Former Roommates Connect

Part 1

I always thought my old roommate was gorgeous, but as I got to know her over the years I also discovered what a great person she is. She is caring and generous, as well as having a wicked sense of humor. Back when I met her, the fact that she had a great ass and gorgeous blue eyes was just about enough for me to agree to have her share my apartment. Just to be clear though, it wasn't a sexual thing when I offered her the room, it was just a feeling that this was a person I would get on with. Over the years I have been pretty lucky with this feeling, and it was certainly the case with her.

We have stayed in touch for the 10 years since we shared the apartment. In that time, she has gone from being a cute, somewhat ditzy 19 year old, to a successful woman in charge of budgets worth millions. We were chatting the other day when she told me that she felt like just getting away from everything. I suggested she come and visit me, and we could hang out and drink some red wine. Maybe visit a winery. I was a bit surprised when she immediately said yes, and even more surprised when, a week later, she confirmed her plans with me, to tell me she was coming over for a few days.

A couple of weeks later I picked her up at the airport. It is always great to see her, and we always have a long, close, hug. This time was no difference, and it was as good as it always is. Eventually we separated and headed to the car. We stopped off for a bottle of red wine on the way back to my apartment, but couldn't decide, so we ended up getting a dozen just in case! We got home, and I set her up in the spare room, then went to pour a couple of glasses of wine. I was sitting on the couch when she comes into the living room, wearing what I assume are her pajamas. In reality they were a flimsy pair of short shorts, and an equally flimsy T-shirt, with a really big collar, so the opening for her head fell over one of her shoulders.

'Jesus,' I exclaimed. 'I'd forgotten what your pajamas are like. I've only seen you wearing business clothes over the past 10 years or so.'

'Oh, sorry hun, I didn't think about it. Do you want me to change?'

'Of course not, dumbass,' I joked. 'You do whatever you want. You are the guest.' I was happy for her to wear skimpy clothes, but also wanted her to feel comfortable. 'Wine?' I asked, handing her the glass.

She settled down on the chair next to me, nestling down amongst the cushions. So much seemed familiar. We were just relaxing at home, like we did a long time ago. We were both older, but it didn't seem like it. Certainly not for her. She still had great legs and a great ass. And, as always, I couldn't stop looking at those huge big blue eyes.

'I can't believe how dumb I was when we used to live together,' she said, after we had been talking for a while.

'What do you mean?'

'I was such an idiot. Running around, partying, shagging, doing dumb things. I don't know how you handled it.'

'Don't be silly, that is what you are supposed to do when you're 19! As for handling it, it was kind of fun. It had been about 10 years since I'd done that stuff, so it made me feel young.'

She smiled, which made her eyes light up. 'Well, I'm glad. I'm also glad you didn't know about everything that went on.'

'I'm sorry?'

'Well, there were a couple of close calls.'

'Ok, this is getting interesting. Like what?'

'There were a couple of times you almost caught me naked when I was going from the bathroom back to my bedroom.'

'Damn, that's a shame. But it wouldn't have been my fault if you were the one walking through the living room naked to get back to your bedroom.'

'Oh, I know it would have been my fault. In fact, that was a bit of the thrill. That and being too lazy to put a robe on.'

'Thrill?'

'Well, a quick little nudie run in the morning gets the heart rate up. No harm done.'

'No harm?' I asked. 'I'm not sure what is worse, not catching you, or knowing that I didn't catch you. I think it would have been better not to know!'

'Ok, you really aren't going to like this then.'

'Go on,' I said.

'Well, one time you nearly caught me masturbating on the couch.'

'I beg your pardon?'

'You heard,' she said, turning a little red.

'Ok, I need the details.'

'Well,' she started, getting a little embarrassed. Then she hesitated.

'Ok, you don't have to tell me if you don't want to,' I said. 'I'll go first if you want?'

She seemed a little relieved, and more than a little interested.

'You almost caught me doing the same, except not in the living room, out on the balcony.'

'What! Outside?'

'Yup.'

'How?' she asked.

'Ok. Well.' Now it was me who hesitated a bit. 'I was tanning outside, and you know I don't like tan lines. You weren't home, obviously. Then I started getting a bit turned on. And then a bit more. So, I was lying on my back, tanning, and started rubbing myself. Suddenly I heard the front door unlock, so I bolted from where I was on the balcony, through the sliding doors direct to my bedroom.'

'Haha, that's so funny.' She hesitated, then seemed to make her decision. 'Well, what did you do then?'

