My First (time) Taboo

Ok, this is where my life got more complicated, but it also got so much more interesting and exciting. Still I'd read the first three chapters or you might get lost.

After a wonderful weekend with my mother, I was back at school and happier than ever. Denise and I were becoming very close and I was also really enjoying time with my roommate Alley. I spent more time with Denise than I did my own roommate, but what time I did spend with Alley was very fun.

I was more daring with Denise and it was mostly due to some of Alley's comments. When she found out I was friends with Denise, Alley suggested that Denise might be a lesbian. She pointed out that she never talks to any boys and she dresses like a guy. Alley and I of course had guys in our room all the time. Alley is gorgeous and a bit of a flirt, plus the boys all seem to like me too. And for the record, no I am not interested in boys at all so please no more e-mails about wanting to be my "friend," because you like girls just like I do and that gives us something in common. I don't mind talking to boys or hanging out with boys, I just don't want anything more. Anyway, I digress.

So since Alley said those things I took note of it and realized that Denise and I had never discussed boys at all. Still I was afraid to just come out and ask her, but I did start to flirt with her sort of. A few times over those two weeks I managed to get my hands on her shoulders and give her a massage while we studied together. The first time was awkward, but when she realized how nice it felt she didn't stop me, and the second time she just relaxed right away, but her roommate came in and interrupted us so that sucked.

So two weeks after I had made love to my mom (like I said if you haven't been reading the other stories I'm sure you're lost about now), I went home again. She somewhat insisted and told me she had a surprise for me. I assumed it would be a wonderful weekend with just the two of us, but when I got home late on Friday she surprised me alright. She and Anna, my mom's girlfriend, had set me up on a blind date with a friend of Anna's. It was a double date no less. So here I am going out with someone I've never met and the whole time wishing I was home with my mom in bed, but somewhat angry with her for setting me up in the first place.

The girl's name was Sydney. She's pretty. She has blonde hair and she's not pale, but she just seemed sort of washed out to me, like if she didn't have on make-up she'd just not have great color. But she had a nice smile, pretty eyes, and a nice body. Sydney's twenty-four years old, and myself being only 19 it was just sort of uncomfortable for me at first as we had little in common, but I still ended up having a really good time that night.

Now sparks didn't exactly fly, but after dinner and a movie we all went back to my mom's to hang out. Now no way in hell, was I going to have sex with a complete stranger, but my mom actually asked me if I thought I wanted to. I couldn't figure out what was going on with her, but I guess she was just trying to make me happy. I did kiss Sydney that night. She was a good kisser and I could tell she was really into me, but by midnight they were both gone and it was just my mom and I alone.

We talked for a while mostly about Sydney and a little about Denise, and then I just sat on her lap and we ended up kissing. Earlier in the night I had grabbed her butt, when Anna and Sydney weren't looking, and I sat by her in the restaurant and put my hand on her leg a few times. Finally we could get down to business. She admitted to me that she was horny for me all night as well.

We didn't kiss long before we began to undress one another, and soon we were headed upstairs to her room. Soon we were underneath the covers naked and I was kissing her like I hadn't seen her in months. I have no idea why I was so horny for her, but I was so energized that night. We just touched each other instead of the usual, but I bet I spent a half an hour on her breasts.

She kept saying things to me like, "Would you like to do this to Sydney," and "Don't you think Sydney was pretty," and such stuff, but I mostly just ignored her or was like, "Yeah." I was starting to think my mom had the hots for Sydney.

The next morning when I woke up in her bed everything just got weird. I laid there thinking, "Did I just go out on a date with my mom." It had seemed that way. She obviously was trying to get me interested in someone else and yet the two of us had still ended up together. I started realizing that it was me who had started all this and I was also the one who was always the instigator. I felt bad. It felt all wrong. I bet I laid there for an hour just thinking about everything before she woke up, but as soon as she did she rolled over and started kissing me. I was so confused.

As soon as I felt her enormous breasts rubbing against me I just felt all weak and dizzy. It was like there was this cloud I was seeing the world through. I can't explain it any better than that. She was quickly on top of me and I remember squeezing her ass as she kissed me. I kept pulling on her cheeks and bringing my hands lower and lower until they were teasing her asshole. She seemed to like it a lot. Then she asked me if I wanted to go in the shower with her again. So we did.

I licked her ass again. I can't believe I do that, but there's just something about my mom's ass that gets me going. I know that sounds so strange, but it gets me and her so hot. We both made each other orgasm before we left the shower.

Later that day my mom invited Anna and Sydney over for lunch. We had fun again, but I didn't even kiss Sydney that time, though I did kiss my mom's neck and grab her boobs from behind when we were alone in the kitchen again. She seemed more scared this time than excited, but it got me really horny.

That was pretty much the end of that weekend. I spent the night on Saturday, but my mom and I didn't do anything. We just sat around and talked and fell asleep watching a movie in the living room. The next morning I went back fairly early as I had work to do for school.

Now Sunday is when my life got most interesting. First off, I had this very strange conversation with my roommate Alley, who explained to me how she kissed one of her friends, a girl named Nikki who by the way I think is a real slut, at a party because they were both drunk and a bunch of guys talked them into it. She admitted she loved the attention, but she was worried cause I guess some guys filmed it on their phones. I didn't feel sorry for her at all, but I did get a little aroused by it.

I wouldn't call Nikki pretty, but she's cute. She's like one of the girls I used to cheer with that were always made up real good, and had nice bodies, but the guys just liked them because they were easy. Well that was Nikki. But Nikki does have huge boobs. I'd say she's about my size, and I have to admit I do stare at them when she comes over.

