Chicago, Chicago, That Toddlin’ Town
Chapter 1
Here I was, 33, single, and just recently transferred to Chicago. I was sent here to get this upstart IT company on its feet. We recently acquired it and they need me to make sure it got up and running, our way, and to make a profit. And now 3 years later, I’m loving my life.
I’m Blake, and as I said, I am 33, single, 6’, 190 lbs, with short blond hair. I generally work out at least 3 times a week, so I am in good shape. I’ve been told I am good looking, and judging from the fact that I can land a date pretty easily, I guess that is true. I also was blessed with an above average cock. Almost 9 inches long, and 5 inches around. Not real fat, but not real skinny either. Never had a woman complain, at least not to my face.
I grew up in Central Ohio. My father and mother divorced when I was young, and mom moved away, leaving me with dad. Dad remarried when I was just starting to come into my puberty. His wife, my stepmom, Sophie was a little younger than my dad, and always treated me good. Sophie had a cousin, who she was quite close with, Nancy. Nancy was divorced as well, but had a farm, that was, at one time, was her parents. Nancy had a daughter, Karen, who was my age.
Since we used to go over to Nancy’s a great deal, Karen and I became friends. We used to hang around all the time, and explore the farm and surrounding areas. Or, I would help her with chores. As time went on, we became close, to the point where we would discuss anything, even sex and dating.
Now Karen was average looking, not stunning. She was 5’ 8, by the time we graduated, but thin. I mean she may have weighed 110, soaking wet, had a small ass, and small up in the chest department. Was I attracted to her? In some ways, yes, but I did prefer girls then, with big boobs. Now her mom was a little bit shorter, 5’6, both had blond hair, but her mom sported a good 36D chest and had a killer ass too. I caught dad checking her out a few times.
I remember one summer day, just before our senior years. We’d just got done fixing a fence out in the field and were coming up by the house. We were just outside her mom’s bedroom window, when we heard,
“Oh God Damn Sam. Fuck Meeeeeeeeee”
We stood there and listened for a good 5 minutes. Luckily for me, I was wearing jeans, or Karen would have seen my hard on I was sporting, if I was wearing my normal basketball shorts. I could tell Karen was getting a bit worked up too, because her breathing had changed. Karen finally said, whispering, come on, let’s get out of here. Now Sam was a hired hand around the farm. We kind of had a feeling Nancy had a thing for him, but this confirmed it.
Now don’t get me wrong, Karen and I, over the years, were first for each other in some things. Like our first kiss, and seeing each other naked, and even oral sex. We never went the whole way, and to this day, I don’t know why. We also did stupid teen things like drink, smoke weed, and tried coke a few times. When we did date others, we told each other how it was between us, our significant others. We both lost our cherry’s in our junior year. Then at the end of our senior year, we escorted each other to our prom’s. Sometimes it felt like we were more like sister and brother, than friends who could, if we wanted to, have sex. But we were fine with it.
Towards the end of our summer, after graduation, we headed off in separate directions for college. Karen had always wanted to be an interior designer, and carried a 4.0 gpa all through high school. She landed a full scholarship at Columbia College in Chicago, which was a big in Interior Design. I went on to Ohio State, and got my Degrees in Business Admin and a minor in IT programming. I even earned a Master in Business, while working for my present company, which they paid for.
During our whole time away from each other, we still stayed in touch, and chatted frequently by phone or emails. After graduation, I lived in with a girl that I had been dating. We both lived outside of Cincinnati, which is where my company’s headquarters is at. She was in banking investments.
It was good for a while, but she wanted to get married, and being I was only 24 at the time, I did not want that yet. So after almost a year, we split up. From that point on, I tried hard, not to get serious with anyone. Just date, and have a fuck buddy. Trust me, there is plenty out there just up for that type of relationship. I dated all types too. Plump, skinny, white, Asian, and even a black lady who was about 10 years older than me. She was awesome in bed. She had a thing for white guys, and if he was packing, all the better.
Karen too, dated on and off, and even lived with a guy while still in school. But he cheated on her and they broke up. A few years later, she was dating a guy, but then found out he was married, so that soured her on guys for a bit.
Then about 5 years ago, she floored me when she said she was dating again, but this time it was another woman. I kind of had a feeling she may go both ways, because when she was in college, her roommate and her were thick as thieves, and did almost everything together. As she later told me, how could they not try things. 3 years living in the same dorm room. Seeing each other naked all the time, and becoming close, it just happened and she loved it.
After a year of dating, and living separate, they moved in together. Both Nancy and Sophie were supportive of this relationship. I know that both of the ladies wanted Karen and I too become a couple, but that was never to be back then. All I knew about Chrissy, was that she was our age, and also worked in the same company that Karen worked for, and that she was African-American. I was happy for Karen, I truly was. I’ll admit, I’d love to witness those 2 going at it.
Chapter 2
Two weeks before I was to move, I called Karen to let her know I would be coming to Chicago, and my intentions there. I thought my eardrum was going to burst when she let out a loud shriek, over the phone. She asked where I was going to stay, and I told her a hotel for the time being. She told me “Bullshit you are”. She said I was going to stay at her condo, until I found my own place, no matter how long it took. I relented and agreed to her demands. I did promise to pay her what I would pay a hotel, but she would have to make out a bill so I could expense it.
I arrived in the evening and Karen was at the airport to greet me. When she saw me, she ran up and wrapped her arms around my neck and kissed me hard, right on the lips. She was still tall, and skinny, but her legs had more definition to them now, In fact, they looked great, since she was wearing shorts that barely covered her ass. Even her ass looked a bit bigger than I remembered. But, she still had small breasts, maybe B cup at best. Her hair was still blond, but cut shorter now. It used to be shoulder length, but now was just above her neckline in one of those bob cuts
We talked and talked the whole way back to her place, which was a good half an hour away. My new job was 20 minutes from her place, she explained. She said Chrissy was dying to meet me as well. I wasn’t sure how I would be received by her, seeing Karen and I had a very long history together. I even spoke my concerns to Karen, who then laughed.
