[panhead]

How do start???

I became friends with Lisa 3-4 years ago while she was dating my best friend. They split up but remained friends and we would all see each other socially quite often. She was always very flirtatious especially after a few adult beverages. Well he moved on and got married and she now has a live in as well. Yet our paths always seemed to cross even both of them had moved on. I was out at the mall one night as I had a hall pass for the evening and plans fell through and I ran into Lisa. We decided some drinks and sushi were in order as my plans for the evening had fallen through and neither one of us wanted to head home to our unhappy home lives.
3 bottles of red wine and 2 cabs later we headed home. We both had a great time that night, drinking, joking, b*tching about our significant others, jobs etc. She texted me the next morning to see if the cab got me home OK and we decided we had such a great time we should do it again.
We have become really close friends or something more complicated. Who knows...don't judge me. We get together 2-4 times a month. (More on that later) for our drinking and b*tching sessions. No conversation is off the table. Sex, relationships, work, etc. etc.
One night we were particularly tipsy and she was scanning through some pics on her phone and bang...some incredibly sexy lingerie pics she had sent to her side thing. She didn't try to hide them so I looked...we laughed. I said feel free to forward those any time. And that was the end of it...or so I thought.

Let me describe Lisa. She is late 30's. Very petite about 5 foot nothing. Perfect little spinner body and the most unbelievable little biscuit I have ever seen. Perfect legs, amazing ass and perky gravity defying 32 B's. She is stunningly cute and definitely turns heads wherever we go. She sometimes dresses pretty provocatively when we got out. Skintight jeans, boots, and low cut tops showing off here small but awesome rack. She knows I love down blouse views and she never disappoints. There is no modesty or hang ups between us. Anything goes.

So anyway after seeing the pics she sent to her we call it a night and jump into separate cabs and head home. She typically texts me the whole ride home as mine is a bit longer to make sure I get home alright. I get a text asking if I want to see her pussy. I respond "sure". She sends me a pic of the rescue cat she just adopted. About a minute later my phone vibrates again and she sent a pic from the neck down. Her jeans were off and she was in plain white panties with black lace trim. She had also pulled down her sweater giving me a nice view of her cleavage and plain black bra. I responded “wow very nice”. Moments later another pic, sweater gone…down to her plain black push up bra. She had em really pushed up and out for effect. My reply…”wow that was hot and very unexpected…but I’ve been staring down your shirt all night at that plain black bra…can you step It up a little.

She replies OK…but first you send a pic.
I respond simply, “…of”
She replies well if you want more you gotta show me a little something.
After a few messages back and forth she convinces me to send a dick pic (my first time).
I fluff up a bit and send her a cock pic about half hard. I captioned it with “half mast”.
She replies if I put on my new Victoria’s secret bra and thong will that get you to full mast?
I responded…only one way to find out.
I am in my garage and I crack another beer…no idea where this is heading. A few minutes pass and then a pic arrives.
2 vibrators and the caption…Pick one.
I choose a blue rabbit vibe and then another pic comes over…pink lace bra and panties.
I am completely hard now and she asks did it work. I say yes. She says “prove it”.
I send her a pic of my raging hard on. We banter back and forth exchanging compliments and innuendoes. She sends another pic. Panties off.. her sweet little ass lying on her side. Then another with a bowl of popcorn covering her goodies. Then another close up of her breasts in the lacy bra.
I reply well since we are really doing this and I’ve shown you all I have…will the bra come off too.
She said she was too shy and insecure about her breasts. I assured her they were awesome and we had already crossed so many lines did it really matter.
Seconds later a pic of those perfect little breasts came over. Her nipples were hard and poking. I was hard as fuck. She asked if it did the trick. I said yes. She said show me so yet another dick pic was sent. She said she could see the pre cum and asked if I was turned on.
What do you think? I asked. She asked if I was going to “enjoy her pics” and of course I said yes. She said she would do the same. She attacked herself with the rabbit and I jacked myself into oblivion. OMG I hadn’t cum like that in ages. I shot all over the floor, on the desk it was everywhere. I had a Peter North moment.
When we both recovered we were a little embarrassed and she said OK time for bed we will talk soon.
We joke about that night all the time. When my phone crashed she was even kind enough to resend me the pictures from that night in case I ever needed them.

So that was my first ever sext session with Lisa. We still hang out all the time...things are becoming even more "complicated"