'You want details?' I asked.

'Sure, why not,' she said confidently.

'Well, I was in my bedroom. Then I realized the bedroom door was open to the living room. But I couldn't close it without you seeing me. But I heard you going out onto the balcony. Now, the bedroom door was open and so was my screen door to the balcony. The towel was on the ground outside, so I assumed you would know I was home. I was kind of standing there, trying to work out what to do.'

'Oh,' she said. 'I think I remember that day. I thought: that's weird, there is a towel on the ground, he must be home. Then I wandered over to your screen door and saw it was open.'

'And what did you see?'

'Nothing in your room.'

'That's because I had grabbed some shorts and a shirt from the floor and gone around to the living room. I was putting them on as fast as I could. I almost tripped over putting my leg into the shorts.'

'Ok, now I definitely remember. I assumed you were tanning. Then I turned around and saw you inside and was surprised and thought maybe I was wrong. It is a pity really. If I'd known you were fine with tanning on the balcony I would have done the same myself.'

'Naked?' I asked.

'Well. Maybe not naked. But probably topless.'

'Damn. I really, really wish I'd known that then. That would have been awesome! But anyway, that's my story.' Then I stopped and let the silence encourage her to continue.

'Ok, well, you told me yours, so here goes.'

'Hang on, I'll pour some more wine first,' I said. Then she told her story.

'Let me try to remember. I was home by myself and decided to clean the house. You had your computer on the dining table, with some discs scattered around. I was dusting so I was moving things around and noticed that at the bottom of the pile of discs was one titled: One Night in Paris.'

'What? Whoops, sorry about that.'

'No problem at all hun. Now, where was I. Ok, so I saw it and thought, hang on, is that the movie of Paris Hilton? And I was curious. So, I took it and put it into the DVD player, and I discovered it was indeed the video of Paris Hilton. I was intrigued, so I settled down on the couch to watch it.'

'Just to watch?'

'That was the intention at the start. But then I started to get turned on. She is pretty hot. And, well, one thing led to another.'

'What thing led to what other?'

'Haha, you have a dirty mind.' She hesitated. 'Ok, rubbing my pussy on the outside of my shorts led to putting my hand down my shorts, which led to rubbing my clit and fingering myself. Is that what you wanted to know?'

'Yes,' I smiled. 'That is exactly what I wanted to know. So, what happened? How did I interrupt?'

'Well, like you, I heard the door open. Luckily, I was still clothed and the remote was nearby, so I just took my fingers out of my pussy, wiped them on my pants, and turned off the TV. Then when I had a chance I took the DVD out and put it back where I found it. Then, if I recall correctly, I went to my room for a nap,' at which point she did the traditional air quotes, 'and finished myself off.'

'Good girl,' I said. 'No point in leaving yourself hanging.'

'My thoughts exactly.' There was silence for a moment. 'So, did you finish yourself off after I almost caught you?'

'Nah,' I said. 'With the stress of almost being caught I got an instant soft on. That was the end for me.'

There was a moment of silence, then I decided to call it a night. 'Ok sweetie. I have to work tomorrow, you don't. I'm going to go to bed. You should stay up. And we can continue chilling and drinking tomorrow when I get home.'

'Aww, that's a shame. About tonight I mean. But I understand.'

'Ok, night sweetie.'

Then I went to bed. Before going to sleep I found the old Paris video on the internet and sent her the link: 'Here you go sweetie. Something to help you sleep, perhaps.' A couple of minutes later I got the response, 'Hahaha. Thanks, hun. I'll be sure to watch it. Love you lots.'

Part 2

The next night I got home from work and she had a glass of wine waiting for me. She was halfway through one herself. I assumed it was her first, but in hindsight, she may have started earlier. I went to my room to get changed into shorts and a T-shirt, then joined her in the living room. She was wearing workout gear, a tight singlet and tight little shorts. She looked hot.

'Been working out?' I asked.

'Well, I did plan to, but then ran out of time.'

'You ran out of time?'

'Yes,' she said. 'I ran out of time. And before you ask, it was your fault, and it was related to the link you sent me last night.'

'Hahaha. Ok, that makes sense. Good for you.'

'Really? I wasn't expecting that reaction.'

'Why not? Why would I mind?'

'Well, I guess no reason.'

'I don't mind at all. Because now I get to ask, how?'

'How?'