“Blake, Sweetie. She’s cool. She knows all about us and how close we are. Anyways, we may be lovers and all, but we’re Bi, not lesbians. Plus, officially we, you and I, were never lovers in the true sense. I wish now that we had been. But I am still happy you are in my life and we do love one another, and if I love you, she’ll love you too, eventually.”
I just smiled to myself then thought back to how close we came on a few occasions to going “all the way” Lord knows I wanted too, but never sensed that she did, so I never pushed that.
“Okay” I said…. “I just don’t want to put any strain on your relationship with her.”
Karen laughed. “Trust me Honey, you won’t put no strain on what we have. Plus, if she ever sees that man meat of yours, I’ll have to tie her down, so she doesn’t come into your room and rape you.” then chuckled more.
Once at her condo, we found Chrissy in the kitchen fixing dinner. My jaw had to have hit the floor when I was her. She was as tall as Karen, wearing these bright blue short shorts, with PINK written on the ass. She had only a t-shirt on, but her legs were stunning. A milk chocolate brown complexion and, like Karen, short brown hair bob cut. Her breasts were a little bigger than Karen’s too, but her ass was to die for. God, I thought, what I’d give to see these two making love.
She stopped what she was doing when Karen introduced us. She came right up and gave me a hug and a kiss. “Friendly”, I thought. I just stared after she turned and went back to whatever she was doing by the sink. I mean, what an awesome ass she has. She had to know I was looking at it too. I don’t believe she had any undies on either, for the material was sucked right up into her crack. Ok. I was jealous that Karen got to enjoy that.
Dinner was great and we all had a good time talking. After dinner we retired to the living room and just talked. I explained what my job was going to entail and some of the hours I would have to put in. They in turn, told me about their jobs and some of the clients they had. Both girls did complain at how some of the richer men thought that they should bed them, just because they were rich and had given their company the contracts.
Karen laughed when she said, “Yeah. They back off once we tell them we are lesbians. They don’t need to know that, if it is the right guy, we’d swing both ways.”
Chrissy chimed in, “Yeah. He better respect us and be hung like a porn star and knows how to use it and last all night.” then smiled at me and winked.
Now granted, their lips were loosened some by the bottle of wine they were consuming. But if I didn’t know better, I’d say that Chrissy was flirting with me. I couldn’t help but notice that Karen was wiggling around a lot, like she was horny. So after another half an hour of just shooting the shit, I said I was tired and made my way to the bedroom they set me up in. They too, went off to bed.
I just lay there thinking of both of them. Just being with Karen brought back great memories for me. I had always found her attractive, and when we did play around, it was some of the best I ever had, even if it was only oral. Back then, I wanted to make love with her, but always was afraid it would ruin our friendship, and I never wanted that to happen.
Then I thought of Chrissy. “Fuck”, I thought. I bet she is a spitfire in bed. I tried to form a mental picture of her naked. Dark nipples perched on to firm breasts, and lovely shaved pussy, just begging for a tongue or dick to make it feel better, oh yes, that wonderful ass of hers too. I wondered too, if Karen shaved her pussy now, like most of the women do this day and age. The girl I used to live with got me to shave. She said it looked sexy and liked not having hair in her mouth during a blow job.
My cock was rock hard and I had to stroke it. As I was, I could hear muffled moans coming from down the hall. They were getting it on. That just spurred me on even more, as I stroked myself to a huge orgasm. It landed on my chest and belly and all over my hand. To bad it wasn’t in one of them. It had been a couple of months now that I was with a woman. Then I heard Chrissy moan out loudly, and Karen shush her, then both giggled. After that I was asleep.
Chapter 3
It was now a week and half later. Things were going good. I had been putting in 10 hour days and finally was getting a grip on things at work. Some changes needed to be made and after conferring with the home office, they pretty much gave me carte blanche to do what I thought necessary, up too, trimming the labor involved.
On the home front, I think we were all getting comfortable with each other. I tried to stay out of their way and not be a hindrance to them. I had Karen go online and find billing invoices and she made one out for 250 a week in rental. The home office was allowing me 500 a week for living expenses. But that was for only 6 weeks. When that money came through, I was going to pay her the full amount. Of course she said bullshit, but I finally talked her into it. She said she would put it into the Fun Fund, that they had. Lord knows what that is used for, but I would later find out.
Also, we were working out a bathroom schedule. The condo had only one bath with a shower, and a half bath downstairs. So I made sure I was up before them and took care of business, like peeing and such and a shower. The girls were happy about that, since they pretty much hog the bathroom in the morning. And, after the first week, they were cool with just walking around in their undies and bras with me around. I surely didn’t mind. Karen was also giving me a kiss every morning before I left for work and one every night before bed. It wasn’t a cheek kiss, it was one right on the lips too. Talk about sending mixed messages.
Then Chrissy started noticing Karen’s kisses and said, “Well shit, don’t I get some sugar too Blake?” So I went right up to her and kissed her tenderly on the lips. From that moment on, I was receiving kisses from the both of them.
I awoke that Thursday with a half hard on. Noting that I am usually up a good half hour before them I just went to the bathroom, wearing only my silk boxers. As I was approaching the bathroom door, it suddenly opened and out came Chrissy. All she had on was this peach, at least I think it was peach judging from the bathroom light, almost see-through throw wrap on. We stood and stared a moment at each other. My eyes went to her breasts and her dark nipples so easily seen and her eyes went to my crotch.
Then in a low, totally seductive voice, she said, “Like what you see vanilla? Cuz I sure do” and then kissed me on the cheek. I’m sure my face was beat red now. She had started calling me Vanilla the other night because we had been watching some movie together. She was in the middle of Karen and I, on the couch and said, “Damn, I feel like a reverse Oreo. Two Vanilla’s on the outside and this yummy chocolate on the inside.”