Picturing her and Alley kissing got me a little wet. I asked Alley if she ever did anything else with a girl and she told me she hadn't. Then she asked me and I just froze. I wanted to say yes, but a bigger part of me wanted to say no, but instead I just said nothing and smiled. She didn't freak out, but she was acting like she couldn't believe little miss perfect would ever do anything like that. She never called me that, but she treated me that way.

So I just told her, I hadn't, but I'd thought about seeing what it was like to have sex with a girl. I thought her mouth would fall to the floor, but she didn't look pissed or nauseated so I wasn't too scared. She flat out said she could never do that, but then later she said she'd have to get really drunk. I'm not sure why, but suddenly I wanted to test her theory.

Then to add another great thing that happened that day. Later in the evening when I was studying with Denise in her room, she asked me to massage her shoulders. Of course I said yes and I even suggested that she lay on her bed. She was wearing a T-shirt and when she lay down her breasts were smashed out on both sides and I thought I was going to go crazy. I wanted to find an excuse to touch them, but I just couldn't do it. But I did straddle her and my pussy was right against the bottom of her ass. At that point in my life it was the sexiest thing I had ever done short of massaging my mom's breasts with oil. I so wish we had been naked.

I made sure to mention what Alley had done the night before, just to get a reaction from Denise, but she didn't seem to like Alley and she just said it didn't surprise her or something.

The next four weeks were pretty uneventful. I went home every other weekend. I went out with Sydney on the weekends I went home, and I hung out with Denise on the other weekends. Nothing of course happened with Alley and she didn't seem to treat me any different either after my confession. So that was good. I didn't have sex with my mom either since I was actually starting to look at Sydney as a serious possible relationship and probably a lot healthier one, definitely a more acceptable one. I made out pretty serious with Sydney on our fourth date, and she actually grabbed my boobs. It seemed so weird. She was the first girl who had ever touched me like that. I mean my mom did, but Sydney just seemed different. I'm not saying I didn't like it, but it was just so very weird.

I was actually pleasantly surprised when I first put my hands on Sydney's breasts. They were full, round breasts and her nipples got really big. I sucked her chest that night and she sucked mine too. She told me I had the most amazing breasts she'd ever seen. I had to wonder just how many she'd seen, plus what was I supposed to say to her after that? So I told her hers were wonderful, but I felt stupid after I did. We kissed a lot and she ended up putting her hands down my pants and rubbing me, but I didn't orgasm. I just couldn't, but I'm not sure she knew if I did or didn't.

I felt like I was cheating on Denise, which was stupid because we were just friends, and yet I wasn't in love with Sydney. I didn't even offer to touch her, but when she took her pants off I did eat her out. She seemed to like it, but now I felt even worse not because I didn't enjoy what we had done (though honestly it wasn't that great), but because now I didn't think I wanted to date her anymore, and how do you break up with someone after what we just did? I felt like a horrible person. I think if I didn't have feelings for Denise I think I would have possibly had something with Sydney, but I couldn't help how I felt. Still not knowing how Denise felt and wanting to make my mom happy I lead Sydney on. I'm telling you all now it was a huge mistake, but one I can never take back. Hopefully none of you make the same mistake as I did.

The next morning I told her I had feelings for someone else. It didn't go horribly, but she thought I had feelings for Anna. She said she noticed I always looked at her weird when she and my mom showed affection to one another. I couldn't exactly tell her the truth, but I certainly told her it wasn't Anna. I'm not sure if she believed me or not.

She left with Anna not to long after our talk. Then I told my mom and she seemed disappointed, but more for me than with me. She kept asking me if I was going to confront Denise, but I couldn't answer her. I still didn't know what I wanted to do. My live was very complicated.

Anna and my mom went out that Saturday. I just stayed home alone. I think I had school work to do or something or maybe I was just tired. When they came home Anna acted a little differently around me and I had the feeling that Sydney told her she thought I liked her. I had always used to flirt with her, so I could totally see why she'd think that. So when she gets me alone she asks me. Of course I denied it. I told her I would never hurt my mom. Then I left the room before she could even say anything else and I went and told my mom. Then my mom asks me if I like Anna. I was like what is going on here. It wasn't like she was mad at me, more concerned, but I told her I wasn't interested in Anna.

So I went to my room and jumped on my computer. I was up there for an hour before I came back down stairs and I heard my mom and Anna making out in the living room. They were going at it big time and I just watched them. I felt dirty at first and then actually a little jealous. Anna was touching my mom's breasts. The breasts that I loved touching and sucking. Talk about crazy emotions.

I did see Anna's breasts and they are very nice, also about my size maybe a little smaller. They looked a little perkier than Sydney's, and I'll admit that I did fantasize about walking in their and joining them, but I didn't. Instead I went up to my mom's room and got her strap-on.

Ok girls let me teach you a trick. Strap it really tight to your bedpost (this is not easy, but it's worth it) and then get on all fours and back into it. That's what I did that night. I just pictured my mom doing me from behind and I pinched my nipples one at a time and pictured her hands on them. I fucked myself crazy, and then rubbed my clit until I climaxed.

I was done when my mom came in to say good night to me, but it was still strapped to the bed and I was naked. She looked so horny for me, but Anna was in her room waiting for her. I sucked her breasts, her huge soft amazing breasts, and we kissed, and then I told her to picture me while she had sex with Anna. She told me she would and then she kissed me before she left.

All for now, but I'll tell you more about Denise and I next. I'm really enjoying telling people about myself. It's kind of therapeutic. And thanks again for all your replies.