'How?' I asked again. 'You don't have to answer anything, but I'm always really interested in masturbation. How? Rubbing your clit? Fingering yourself. Sitting? Lying back? Lying on your stomach? Naked, or partially dressed? Dildo? Vibrator?' I paused. 'You know, how?'

'Hahaha,' she laughed. She was a little nervous but kept going. 'That covers just about everything I think. Ok, you asked. Outside on the deck. Naked so I could tan. Sitting on the chair with my legs over the arms. Rubbing my clit and a vibrator in my pussy. Anyway, let's move on. What's the plan for tonight?'

I hesitated for a moment, desperate to investigate all that information further, but she wanted to move on, so I had to respect that. 'I have no plan, apart from sitting down and drinking wine with you.'

'Well, sit your ass down then,' she said.

'Ok then,' I said, then I settled down on the couch. I smiled. 'It is so nice to see you sweetie. Having you here reminds me of lots of fond memories.'

'Me too.'

'Though I have to say, one thing is very different.'

'What's that hun?'

'Well, you fill in that singlet a lot more than when we used to live together.'

'Hahaha. I was wondering if you would say something! Yes, I have much bigger tits now. Back in those days the only reason I needed to wear a bra was to hold the chicken fillets so I had a little bit of cleavage.'

I smiled. 'Well, for the record they were great before, especially when you were wearing your pajamas in the morning and your nipples were sticking out. By the way, it always used to annoy me when you would cover them up. But I digress. They were good then, they are spectacular now.'

'Thanks, hun. I like them. Tits are awesome!'

'I completely agree,' I said. 'But I'm a bit surprised, my female gay friends have told me that they don't get why guys think tits are such a big deal, because they are always just there on their chest, so it is just normal for them.'

'Well, they are entitled to their opinion, but I am too. I love them. Could look at them for hours.'

'Haha. Well, in that case, I'm surprised you liked the Paris video. She doesn't have big ones.'

'Good point. But they are still a really nice shape, and she is really hot. And anyway, watching her getting eaten out is great no matter how big her tits are.'

'Hahaha, didn't think you would go there, but I couldn't agree more.' Then I got a bit bolder.

'So,' I asked, 'as a huge fan of boobs, have you ever played with any other than your own? Have you ever had a dip in the lady-pond?'

'I beg your pardon,' she replied.

'I mean, have you ever had sex with a girl?'

'Haha, is that what that means?'

'Yes. And the answer is?'

'The answer is no.'

'Really? Wow, that surprises me, especially with your love of boobs.'

'Well, I'm not really that adventurous.'

'Really? No offence, but that really does surprise me.'

'I'm really not. I like sex and may have made some mistakes when I was drunk, but never even kissed a girl.'

'Do you want to?'

'Honestly, I'm not sure. Women don't turn me on like guys do. And I really love dick, so I haven't really thought a lot about it. But I definitely find some women hot.'

'Like who? What's your type?'

'Haha. Ok. My type is cute and kind of fun and sarcastic. Jennifer Lawrence. Anna Kendrick. Kate Beckinsale. Alison Brie. Alice Eve.'

'Wow, you have thought this through, haven't you?'

'Scarlett Johansson, Charlize Theron, Mila Kunis.'

'Hey, those last two don't have big tits.'

'No, I know, but they are hot.'

'Yes, they are.'

'Do you need anymore?' she asked.

'Sure, one more,' I joked.

'Emily Ratajkowski,' she immediately said. 'I could look at her all day.'

'Haha. Me too. Thanks for that. I think I have a good impression of your tastes. And, for the record, I wholeheartedly agree.'

'Really? So, we have the same taste in women?'

'Haha. Yes, I guess so.'

'Ok, my turn now. Have you ever been with a guy?' she asked.

'Ha. No.'

'Want to?'

'No. I've actually thought about it a bit, because as you know, I'm a bit effeminate. But I really like girls.'

'Ok, fair enough,' she said.

We kept chatting about all sorts of things. It was one of the things I loved about her. We could talk so effortlessly and for hours. It was nice to just have that relaxed connection. As we talked we drank.

'Woah, just about finished the next bottle,' I said.

'Shit. That was easy. It also explains why I'm drunk now!'

'Yup, and also why it is dark outside. Crap, it's after 10pm already.'

'What do you mean, 'Crap'. Past your bedtime?'

'Actually, yes. But that is not what I'm suggesting. I was just a bit surprised it was so late already.'

'Me too,' she agreed. 'But it is no big deal, I don't want to go to bed yet. Want to go out?'

'Jesus, yeah, because I love crowded bars and noisy dance clubs.'