I just went ahead and showered then and got ready for work. As I was leaving, I yelled up to them, since they weren’t done getting ready, not to forget that I was taking them to dinner that night. I wanted to get out of there before it got a little weird, at least for me. So far nothing wigged these two out. Hell, they must make love 5 or 6 times a week too.
Later that evening, I was up in my room changing to go out to eat. The girls just got home too. There was a knock on my door, and before I could say wait, since all I was wearing was my boxers, the door opens and in walked Karen.
She came in and shut the door. Now mind you, I don’t mind being almost naked with Karen. Hell we’ve seen each other on to many occasions for it to bother me. She came and sat on the bed.
She smiled and said, “You still are one of the hottest guys I have ever known Sweetie…….. I just wanted to make sure you weren’t to weirded out by this morning and running into Chrissy.”
“No…. I’m okay… Just wasn’t expecting to see her up yet….. I hope she didn’t feel uncomfortable. Because I did stare some at her. Kind of hard not too, dressed like she was.”
Karen laughed, “Oh Shit Honey. She loved that you did. She’s a bit of an exhibitionist. Plus, she thinks you are hot. So do I for that matter. And to be totally honest here, we used to walk around here naked all the time. So ponder that thought for awhile.” then winked at me and came up and patted my ass as she kissed me on the lips and left my room.
“Holy Shit” I thought. If I had to see them naked around here, I’d be walking around hard all the time.
We later then went to this Italian place and were seated in this curved booth. Again, Chrissy was in the middle and made the comment, “I’m starting to like this Chocolate Oreo thing we got going on.” and winked at me. Karen and I both laughed. Although, I would like to see it and we’re all naked and playing. Now that would be fun.
As we ate, Karen asked if I had any plans for the next night. Of course I was a smart ass and said, “Oh Yeah… I’m going to go out with all my friends that I know here.” then laughed.
“Smart Ass” she said… then, “We have to go to this party for a client and would love for you to go with us. It would give you a glimpse into our world and I want you to see what we do. You’ll need to wear a suit and tie, if you are cool with that.”
I chuckled and said, “A suit? Been awhile since I wore one, but I can accommodate you two lovely ladies. So Yes. I will gladly go.”
“Awesome” Chrissy said, as she leaned over and kissed my cheek. Towards the end of dinner, Chrissy almost made me spit out the bite of Cannoli I had in my mouth, when she asked,
“Vanilla.” I guess this is my new name now……… “How come you never screwed my girlfriend back in the day?…. I mean you two were so close and you guys even did oral to each other, but not fuck?”
I looked at Karen, thinking that she must of told all to Chrissy, since being with her. Karen just smiled and shrugged her shoulders, like, “What can I say. She’s got no filters”
I paused for a second, but then answered truthfully. “Honestly… I would not have “Fucked” her. Make love yes. She was, and still is, my best friend, and I thought crossing that line would have ended our friendship, had it gone wrong. And I never want our friendship to ever end because of that. I mean we were as close as two people could be. I know I loved her then, and still do, so that will never change. But, did I want too? Oh hell yeah. To me, she was, and still is one of the sexiest women I know. Actually, you both are. But I figured if it was meant to be, we’d cross that bridge when we come to it, with both of us feeling the same way.”
Chrissy smiled then said, “Thanks. You are one honest man. Not too many of you around.”
I looked at Karen and could see she had a little tear in her eye, so I broke contact with her. Now after baring my soul to Chrissy, and her, I was afraid that would complicate things between us. We then went back to finishing up. After I paid the bill, we headed home. I let Karen drive, since she knew her way around, while I sat in the back seat. It was a very quiet ride.
After getting back, I excused myself and went to my room, Stating I needed to go over some files from work. It was a true statement, but they could have waited until the morning at work.
I was just laying on the bed, my back against the headboard, with my laptop on my lap, go figure. That evening I wore black boxers, so that was all I wearing when I first got down to business. I heard the girls go to their bedroom around 10pm. But tonight, I didn’t hear any moaning and stuff, like the bed squeaking. I can only assume they get into strap-on’s or other toys.
About 10:30, there was a soft rap on my door and it opened. Karen walked in, closed the door, but not fully. She was wearing a long t-shirt. God her legs so good. I have always loved her long legs. She came in and sat on the edge of the bed.
“Can we talk?” she asked. “Of course we can.” I said
“About tonight. I am sorry. Chrissy sometimes needs a filter on her mouth. I know what she asked put you on the spot, and I really apologize for it. She is sorry too and will tell you tomorrow. She’s sleeping now.”
“It’s okay Kar. It really is. I was honest, like I have always been when it comes to you and I, and that will never change. I wasn’t mad either. Just wasn’t expecting that one though,” then chuckled. Then I sat the laptop down on the nightstand. The only light we had was from the small lamp on it too.
“I know, and like you, I have never lied to you. I too have loved you for most of my life. I wanted to make love to you back then, but I also didn’t want to lose our friendship, or for you to think I am some slut.”
“I would have never thought that of you. Never.” I said.
“I know, but back then, we both wanted to, but were to scared. I was also afraid had we, we would have dated until college and then it would end, and that would have kissed our friendship goodbye. Christ. Remember when we were dating in our junior year?”
“Yeah. You were with that Jim guy and I was with Britney. They were our first for going all the way, and we even shared the experiences.” I said with a chuckle.
“Yeah. tell me how many people do that, when they are the opposite sex. I hated her deep down too. She wasn’t good enough for you, in my book, and to be totally honest, she got what I always wanted.” she said, as she shifted some so her one leg tucked under her and her thigh touching mine, and her other leg still on the floor.
“So you were jealous huh?” I said with a laugh… “Shut up Ass” she said.
“Well I was jealous of him too. When we did it that night, and for any time we did it. My eyes were closed and thought only of you, to be honest here.”
“Oh My God. You too?……… I did that too, thinking it was you…. In fact, remember the guy I was living with, and even the married guy I dated? They never heard those 3 words cross my lips. No way could I say those to them. The only other person, besides you, that I told them that I love them is asleep down the hall.”
