My History (8th In A Series)

I have no news to report at the moment. My life is very stable and calm, thank goodness, so as promised, I'll step back into my crazy past and post the story of how I wound up in a hotel room with my best friend, the daughter of the woman I was dating, and her best friend.



Displayed in the post "My History (2nd In A Series)" are the details of the torrid relationship between me and "Sarah," the woman I screwed on the side while dating "Karen." I mention some of the drama I went through with Sarah's 22-year-old daughter, "Elaine." If Sarah and I would have never become a serious couple, which we did only after I came begging to her for a shoulder to cry on after Karen fucked me over, I'm 100% positive that Elaine and I would have eventually hooked up. Not only did we have a lot of sexual energy between us, but the first time I ever saw her was when she came to her mom's house while Sarah was talking to me on her webcam, and very soon after, there they both were flashing me and pulling their pants down and bending over for me. (My best friend at the time, "Ronnie," happened to be at my place when this happened, and he was even more crazy for white pussy than I was, so as you will read later, seeing this display had an effect on him too.) For a long time I really thought that Elaine and I would fuck, and I wouldn't have been surprised, as kinky as Sarah was, if we one day had a threesome. It didn't hurt that Elaine was very fat and egg-shaped and, despite being engaged, didn't seem to have a high opinion of her desirability, which has always been a common mindset of the women who had relations with me. Elaine and her hot friend, "Talia," came up from Springfield, IL, with a male friend one weekend in 2004 just to hang out in the big city, and we did a lot of flirting in between everyone trying to convince me that Sarah would hurt me someday and she wasn't a great human being, which I didn't want to believe but would turn out to be true. Elaine and Talia even flashed me and their friend while we hung out on the beach. She pecked me goodbye on the lips as she dropped me back off at my apartment, and I got the feeling that if she were not with two other people hoping to go back home, she may have stayed with me a little longer that evening.



A little about Talia: I believe at the time she was 25, she was married, and she had four children, and I've since heard that she had a 5th child. I don't know how she got to the mental state that she did, but she basically did whatever floated into her pretty little head, whether that was fucking other guys, fucking other girls, or whatever. She and Elaine were lovers. And she was just about the nicest woman I ever met, too. She just seemed very dissatisfied with her life. She claimed that her marriage was an "open relationship," but I've always believed that no one really goes into marriage intending to ignore the vows right off the bat. If it turns out, however, that neither you or your partner can't survive without lovers on the side, then it becomes convenient to say that, well, "It's just an open relationship and we don't have boundaries." What the hell do you call marriage? That's a large boundary I believe, but as it's well documented, half of the couples that try it discover that they're not cut out for it with each other. Anyway, Talia was of mixed racial heritage, so she had exotic facial features, long wavy black hair, and large round tits with damn near the biggest areolas I've ever seen, so big that Sarah and Elaine showed me a picture of her topless the first time I visited Springfield just to marvel at them. She wasn't obese, but she had Cesarean sections for all of her child deliveries, so she had no abdominal muscle definition at all, just a spare tire of flab. She was still gorgeous as far as I was concerned, but I never thought I'd get a shot at her because her social calendar was so full, and because she seemed way out of my league.



Until that wild, insane summer night.



It's Saturday, July 24, 2004. Sarah's not coming up to Chicago that weekend. Two weeks prior, I fucked The Co-Worker Who Shall Remain Nameless for the first time, proving that I have no morals, I wasn't above cheating on Sarah, and that I was up for anything. But The Co-Worker and I weren't social buddies, so we weren't going to hang out that weekend. I had no plans. In between my loads of laundry, Elaine called that morning and informed me that she and Talia were going to drive up to Chicago that day and wanted to hang out like we did a couple of months prior when they came up with their male friend. But this time, she said, the male friend wouldn't be there. My mind raced with unscrupulous thoughts of what kind of stuff we three could get into. I said that I was looking forward to seeing them and hung up. Not very long after, Ronnie called and asked if I would have any interest in attending the bachelor party of a guy who was in a fantasy football league that Ronnie and I participated in. He said that the guy was hiring women from the same agency that sent us two girls for the football draft in 2003, and for $10 those girls allowed anyone to spray whipped cream on their tits or pussy and lick it off. I ate a LOT of whipped cream that night. So there was no doubt that I would be up for this event, but I asked Ronnie a question: Did he think the guy would mind if I brought two women to the party who both loved slutty women as much as the men did? When I told Ronnie that Elaine and her friend were coming to Chicago that night and they would probably love attending a party where whipped cream were being licked off of women's body parts, he had the same thoughts that I did--holy shit, what a hot, sexy night it would be if we popped in to an anything-goes bachelor party with two bisexual chicks. I called Elaine back and asked if they would be interested, and she was even hotter for the idea than me and Ronnie. It was fucking awn.