'Ok. I knew it was a long shot. You sure you don't want to go out dancing?'

I was pretty sure she was teasing, but I still replied, 'Very sure.'

We both took a sip of our wine and sat in silence for a short time. Then she asked a question.

'Well, this is your town, I'm assuming you know where the strip clubs are. What about that?'

This got my attention.

'I most definitely know where they are. You want to go? Look at all the lovely titties?'

'I didn't suggest it for you!'

'Well, in that case, I would love to escort you to a strip club. I've never gone with a girl before, and the idea of it really turns me on.'

'Really? Why?'

'I'm not completely sure. Just the idea of the woman being there looking at the strippers. I find it hot.'

'Well, I'm thinking much the same thing, so I can't criticize you for it I suppose.'

I smiled, 'Ok, let's do this. We should get changed into something more respectable.'

'Ok. Can I make a suggestion?' she asked.

'Of course.'

'Let's dress up. I'll wear a nice dress, and you wear a suit.'

'Done. That sounds kind of fun.'

We went to our rooms to get changed, then met back in the living room.

'Jesus,' I said. She looked incredible. 'You scrub up pretty well.'

She was wearing the classic little black dress. It was low cut and showed off her tits perfectly. Lots of cleavage. More than I'd ever seen before. It showed off her ass too. And she was wearing cute red high heels.

She smiled, 'Thanks hun. You look very handsome yourself.'

I went over and gave her a hug. She was already a little taller than me, and with the heels she was a lot taller, so my head was closer to her chest than her head. I turned my head and gave her a kiss on the exposed part of her chest.

'Cheeky!' she exclaimed.

I looked up at her, 'Sorry sweetie.'

She laughed, 'Don't worry, it was funny. No problem at all.'

With that we left, hand in hand, more than a bit tipsy, and heading to the strip club.

When we walked into the club there were more than a few heads turn to look at us. Well, her. I'm pretty sure this made us both happy. We sat near the stage, but not close enough that we were expected to be putting dollar bills in garters.

'What do you think?' I asked.

'About the place? Or the girls?'

'Both.'

'Well, the place is fascinating. Seeing the reactions of the guys looking at the girls is so weird. This must be what it would be like if social norms were different. There is no hiding or subtlety, guys are just staring at tits and asses.'

'I know, great isn't it!'

A hot girl in a skimpy outfit came over to us and asked us what we wanted to drink, so we ordered and started to look around the room.

'See anyone you like? Lap dance is on me,' I said.

'Awww, you are sweet. But I couldn't do it by myself, I'm too nervous. Can you come with me?'

'Nervous? Really? Why?'

'Well, this is pretty new to me. I know you've been before, but I haven't. And the idea of a dance is pretty hot, but pretty scary too. I've never done anything like it before.'

'Ok, that all sounds fair. I would love to have a lap dance with you, so, no problem.'

'Thanks hun.'

We continued to look around, and both of us ended up staring at an athletic girl with huge tits. Not that big a surprised! She saw us looking and came over to the table.

'Hi guys. Enjoying yourselves,' she asked.

We assured her we were. Then I got straight to the point.

'We were wondering if you could do a lap dance for the two of us?' I asked.

'Well, technically no,' she said, 'but I can do a private dance for both of you.'

I looked at my gorgeous friend, who looked at my quizzically.

'A private dance is in a private area out the back somewhere. Usually they are comfortable, we will be sitting on a couch, and this lovely girl will be dancing for us. Are you up for it?'

She nodded. So, I confirmed with the stripper and she took both of us by the hand and led us to the private lounges.

We sat down on the couch and the stripper started swaying to the music. She asked if we had been to a private dance before and I told her that I had, but that my friend, who was looking a bit uncomfortable, hadn't.

'You can relax sweetheart,' the stripper said to my friend, 'nothing will happen here that you don't want to.'

'Ok, so what will happen? What can you do?'

'Well, I strip naked and dance. I can sit on you and grind on you, but you can't touch me or grab me.'

My friend looked at me, then she smiled a little.

'Can you handle that,' I asked.

'I think so,' she said. And she turned around to the stripper again.

She took her top off and kept dancing so that her tits were bouncing. Then she moved over to me and slapped me with them. She was motorboating me, but her tits were so big it felt almost like a slap. They felt so smooth on my face and smelt great. I was smiling when she pulled away and looked over to my friend who was watching me closely.

'Would you like that sweetheart,' the stripper asked.