Then she stood up, grabbed the hem of her t-shirt and brought it up and over her head, and stood before me, naked. I sat there and just soaked in her beauty. I hadn’t seen her since that last summer before college, naked. Now my other brain started thinking for me, because my cock was starting to rise.
“Kar? What are you doing Honey?”
“Something that I have waited, what, 23 years for. We met when we were 10, so yeah, 23 years. Make love to me Sweetie.” as she grabbed my boxers and pulled them down, then off of my legs. My dick was almost hard now.
“But what about Chrissy? I don’t want to jeopardize your relationship.” I said, as she stroked me hard now and was swinging a leg over me to straddle me.
She grabbed my cock now and cooed, “Damn. I forgot how big you are. We’ll go slow until I get used to it. And, as for Chrissy. She knows Honey. We’ve talked a lot about this and she is happy if it happens. And, she also wants to experience you and I want her too as well. So let’s not talk no more and just make love, like we’ve always wanted too”
She was tight, almost like a virgin, tight. But after a few moments, she started rocking back and forth, then up and down. She and I both moaned a great deal, and she even came not even 5 minutes into it. The whole time her and I kissed as we made love. As she came she whispered she was cumming and that she loved me. I too professed my love to her and came about a minute after her.
Then, not wanting it to end, I was about to roll her over and do her again. But I caught a movement in my eye. It was Chrissy, clad in a t-shirt as well, smiling at me as she rubbed her pussy. She put a finger up to her lips, telling me not to say anything. This was now sensory overload in my book. One gorgeous creature making love to me, and the other watching and getting off from it.
I did then flip us over, without leaving her and slowly sank back in. Her tongue was exploring every inch of my mouth as I started the slow love making I hoped would never end after this night. We were in no rush to end this. It felt so right, after all these years. But then I had a thought. “Christ, no condom..Fuck”
I broke the kiss and asked, “Is this safe for us?”
She giggled, “To late now, Huh?… But yeah. Remember back when I was 14 and mom put me on the pill? I had to , to regulate my period and have ever since. Cum in me as much as you want.”
About 10 minutes later, she said “Speed up Baby. I need to cum and I want you to cum with me.”
That’s all I needed to hear and did like she suggested. About 2 minutes later, I could feel my balls tingle and that rush of cum start to rise up from my balls. Then she started to cum, and I released just after she started. I pumped a lot of cum deep inside her, as she washed my cock with her nectar too. She was biting her lip so she wouldn’t scream out. I knew from our teen years, when she cum’s, she get very loud. I too stifled my loudness.
We lay there a few moments, then Karen looked up at me and smiled. That relieved me. I was still have hard inside her. Then she smacked my shoulder.
“Ouch… What was that for?” I asked……
“Asswipe…. You should have done that to me 15 years ago… My God Blake.. I’ve never made love to someone like that.. God. I love how you feel inside me… How much cum did you pump in there. You’ve been storing that up for awhile I see, or better yet, feel.”
I chuckled and said, “It’s been a couple of months. And you are right, we should have done this way back then…..God. I love you Karen and always will.” then I whispered in her ear. “We had an audience”… she whispered back, “I know.. I caught sight of her when you flipped us…That turned me on. One night the 3 of us have to play. You need to watch us make love.”
“God.. I don’t know Kar…. Think Chrissy would want to do that?” I asked.
She laughed. “Be honest Babe. I’m sure you could hear us a few nights. She wanted to come get you a couple of times. You had to have been stroking this gorgeous cock of yours too.”
I laughed now. “Guilty… You two do sound very sexy together.”
I got off of her then and lay by her side. Her hand stroked my face a few times then told me about the next evening.. She explained that her boss, and his wife, was going to pick us up in a limo and take us to a penthouse that she and Chrissy helped remodeled.
“Not sure of your taste, but these people wanted a very contemporary look, so it has lots of chrome and glass. Now one thing Blake. All the people there are going to be rich, and are a bit eccentric. There’ll be plenty of booze and of course weed, but they also like to indulge in coke too. They all think Chrissy and I are lesbian, so let’s leave it at that, then they won’t hit on us.”
“I promise I won’t embarrass you. I know how to deal with snobs. I have run into a few in my field as well. Just tell them I am your gay brother.” the chuckled.
“Also, Annette, she is my boss, Bill’s wife. She is a big time flirt and loves younger men. She is like 45. Bill is 55. So she’ll definitely flirt with you. Bill wouldn’t mind either because they are swingers. I won’t lie, Chrissy and I have partied with them a couple of times.” she said as she ran her hand over my chest.
“You’re gonna make me hard again, if you keep doing that.” I told her
“If I wasn’t so tired, I would make you hard again. Trust me, this will not be the last time we do this. I may even let you fuck me too. Plus, I have this feeling someone is going to want a snack when I get back in bed.”
“You guys are bad.” I said………… “Not bad Baby. Just living life to it fullest now, and I want you part of it, but only if you want to be.” she cooed to me in a soft voice
“I love you Karen. I’ll do anything you want for now on. No more holding back.” I said, as she got up, told me she loved me too, and headed off to bed.
Chapter 4
I left for work as the girls were getting ready for work. I decided to knock off early for once, seeing it was a Friday. I texted Karen and told her I would get pizza for dinner, so we could have some food in our belly’s before we went to this thing tonight, since they would have finger food and booze only. She thought that was a wonderful idea.
After eating we all went and got ready. I was downstairs awaiting them, when they made their way down. Karen was dressed in a shiny, sequined black cocktail dress. It hugged her body do nicely. She had her hair up and a little makeup on, but looked smoking hot. The I saw Chrissy. Her brown hair was in a bun and she had on a white cocktail dress that blew me away. I wanted to suggest just staying home and let me remove them from their hot outfits.
I just stared… “Cat caught your tongue Sweetie?”
“You 2 look incredible. Absolutely Beautiful” I somehow managed to spit out.