My camera was hanging from my neck when Elaine and Talia arrived at my apartment that evening. They were actually filling up the tank at the gas station a block away when they called, and I was so pumped for this night that I came to the station on foot before they could come pick me up. Ronnie had given me generic directions to the golf course where he was working until sundown, and we were to meet him there and then go to the party. But I wound up having to call Ronnie a couple of times to figure out where the hell we were going. On the way, while sitting in Elaine's back seat, I expressed in interest in seeing the tits that the ladies had flashed me the last time they were in Chicago, and somehow, my hands wound up inside both women's bras rubbing a nipple each as Elaine tried to drive somewhere she wasn't familiar. Hey, I actually asked (like a nerd) if they had a problem with me groping them, and they both said they liked it. When we finally made it, we had to walk through a gangway to get to the clubhouse area where he was, and then we spotted him. He had on his usual geekwear, tan shorts and an ugly shirt, but that didn't stop Elaine from being very friendly with him, and of course he was thrilled to meet a girl whose naughty bits he had seen on webcam already. Not wanting to show up to this shindig too early, we hung out on the patio of the clubhouse for about an hour shooting the shit as the sky turned black, then decided to have dinner. Ronnie convinced the girls to leave their car at the course and get in his back seat, and after dinner we'd come back to get their car and head to the bachelor party. It was such a sexually charged atmosphere that during the drive to the restaurant, the girls mentioned taking off their tops, Ronnie and I dared them, and in the blink of an eye, I turned from my passenger's seat to see both of them sitting there with their shirts and bras completely off, with these blank looks as if they didn't think there was anything strange at all about it. Ronnie could barely drive. I was just shocked. They sat like that for a good two or three minutes until Ronnie saw flashing lights and begged them to cover up or risk getting in trouble with the cops. (The lights were cops, but they were after someone else.)



After dinner, Elaine and I got into Ronnie's back seat while Talia sat up front. We didn't make out, but I did say "Now, where was I?" as I put my hand down her shirt again and she rubbed my boner through my jeans. We got back to Elaine's car, and I rode with the girls, giving them tit massages again as Elaine followed behind Ronnie to the bachelor party. It was past 10P when we arrived, and the strippers were not there yet. The guys inside were a little restless to say the least, and definitely a little mean: When Elaine offered herself and Talia as a warm-up act, the guy in charge of the party looked them up and down, sniffed and actually said out loud, "I don't think so." Elaine and Talia stepped outside right after that. Ronnie and I didn't know what to do, so we sat there for a little while muttering under our breath at the asshole who said such a cruel thing, then I stepped out to check on the girls. Elaine was smoking and cussing the guy out under her breath too, which was a normal reaction. But Talia was actually in tears. It turned out that she was very sensitive about her looks since the babies and the weight gain. I tried to console Talia, but she wasn't in a mood to be consoled. Elaine suggested that we get out of here since she really didn't want to be in the same building as that guy anymore, and that sounded like a great idea. But where to go at midnight on a Saturday? I went back in to talk to Ronnie about what our next move should be, and it dawned on me that with two vulnerable, horny, wild women, it shouldn't be too hard to convince them to get a room just to "hang out," and whatever happened from there happened. I was literally right in the midst of trying to tell Ronnie that they probably would be up for it when Elaine came back in the building and said they were going home unless we had other ideas. And then it got weird. When Ronnie brought up getting a room, Elaine said that sounded like a plan, and the woman I had flirted with and smooched and groped for several months playfully grabbed my best friend's junk as she walked out the door to tell Talia what the deal was. He looked at me stunned with his eyes bugged out as his manhood got hard right in front of me, and I'm thinking, GOOD GRAVY that was not something I ever needed to see. "Told you they'd be down for it!" I said, trying my damnedest to purge that image from my mind.



