When you're in your early twenties, the world is open to you. You feel so invincible and that nothing is impossible. My aunt always told me nothing was impossible and if you didn't try, you would never know what your limitations were.
My girlfriend Clare and I watched a porn movie together when we were stuck in a hotel for a night outside of Indianapolis. We had always had great sex in our two years together, but I was feeling like something was missing. That movie we watched in the hotel room that night helped me figure out what it was that was missing.
There was a scene where two women were having sex and then a guy came in and joined in. I knew then, that I wanted that. I wanted the experience of a threesome, with Clare and one other woman. Clare fidgeted a little during the scene, but right after the scene, we were fucking like we hadn't done in a long time. And when I was ready to cum, I pulled out and pushed my cock into her mouth. I wanted to see how she'd respond tasting her own pussy juices and my cum at the same time. Watching my wet cock slide between her open lips just really sent me over the edge. She swallowed and didn't complain afterwards and I knew I had to have that threesome. The problem would be finding the third person.
My family split up when I was sophomore in high school. My father moved south to Florida to write a novel and fish. My mother took my younger brother and moved to California. I wanted to stay in my hometown, so I moved in with my Aunt Jenny. She had a house at the edge of town that sat on a couple of acres of land. Her late husband had been a farmer and when he died, she got the house and the land. Jenny wasn't the farming type, she liked the city more, but the house was big and comfortable and it was paid for.
Once a month she would go into the city and spend a weekend there. I always imagined she had a boyfriend there and she kept things quiet so she could continue to lead her own life in the farmhouse. She was an independent type who liked nice things and liked her space, she liked culture and considered herself a refined, worldly woman.
As far as looks go, Jenny was attractive, but not a beauty. She wore her make up well and kept her hair stylish, her large, almond shaped green eyes were her best asset other than her body. What men (and women) first noticed about Jenny were her breasts. Jenny was a 38D with a small waist and nicely shaped hips. Her ass was round, but not huge; standing at five-seven, her body was an incredibly appealing package.
After I moved in with Jenny, I spent many nights fantasizing about her tits. I jerked off more to one of her bras than I did to any magazine. Once she caught me in the bathroom with one of her bras and my dick in my hand. Jenny just said, "Oh my." And closed the door. Outside the door, she said in a low, sexy voice, "You just finish what you're doing, dinner will be waiting when you're done."
With her approval, I finished. I kept the bra in my room and she never asked about it. It seemed to me that she did wear lower cut tops for a while after that, but maybe that was just what I wanted to see.
When I graduated high school, Jenny and I got drunk and played strip poker. I could not get up from the table when she was down to her bra and panties. I was sure I'd cum right there, but somehow I managed to control myself. Jenny seemed to enjoy it, teasing me, making me wriggle with excitement. She played it up well and when we were all done, she came around the table and kissed me passionately on the mouth. Then she gathered her clothes and went off to bed, leaving her door open.
I gathered up my clothes, stood outside her door watching her brush her hair, and get ready for bed. I wanted to cross that threshold and I think she wanted me to, but I was too far-gone and far too nervous. I shot my load right there when she took off her bra and rubbed her breasts.
Nothing ever happened between us, though I often thought that that's what she wanted from me. We were very close, we were able to talk about everything and I think I worried that if anything happened we wouldn't be so close. But, it was always in the back of my mind and there were days were I still fantasized about her.
So, after failing to find someone that was an ideal partner for the threesome -- someone that Clare would just feel comfortable with -- I decided to get some help from my Aunt Clare. We sat down over dinner one night about two months after the movie and after a few glasses of wine, I decided that was the time to broach the subject with my Aunt.
"You're very worldly." I said to her as I refilled her wine glass. "I'm sure you've experienced things that many people around here haven't."
She smiled wickedly at me, "Such as?"
"Sexually."
Her smile broadened and she shipped her wine. "Well, I'm not a porn star or anything, but I've been around the block as they say."
I didn't know where to go from there I had kind of painted myself into a corner and I felt like I didn't know what to say next. I stammered a little and played with my food trying to remember how I'd planned to approach this.
"Is it something with Clare?" She helped me. "Something wrong in the bedroom?"
"Oh, it's not that something's wrong, it's that I just want to -- eh, try something different."
"Hmmm." She leaned back in her chair her cleavage seemed to push up out of her blouse. "Let me guess, backdoor?"
I laughed a little. Truth was that Clare and I had tried that a time or two and while it wasn't her favorite, it wasn't a problem. "No."
"It's not an oral problem is it?"
"No." Clare wasn't great at giving head, but she was a willing participant. "No, we're okay there." I found myself getting excited with this very open discussion.
Jenny stared at me over the rim of her wine glass. "Are you guys getting kinky or something?"
I laughed again and set my wine glass down. There was only one way to approach this and that was directly. "I'd like -- I'm wondering how one would go about getting into a threesome."
Jenny licked her lips and leaned forward, her breasts pushing against the edge of the table. "Oh, that. Who's idea is this?"
"Mine." I said plainly.
"I figured as much." Jenny's smile never faded. "What are Clare's thoughts on this?"
"Uhm, we haven't really discussed it as far as it actually happening."
"What's that mean?"
"Oh, we talked about it before. You know the typical, 'what do you think' kind of thing and she said she wasn't too crazy about the idea. I guess she had a cousin -- a girl cousin -- who kissed her when she was fourteen and it kind of freaked her out. And then she had a girl at college hit on her so..."
"So, it sounds like you might be two people away from a threesome."
"I don't know." I replied in earnest. "I think she might actually be interested with the right person, but I just don't know how we -- pull it all together, you know?"
The smile never left Jenny's face. "So, you want me to help you figure this out?"
"I just thought you might know how to start this. Tell me what I need to do. You know, how do I initiate it and with who?"
Now Jenny leaned back again and now her smile was more of knowing grin. The wheels were turning. After a moment, she sipped her wine and said, "Well, for starters you need to make sure Clare is interested -- for real. You need to know that when you present this idea that it's going to be fly and not crash."
So, we set a plan in motion where Jenny would find out for me if Clare were interested in a threesome with another woman. Jenny and Clare were friends and Jenny was sure she could find out if there was anything there. Naturally, I didn't tell her that I hoped she would be the third person, I figured one step at a time would get me in the right direction..
