clear she had a headlight situation going on under there. She had on sky blue pajama shorts that I could tell had been purchased before her waist size went up some, as they didn't leave a whole lot to the imagination, especially from the backside.
After all the talk, and showing her which battery operated toys I have, I decided to have her use my little white and blue pocket rocket, which is the same one I use for my video on here. Got her to take her top off, which at this point she has no issues with whatsoever. I turned it on and pressed it against the top of her slit through those thin little shorts. She gasped, jerked and flinched at the contact, which is what I expected and why I didn't want to try direct contact with no barrier to start with. I only needed to hold it for a little while before she got the message and took over herself.
After she did, I leaned down and got to massage her breasts and suck/suckle on her pretty pink nipples. I got to see her little shorts become increasingly saturated, which I enjoyed very much. After that, I knelt in front of her on my knees and started to simply knead, rub and massage her breasts. I grabbed one of her hands and brought it between my legs, however, she opened her eyes when her hand made contact with my crotch, looked me in the eyes and moved her hand up to massage my breast. The reason for this is because she knew I was sore between my legs from what happened Saturday, as she was the first person I told about all that. Kels would never want to do anything that would cause me discomfort or pain, so that's why her hand went up.
About 15 minutes later I told her to stick it under her shorts and press it directly against her clit. It only took her five minutes of that to begin to orgasm. When she did, she squeezed down on my breast, a little hard, but it was okay. Her body tensed up, she made a little yelp/squeak sound as her breath went out of her, her stomach/abdomen spasmed and her legs started twitching. Again, I'm pretty sure she had a couple of consecutive orgasms.
After that, the crotch of her little shorts were soaked. Almost as wet as my shorts were Saturday morning. She laid back on my mass of pillows and recovered for a bit. When she sat up and was able to look at me and speak again, she took her shorts off for me and handed them to me. I decided to just go for it and started licking the wet crotch of them in front of her. Thankfully for me she didn't run away, but she scrunched up her nose at me, said I was a weirdo and was being 'silly' as she put it.
The next thing I did was put her shorts on, as they were still pretty wet from her. I must say, there was room in them for me, and I have a big ass, and they were TIGHT on her, so tight her butt cheeks where spilling out the back/bottom of them. Not long after she stuck her fingers inside her and started fingering herself. When she did this, she put her hand behind my head and guided me to her breast, moving her fingers in my hair as I kissed and licked her nipple.
After a bit of watching this, she pulled her fingers out and offered them to me, which surprised me, due to her reaction of me licking her cum soaked shorts. While I was sucking the sticky wetness off her fingers, she grabbed my hand and moved it between her thighs, so I slipped two fingers of my own into her and began to massage her gspot like I know how.
It took only a few short minutes for her pussy to start pulsing around my fingers and her cum to start seeping out of her and onto those same fingers. She tensed up pretty hard and her stomach was tightening and relaxing as her orgasms coursed through her. It was pretty intense to watch, and she looked so beautiful as she climaxed. She fell back onto the mass of pillows and my sticky, cum coated fingers slipped out of her.
Unable to resist, I immediately put my own fingers into my mouth and thoroughly cleaned her cum off of them. After that I let her body recover, as she couldn't really move much for awhile, and then I helped her into her room, and into her bed, completely naked this time. I imagine Steven woke up to a nice surprise this morning.