I didn't know how to feel at this point. Yes, Ronnie and I were in his car driving to the south suburbs to find a hotel with vacancy, and yes, two women seemingly willing to fuck one or both of us were following behind. I should have been thrilled, but I had conflicting feelings. I wasn't entirely comfortable with Elaine indicating that she would be willing to screw Ronnie mere hours after meeting him. I kinda felt like I had dibs on her with all the flirting we had done. I don't know if I wanted him to have Talia and I would take Elaine, or if I just wanted Elaine first and he could have my sloppy seconds, or if I thought I should be the one to fuck them both since I was the one they came to Chicago to have fun with originally. And yes, cheating on Sarah was in my mind as well. I felt guilty about that, but I was so spiritually empty at that time in my life that I wanted to fill my life with as much flesh as possible, thinking that was the way to feeling better about myself. Ronnie was so immature that what he had on his mind was calling his mother to tell her he'd be having a late night, and then it got weirder--he informed me that he had to go back to the city go get his mom the Sunday Sun-Times newspaper that is sold on Saturday nights, then he had to take it home to her before we found a room. I sat in Elaine's car outside Ronnie's house laughing at this turn of events, but there was no mutual tit-rubbing this time because Talia was still upset over the happenings at the bachelor party. I continued to try to console her and tell her that she was still hot, but she really didn't seem like she would be much fun the rest of the night. I think Elaine asked her at one point if she wanted to go home, but she said no. She probably didn't want to seem like a buzzkill. Eventually Ronnie came out of his house, I got back into his ride, we drove about twenty minutes south to a bunching of hotels, and after striking out on the first four or five attempts, we hit pay dirt. I got out and checked the availabilities of the rooms while Ronnie and the girls parked, and I made a decision that made the events that unfolded a little easier to digest than they may have been: I got two rooms instead of one. I also grabbed my camera. Dammit, I came out that night to get some wild action caught on film, and that's just what I was gonna do.



We all made our way up to one of the rooms with no plans as to what was going to happen. It was around 1:30A. Elaine, Talia, and I sat on the king-sized bed. Ronnie sat in a chair nearby. We nervously chatted for a few minutes. I pulled the nerdiest move of all time by turning on the TV because I didn't know what else to do. I think Ronnie and I actually started checking baseball scores. Finally, FINALLY, Elaine said out loud, "Well, you guys didn't pay for these rooms to sit here and talk," and with that, she shoved Talia on her back, took off her top and bra, and sucked her breasts, then she jumped off the bed, pulled her jeans and panties off, and started eating her out. Talia responded the last way I would have predicted--she grabbed a pillow and covered her head as if she were experiencing something awful. I responded by taking three pictures, two of Talia's awesome tits (although her covering her head with a pillow takes away from the beauty of those pics) and one of Elaine on her knees eating Talia's pussy. In the background of that last pic one can see Ronnie starting to put his hands on Elaine, since she happened to be kneeling next to the chair he was sitting in. Things moved fast from there--Elaine responded to Ronnie putting his hands on her by taking him to the upper part of the bed, pulling off his pants, and giving him the sloppiest-sounding blow job I've heard this side of Gianna Michaels. I took off the camera and quickly got over any feelings of envy having to hear Elaine sucking off my friend by taking over where she left off eating out Talia. It dawned on me that, hey, Talia didn't completely freak out when I tasted her, and after a few minutes, I took the pillow off her face, said, "Do you wanna go to the other room?," and pulled her up by the hand. She took forever gathering her clothes to make the walk across the hall to the other room, but eventually she got dressed. Then, while I was getting more and more geeked at the thought of having sex with Talia, who really is a very attractive, sweet woman, she stopped Elaine in mid-suck to ask her to join us, to which Elaine responded, "I'll be there in a few minutes." So I'm thinking, wow, I'm about to nail Talia, and then Elaine is coming later to show me those oral skills she's currently displaying on Ronnie? What a night!