“Thank You Vanilla. Think you can handle being with two of the hottest women in Chicago, let alone living with them?”
I chuckled and said, “I’ll give it my best shot ladies.”
The limo was there, right at 7. After getting in, I was seated next to Chrissy, facing Bill, Annette and Karen. After the introductions were made, we settled back for a 20 minute ride downtown. Bill and Annette were very nice and Bill was eager to learn about what I did. I did notice that Annette had placed her hand on Karen’s thigh, but didn’t want to stare.
At the party, most of the people were cordial towards me, not knowing who I was. Karen and Chrissy were showing me all around and what they had done to this place. It was gorgeous, just not my style. I know the rich like it, so to each his own.
Chrissy steered me towards the balcony and once out there she asked if I would like some weed. Since I wasn’t driving, I said sure. About 2 minutes later, Karen found us, and indulged as we did. We did see one couple snort some coke from a tray that was laid out there as well. I guess this high up, you can be a little freer in what you do. Chrissy even whispered to me, “Fuck. That would be fun to do, if the 3 of us were alone.”
Then about an hour later, I was chatting with some guy, who I never got his name, while the girls were explaining something to a potential client, when Annette came up to me and hooked her arm in mine. She steered me away from the guy, saying he’s an old windbag.
Then she kind of shocked me, when she said, “You know, this place has 6 bedrooms. I bet we could find an empty one and fuck for a good 15 minutes and no one would no we were even gone.”
I chuckled and said, “I don’t think Karen would like her gay brother fucking her bosses wife?”
She laughed and said, “You are funny. You are about as gay as I am the pope. I’m sure she wouldn’t mind.”
“Maybe she wouldn’t, but not in this setting. Some other time in a more friendly place.” is all I could come up with.
It was around 10pm and Karen found me and said it was time to leave. She said Bill told her to use the limo, but send it right back after we were dropped off……. During the ride, the girls were all happy because they have 2 more potential jobs coming their way.
“Besides the work you did was fantastic, it also didn’t hurt that you 2 were, by far, the hottest ladies there. I saw that most of the men were checking you out, except for that gay couple.” I said.
Both ladies smiled and Chrissy said, “We aim to please, and if you have the assets, then why not show them off…… And thank you for the compliment Vanilla. You look pretty hot yourself…. MMMMMMM”
Then I proceeded to tell them about Annette and what she wanted to do, and my response back to her. Both girls laughed and Karen said, “See… I told you she would hit on you…She likes young dick. She’d love using yours for a night, trust me there, and you would walk away fully satisfied. She loves to fuck.”
I was processing what Karen was saying. This was a new side to her that I really never knew. Her freedom about sex and all. I’m not complaining mind you. When we were kids and teens, true we talked a lot about sex, but it was a more reserved style. I for one, was enjoying her new side, as an adult.
Once home, the girls went upstairs. I went and got a beer, as I loosened my tie and took off my suit coat. I only had one beer this night. I was pretty lit from the weed for a partial time. After about 15 minutes, I figured they weren’t coming back down, so I turned off the lights and went up to my room. I looked at their bedroom door and saw their light on, but no sound was coming from it.
I just had hung up my trousers when the door flew open. There stood Chrissy with a wicked look on her face and a small robe on. Damn she looked hot. I was just dressed in boxers, and nothing else.
“Fuck” she said. “You look so hot Vanilla”…. Then she came to me and grabbed my hand, “Come with me….. Better yet, Cum in me later” as she led us out the door and to their room.
When we arrived, Karen was sitting on the bed with a robe on as well, and a few toys laying there too. Then I looked around and saw a mirror with a white powder on it. “Fuck” I thought. Sure Karen and I dabbled a couple of times with it, and even with my then live in girlfriend, we had tried it too. But it has been that long.
“Surprise Baby” Karen said. “I think you need to join us tonight. Seeing that Chrissy is my best friend, and so are you. And best friends always share. So let’s share each other.”
Now like any man, it has always been a fantasy to see two women getting it on, then letting you join in. So I was just going to go with whatever happened tonight. They invited me into this, so they must want to do this. I definitely like the newer version of Karen. I loved the old, but this is really cool.
Chrissy had me sit on the bed as she retrieved the coke. We each did a line, then she put the mirror back. I saw a vial sitting next to it then, so I had to ask where they got it.
Chrissy chuckled then said, “The client whose place we were at tonight. I saw him after we smoked that weed and asked if I could get a small bit from him. He laughed and said, that I could take as much as I wanted. Consider it a bonus…… I wasn’t greedy, so I took one of those vials. Hell, there had to be 10 more there.”
After doing the line, Karen asked, “You ok doing this Blake?…. I mean we don’t do this often, but just like when we were teens, it’s a great high, and if I remember from that one time we did it, your cock stayed up half the night. My jaw was so tired that night.”
Chrissy then asked, “When did this happen?” Karen giggled, “When we were 17 and his parents were over at my house, so we hung out at Blake’s. Somehow we got a hold of some and tried it out. Then we started making out, which was a norm for us. I sucked him for almost an hour before he finally came. And I know he ate me just as long”
“Fuck that” Chrissy said laughing…. “If that thing between his legs can go an hour, I’m not sucking it that long…. I’m fucking it…. But first, I need my Sugar.”
Chrissy dropped her robe to the floor, exposing her chocolate delight for me to see. My cock was growing just looking at her. Her long legs were toned and her sex was shaved smooth. Her breasts were just what I thought they’d be. Firm, but bigger than Karen’s, with dark brown areolas, and dark nipples perched on top, sticking out, begging to be sucked.
“Like what you see Blake?…. Want some of this Chocolate?” she asked seductively.
At first, all I could do is stare, but then said, “You are beautiful Chrissy. You both are” I said as Karen removed her robe now, and scooted up on the bed more, and then spread her legs for her lover.
