Yesterday morning, when we just woke up and cuddled, she basically jumped me - we pulled each other's clothes off, started to seriously make love to each other. When I first reached down to play with her pussy (that she had just completely shaven the day before), I felt that she was sooo wet and smooth - I couldn't wait to slide into her, and we started making passionate love.
After a couple of minutes, with a very naughty look in her eye, she said "Make me cum with your mouth..." - she loves oral, especially when I suck her clit as hard as I can. This was music to my ears, and I went down on her. The juices were literally flowing out of her, and - as I had sometimes done before - I started to gently play around her anus with my fingers. I have always been very careful not to go too far, but this time, I ended up fingering both her holes while sucking her clit for a short while.
The fun part was, when I stopped, she asked me not to... "Don't stop, do it again....". I got some lubricant out of the cupboard, and proceeded to very intensely pleasure both her holes. With her still on her back, I slipped my dick back into her pussy (man, that felt so good, it was not difficult imagining my fantasy of another man having fucked her already) while playing with my finger in her rear.
It was fun discussing our fantasies... I asked her whether, in her threesome fantasy, both men are in her pussy, or whether one was in front and one behind. She answered to the latter. I then took the chance of asking whether, if I was really gentle, she's like to try me in the rear. She immediately answered "Yes!". I couldn't believe I was finally going to see what this was like.
Problem was, with her on her back, and with me literally "over-aroused" - I battled to get into her rear, she was also not fully relaxed yet - and everything was COVERED in lubricant. We changed to a doggystyle position, but I was back in her pussy while fingering her behind.
After a couple of minutes, I felt the time was right... I was rock rock hard, and I had worked a lot of lubricant into her anus. I slipped in... slowly at first. I loved the initial tightness, but she proceeded to relax a lot, and I could fuck her in earnest. I couldn't believe this was happening, we were both so turned on.
I particularly enjoyed reaching around and putting my fingers in her pussy, I could feel my own dick sliding into and out of her from the inside. I can just imagine how hot it must be to feel another man this way, i.e. for her to be completely filled up. It was incredibly sexy to talk about this during our lovemaking. After about 5 minutes of hard fucking, I came in her ass (quite a volume!) while she was fingering herself...
After that (which caused several orgasms for her so far) she still asked me to go down on her again! We were absolutely exhausted after this, but what an experience. My conclusions were:
- A double-penetration threesome must feel freaking awesome
- Anal sex was interesting, but by no means preferably to what her pussy feels inside. Even after this (and now knowing she's open to this) I much, much prefer the more complex, interactive insides of the vagina. It just feels so much more "connected" and intense than the anus, which clearly has not been designed by evolution to stimulate the penis in the same way.