We had not been in that other hotel room for more than five seconds before Talia turned to me with this sorrowful look on her face and said to me, "I'm sorry Dre, I'm not in the mood." I had never been more in the mood than at that moment, so I spent the next 45 minutes or so trying to cajole Talia out of the clothes that she just put back on. Somewhere along the way I got her top off, and I remember kissing her and sucking her tits, and my shirt was off as well, but I wasn't going to take my pants off until I got her legs back open again. But that never happened. No matter how hard I tried, no matter how much I begged, Talia was not interested in fucking me. She called Elaine a couple of times, but Elaine was a little preoccupied and assured her that she would be over once she was done. Then at one point she got this sorrowful look on her face again and said, "You're going to fuck me, aren't you?" This indicated to me that she expected me to take what I wanted instead of begging all night, and if I intended to rape her she wanted it to be over with. I instantly lost my boner and stopped trying to fuck Talia. I felt like such a turd. From there, we actually talked for about three hours. She told me about her emotional problems, that she was on anti-depressant medication, and that she didn't have high self-esteem, and I wound up spending most of that conversation trying to tell her how attractive she was and how she seemed to be a good person (despite her "open marriage"). I gave her so many compliments that at one point she smiled, touched my cheek, and said, "Wow, you're really good for my ego!" I choose to hold on to that as the highlight of my night. I don't know if I had any lasting effect on Talia, but I got the feeling that not a lot of people had spent all night making her feel good emotionally. Physically, sure, but not emotionally.

Elaine never came over to my hotel room. She would explain in an e-mail that she felt guilty about potentially fucking her mother's boyfriend, making her by far the most mature and adult person in that entire situation. Talia called her at about 5A and expressed the need to leave right now in order to be back home ASAP. I think she started to become worried about her husband, who didn't know she was pulling an all-nighter. When I walked into Ronnie and Elaine's room after the girls had left to go to the car, Ronnie was still there, and all he could say was, "Man. The room still smells like sex." And he was right. There was a sickening mix of cum scent in the air that I know wouldn't have affected me at all if I had been able to screw Talia and create my own funky-smelling suite. But I'm willing to bet that not a lot of you know what it feels like to stand in a room where people have been having wild monkey sex and it smells like it, and you thought you would get some of that wild monkey sex all night long, and you got bupkus. It don't feel good. Ronnie kept asking me what was wrong because he could sense that I was not in a good mood, but I couldn't tell him at that point. I just gave him the $80 for my room, which I owed him because he put the rooms on his credit card, and I slinked into the passenger's seat of his car. I then had to watch him and Elaine kiss goodbye outside, and I mean a long kiss goodbye, complete with blow-off wave at me before she got into her car and drove away. I never saw either Elaine or Talia again. Ronnie was good enough to drive me home, which was an hour north. As the sun came up, I did tell him during the drive that Talia and I didn't have sex, and he basically said nothing the rest of the trip. I think he was completely speechless, and so was I.

I'm reminded of this story occasionally when I spend time with "Jacob" and a friend of his. This friend was there at Jacob's house years ago during a New Year's Eve when Jacob and I were playing football on his PlayStation. One game came to an end when I got a touchdown with no time on the clock to pull within one point. An extra point would have forced overtime, but this friend and others implored me to go for a two-point conversion and the win, so I did, and Jacob made a spectacular play to stop me at the one-inch line. The friend immediately screamed, "Why did you do that, you idiot?" I said, "You told me to!," and he said, "I'm drunk! What are you listening to me for??" It's a funny story, and the friend branded me with the nickname Go-For-2 afterwards. Well, I told the long story of this wild night with Ronnie and Elaine and Talia to this friend a couple of years ago, and after I finally got to the conclusion, he deadpans, "So I guess now we can call you 0-for-2." That's one of the greatest one-liners I've ever heard. It was accurate, and it was delivered so straight that I never saw it coming. It helped me get a chuckle out of the sad fact that I had my hands on not one but two horny women who were probably willing to have sex with me at some point during that evening, and I wasn't good enough to pull either one. In all my adventures, there are no occasions more pathetic than this one.