As Chrissy climbed on the bed, she said, “Wait…. We’re naked, so you got to be as well Vanilla. I’ve waited long enough to see that cock of yours”…….. Then moved to me and took the waistband of my boxers and slowly revealed my hard cock. She threw my boxers across the room, then said,
“Ohhhhhhhh Fuck, Sugar. Give me one good reason you didn’t fuck that every second you two were together as teens?”
But neither of us answered, and it did not matter for Chrissy was between Karen’s legs now licking her slit. I just lay next to Karen and watched as these two made love. Karen was moaning a great deal, as Chrissy ate her pussy and even her ass. Karen did reach over and stroked my cock some as Chrissy worked her magic. I could hear Chrissy slurping away on Karen’s pussy now and Karen was getting ready to explode.
“Ohhhhhhhhhh Fuckkkkkkk Bitchhhhhhhhh..Cummingggggggggggggggg”
Karen’s ass came off the bed, like she was shoving her pussy into Chrissy’s face. Chrissy was drinking whatever nectar Karen was supplying too. I was so turned on by watching them. Chrissy then moved up so she was on top of Karen, and they kissed. I heard many muffled “I Love you’s” between them. At this point I kind of felt like a Peeping Tom.
Then Chrissy rolled off of Karen and was right next to me, so I moved a bit to let her stretch out. Then she spread her legs wide for Karen. Karen wasted no time in getting between them and started returning the ministrations that Chrissy so expertly just gave Karen.
In my wildest of dreams, would I ever think to see Karen and another woman together. But, here I am watching these two beautiful ladies make love to each other. But as I watched, Chrissy reached over and grabbed my cock, and pulled on it, signaling me to come closer to her mouth. So I knelt near her face and she took my head into her sultry lips ad began to suck it. Fuck, I thought. I looked down at karen, whose eyes were now locked with mine, and I saw her smile. That made me feel better. Granted, we are not a couple, so I wasn’t cheating. If anything, these two were bringing me into their world. I won’t lie though, I am in love with Karen, and always will be, even if this is a one time deal.
I then leaned down and took one of Chrissy Hershey KIss nipples into my mouth and sucked away. They were big and hard, and I could see why Karen was so attracted to her. Chrissy was moaning loudly, and the vibration on my cock felt so good. Then a few minutes later, I had to straighten up. That’s when Karen tapped me on the arm and crooked her finger to me to join her in licking this gorgeous pussy.
I moved a bit so I could lean down and lick her mound, but my cock popped from Chrissy’s mouth. Chrissy told me to straddle her head, which I did, then proceeded to suck my balls. Both Karen, and my tongue started working her pussy. She tasted divine too. At one point, Karen and I kissed and licked each other’s tongues, sharing Chrissy’s juices.
“Oh Fuckkkkkkkkkkkkkkk……….. You two are driving me crazyyyyyyyyyyyy, you Fuckerssssssssssss” Chrissy yelled out.
Karen kissed me again, but then moved away, which left me alone with Chrissy’s pussy. I dove right in and licked her harder now. I let my tongue stray down to her puckered ass and licked her brown hole.
“Ohhhhhh.. Fuck Yesssssss…… Lick that ass Baby”
Then I felt the bed move some, and looked up. Karen was on her knees, with a strap-on attached to her. I then moved out of the way, and swung my leg back over to give Karen all of Chrissy.
I just sat there and watched as my best friend started to slowly fuck her lover. Karen was on her knees, and just slightly bent and holding onto Chrissy’s raised knees, as she pumped in and out of Chrissy’s pussy. It was a very erotic sight, at least to me, since I’d never seen live action like this. What was turning me on too, was the loud moaning and dirty talk between them. Like I said, I’ve never seen this side of Karen but I was truly loving it.
“Huh Baby… You love that cock don’t, my little slut?” Karen said to her.
“You know I do Bitch…. You gonna let me have some of Nilla’s cock later?…….By the way Nilla, I love the taste of your cum.” Chrissy said as she smiled up at me.
I chuckled, then thought how she loves calling me Nilla, or Vanilla, so I think I need to give her a nickname too.
“Well Coco, maybe you need to get it right from the source later” I said to her, which made Karen laugh a little, as did Chrissy.
“Wooooooohooooooo. I like the name Nilla… Can’t wait to feel that big cock in my brown sugar of a pussy…….. Oh Fuck Baby.. Fuck me harder.. I’m almost there.”
Karen did start fucking her harder. I liked watching both girls tits bounce all around, but then Karen lay on top of Chrissy now and Chrissy’s legs wrapped around Karen’s waist, as she started to pound into her.
“Oh God… That’s it… Right there…….. Ohhhhhhhh Fuck….. Make me cum Bitch”
“Take it Slut.. Cum all over my cock” Karen shouted…
These two were so into it now, they probably forgot about me being there. Then Chrissy let out a long, loud cry as she started cumming. As she came Chrissy bit down on Karen’s shoulder. That set off Karen who started crying out that she was cumming too. As they came, I was rubbing Karen’s back and ass with a slow, caressing hand. Her skin actually had goose bumps from their orgasmic session. Each even had a slight sheen of sweat going on, which in my mind, looked very sexy on them. As they rested and kissed, I got up, and went downstairs and got us some bottled water.
As I re entered the bedroom. Both girls were not sitting against the headboard. Chrissy had the mirror again and they just must have finished a line, since only one was left. “Oh well” I thought. “Might as well go with the flow here”. I handed each a water, then leaned over and took my line. Damn that shit burns.
“Good, Huh Baby?” Karen asked. “Yeah…. Probably pay for it in the morning though.. Been a few years for me.” I said
“We don’t indulge much either” Coco said (Chrissy’s new name) then said, “Wasn’t that Christmas party at Bill and Annette’s our last time Kar?”
Karen laughed. “Yeah…. That was a wild night…. Remember those two guys you thought were gay tonight?” she asked.. I nodded. “Well they live together and sleep together, but they are Bi as well.. Kind of like me and Chrissy…. But we played with them that night. And, Annette fucked every guy that was there that night…. Very Merry Christmas time.” then she laughed.
Karen was still wearing the toy, when, for some unknown reason, I bent down and licked it, then put it in my mouth and sucked on it, tasting Coco’s delicious juices.
“Damn, Nilla.. That’s so fucking hot….You can be Bi with us anytime Baby.”
My mouth popped off of it, and then my mouth moved down a bit to her pussy and started licking it. Karen sucked in a hard breath as my tongue ran over her clit. Coco then leaned over and took the fake phallus into her mouth and sucked on it. I looked up and saw Karen pulling on her nipples, with her head moving back and forth.
“God Damnnnnnnnnn you Fuckerssssssssssss……. Blake Baby….. Fuck Meeeeeeeeeeee” Karen yelled out.
Damn good thing her condo was an end unit and their bedroom wasn’t with the common wall. I pulled a pillow out and placed it under her ass, and then kneeled between her legs and slipped my cock inside her. Coco rested her head on Karen’s stomach and continued to suck that toy.
“Oh Fuck yeah Baby….Fuck my pussyyyyyyyyyy………..Awwwwwwwwww”
Never one to be asked twice, I started fucking her. This wasn’t like last night and our love making session. This was pure animal lust, that primal need in both of us coming out. Her hips were moving up and down to try and take all my cock in her. I even grabbed her legs behind her knees to give me better leverage.
Coco, meanwhile, got up and straddled Karen’s face and was being eaten now by my hot little vixen. As I kept up my pace, I could feel Karen tense up and let out a loud squeal as she came again. Neither Coco, or I, stopped while she came. Coco was staring me in the eye as I continued to fuck my best friend. Then she loved her face forward and kissed me. Her tongue shot into my mouth and was tongue fucking my mouth.
Karen meanwhile was building up again to an orgasm, and so was Coco. I have no idea how Karen could concentrate on eating her, and being fucked too. She’s a great multi-tasker. One other thing, when a man is on coke, at least for me, it takes a lot longer to cum, and I was nowhere close. I was moving now even faster, as I broke the kiss with Coco.
I heard a muffled response from Karen, “Fuck Yeah…. Right there Baby… Fuck me harder, I need to cummmmmmmm”
I pushed her legs back more and pounded inside her. I was rewarded by Karen’s pussy clamping down hard on my dick as she began a long orgasm.
In a deep voice she yelled, “Godddddddddddddddddddddddddddddd” over and over.
Coco too, started to cum. So with my dick still inside Kraen, I leaned in and lightly bit on Chrissy’s one nipped, which made her keep cumming too. After a minute though, Coco fell over onto the bed, her body twitching some. Karen was panting hard, as I was too.
I leaned down and kissed Karen and told her I love you. She said it back to me, then got a weird look on her face. Next thing I know, she smacks my arm again.
“You Asssssssssssss………..I’ve been missing out the last 15 years of this…….. Bet your ass on one thing Slick……I’m not missing another 15 years.”
“Goes both ways you know…….You could have said something too….. And, had we stayed together and were lovers, you wouldn’t have met Chrissy.” I said
Then Chrissy piped in, “Now that would suck……But were all together now, so forget about the past, so let’s just move forward. Tonight has been great, so far. Hope we’re not done.” she said, and then laughed. Hope not either. I’ve wanted to be inside Coco ever since I met her.
Karen laughed and said, Hell no we’re not done. Stud boy needs to give you some of that dick of his…… God Baby, he knows how to fuck better than anyone I have ever been with.”
Chrissy crawled over to me and pushed me down, and on to my back. She crawled then between my legs and took my cock into her mouth and began to suck it. God her sexy lips so good on my cock right now. She was looking me right in the eye as she did this. Karen moved over and was playing with my chest and nipples, and then kissing me.
Karen whispered, “You like that Baby? You like her sucking your big cock?……… Fuck you two make a sexy couple.” she cooed
Then Coco quit sucking and moved up and straddled me and slowly slid my cock inside her tight pussy. Hers was even tighter than Karens. I was in heaven now. I wasn’t sure where Karen and I were headed, but I’m pretty sure we’re going to be more than “Just friends”, and now she is sharing her lover and best friend with me.
“Oh Fuck” Coco said….. “What a cock…… You like Coco’s hot pussy Baby?…… You like that chocolate cunt riding your vanilla cock like this?”
Not wanting to kill the mood, I answered, “Fuck yeah baby.. Your pussy is as good as the finest silky milk chocolate known to man… Ride me Baby… Fuck my cock”
Then Karen swung her leg over my face and lowered her pussy to my mouth. For the next 10 or 15 minutes, I ate Karen while Chrissy fucked my cock. I could hear them talk, but couldn’t understand them. Karen came again because of my tongue, which then set off Chrissy. Her nails dug into my biceps as she came, and they both were squealing loud.
Then Karen rolled off of me and landed on her back, panting hard… “Oh fuck… Cumming so much tonight” she said.
Chrissy pulled off of me too and lay on her back and spread her legs wide, and rubbed her pussy. She smiled at me and said, “Get in her…. I want your cum Baby….Fuck me hard and fast and give me your cum”
This time, I had no hesitation to that invitation. I got between her legs and slammed it home. “Ommmphhh” she went. Her legs were held out wide, to each side as I started to fuck her. I pounded inside her…. Her hands were like vise grips on my forearms. Her pussy was tight, and very hot. The bed was bouncing all three of us too, with Karen just laying there, watching her best friends fuck each other silly.
I pushed Coco’s legs back so her knees were by her head and really started to slam her..
“Oh Fuck Yessssssssss… Right there Baby… Fuck me just like this, you Fucker”
After a few minutes I could feel my balls tingle and I knew I was close. So was Coco. Her moans were super loud now, and I was grunting loudly. I let go of her legs then and placed my arms around her neck, and she did the same to me, then wrapped her legs around me.
“Oh Fuck Blakeeeeeeeeeeee. Cum in me…. Cum in me”
I did, as I let out a loud moan and grunt. I pumped at least a gallon of my seed deep inside her. When we calmed a bit, we were both holding each other tight. She is an amazing lover. Both are in fact. I felt like the luckiest man on earth actually.
After moving off of her, so she could have some air and catch her breath. Karen got between her legs and licked her pussy, cleaning our combined cums from it. Chrissy and my head were touching as we watched my baby eat her. Then Karen came up with a mouthful of cum and started kissing Chrissy. Karen pulled on my head to kiss me too, which I gladly accepted. Then we all licked each others tongues, together.
About 5 minutes later, Chrissy shocked me when she said, “I’m done for the night. I can’t move a muscle”. Karen said basically the same thing. I was whipped too, but still ¾ hard. I got up and went to the bathroom. When I finished, I opened the door to see Karen there. She pulled me into a hug and kissed me.
Then said, “I love you Blake…. Not friend love, but real love… Sleep in our bed tonight.”
She then went and peed, and I went back to their room. Chrissy patted one side of the bed next to her. “Come her Nilla and kiss me”, which I then did.. Karen came back into the room and turned off the lamp and crawled in next to Chrissy. We three then did another 3way kiss and said good night.
Then Chrissy said, “Look Nilla, you better not fucking snore”, which made all of us laugh.
Chapter 5
My head was pounding, which woke me up a lot sooner than I wanted too, see it was a Saturday. I quietly got out of bed, and looked down to view the girls holding one another, but peacefully sleeping. I grabbed me boxers and put them on and went to the bathroom, then downstairs to make coffee.
I sat there for almost an hour, thinking back to the whole night before and everything that took place. The tylenol was finally starting to kick in then too. I was a bit nervous on how I would be perceived now by the ladies, since we shared what had to be, the most sexual night of my life. That answer came about 30 minutes later.
Karen came down the stairs, still naked, and looking pretty good, for the amount of partying we did. Just looking at her has always made my heart beat faster, even when we were teens. When I saw her, I got up and went to the coffee pot and got her a cup. She saw me getting that and smiled.
“Good Morning Sweetie… You must be a mind reader. I need a cup badly.”
I handed it to her, then she looked at me and shook her head… “What?” I asked….. She frowned, then said, “Before you came into our lives, our dress code was how I am now, so lose the boxers mister.”
I just chuckled then removed them and sat in a chair by the kitchen table. Karen came over by me and placed her cup down and then straddled me and sat in my lap.
“How are you feeling Blake?.. You look like shit.” she asked
“Feeling better now. Woke up with a pounding headache. But now feel a lot better, especially with you sitting here…. I was worried about how you would be this morning.” I said
“I feel great… I made love with you two last night…. Ok.. We did fuck a lot too, but still. I was with the two people I cherish most in this world…. Blake I have a serious question.”
“Okay… I’ll answer it as best as I can, honestly.” I retorted
“I think we both can safely say that we are, and always have been, in love with each other.” Karen said as she kissed my forehead. “Agreed”
“Can you honestly handle an open relationship between us 3?” she asked….. I looked at her, but didn’t answer. I was trying hard to process this.
“What I mean is this…. You and I make love….. You and Chrissy make love… The 3 of us make love together, and we live together, and share the same bed too.”
“You’re serious aren’t you?” I asked.
“I am so very serious… Chrissy and I spent the last 45 minutes discussing this. If you couldn’t tell, she likes you a lot. But she is all for it. She could see herself falling in love with you too, like I am….. Baby, we made a huge mistake 15 years ago and not tell each other our true feelings. Had we, I really think that we’d be very happily married and have kids…. But I don’t want to lose you again, and I don’t want to lose Chrissy either.. I know it sounds fucked up, but we want you Blake, and not just sexually. We want all of you.”
“You are so right Karen….. The only reason I never married is because every woman I would even consider having a relationship with, had to meet my standards for love, and I based that on your love, and the love we shared.”
“But” I said……… “Will there be any jealousy?.. I mean what if you came home one day and Chrissy and I are making love. That won’t bother you?”
“No Baby, I won’t. I think the 3 of us are pretty open minded and can handle this. I don’t want to lose you again, for any reason, and I don’t want to lose Chrissy either…. Just like I know it won’t bother her if you and I are alone making love, and trust me, we are going to be doing that alot for now on….. I’ll tell you when I got jealous. It was last night when you said Annette wanted to fuck you at that party. I got real jealous, and so did Chrissy. Annette’s got enough dick to take care of her. If you look at it from our point of view, why would you need anyone else when you have the 2 sexiest babes around. And whether you want to admit it or not, you are pretty damn sexy yourself.”
I chuckled, then said to her, “Yeah. She caught me off guard asking for sex from me. One thing I know for certain, I’m going to have to start working out more. Keeping up with you two in bed is going to be a feat.”
She kissed me, as her arms went around my neck. We kissed for a good minute, before she stopped then said to me.
“Good… So forget about finding a place to live, this is your home now…… We’re your loving family…… Now I am going to shower and then head to my office…. I have to set up a program for our construction unit to do on Monday. I should be gone just a couple of hours…. Be a good time for you and Chrissy, or Coco as you like to call her, get to really know one another, if you know what I mean.”
She kissed me again, then got off of me, leaving me with a hard on… Of course as she got off, she squeezed it, then giggled and told me she would see me later. She did reappear about 30 minutes later, dressed in jeans and a polo shirt. Damn, her ass looked great in jeans. I asked where Chrissy was, and she told me still sleeping. Someone kind of tired her out last night. She then kissed me and we exchanged “I love you’s”, then left.
I sat there for another hour thinking, and processing everything Karen had told me. There was a lot of “what if’s” to consider. I have always thought of myself as a progressive type of guy, and open minded. This would definitely need open mindedness, that’s for sure. I definitely am intrigued by everything. The Bi side of the girls. Their openness to explore sexually. The biggest question is, could we do this and not have jealousy, and, could my body take this. But the biggest is, what about our parents?
Part 2 soon