Ch. 01: Several Firsts with a Friend

I'd like to share some stories. I've had some interesting experiences that are much too sensitive to easily share; so I've bottled them up for years and years. I'll start with my very first sexual experience and progress through a history of unique encounters.

Firstly though, every detail is absolutely authentic and factual. Second, certain details have been left out to protect identities, especially of the women in these stories who aren't aware I'm sharing them.

I'll take you through my first, which was actually several firsts in one, then go over my wonderful first experience through the world of online hook ups, and finish up with a story of how perfectly great sex can be ruined by what happens afterward. I hope you enjoy.

I was about 19 and shy... really shy. That shyness was oddly enough part of the reason I was so horny. I know, 19 year old guys are always horny. But you have to understand I was on another level. You see, not only was I a virgin but I hadn't even kissed a girl. So there I was, a sad little 19 year old with a tent pole in his pocket 24 hours a day.

I was at a party having a good old time. I'd met some new people and chatted with old friends. One new person was a woman who happened to be a friend of a friend... of a friend. So yeah, very distant in degrees of friendship to say the least. We chatted and she was very nice but I wasn't likely to see her ever again. Not only were we separated by our line of mutual friends but also age. She was 30 years older than me. If you're doing the math in your head, she was 49. Anyway, we went our separate ways and that was that. Or so I thought.

As it would turn out, the world is pretty small and we kept running into each other. Sometimes it was at a party, sometimes at a restaurant, you just never knew. And I'm not talking about bumping into each other a few times in a few months. I'm saying I probably saw her monthly for a span of almost three years. We actually got to know each other and got along very well. We would talk about all kinds of things including my shyness and lack of a girlfriend. We'd bump into each other at the bar once I turned 21, have some drinks and have a good old time. We even exchanged phone numbers and hung out together, just the two of us.

One day, she calls me and asks if I want to hang out. I was headed to the gym and wanted to stick to the plan. She understood and asked if she could join. I saw no issue and had her meet me. I was allowed one guest so she got in with me and we started doing some cardio and chatting. It was late, maybe 9:00 PM. The room was dark and so was the outside world barely visible through the glass store front.

We were on the stair climbers chugging away at a leisurely pace when we got onto one of our typical subjects which was my love life or lack there of and that's when she surprised me.

She told me how she understood how I felt and that she wanted to be that person I needed. My head began spinning. I tried to gather my thoughts and figure out where I'd go with this. I'd never really thought of her that way. It's not that I didn't find her attractive or was afraid of an older woman. In fact, most of the porn I was watching at that time was of older women and younger guys. I just hadn't considered such a possibility; that even though girls weren't interested in me, a woman would be. Plus she was married with kids my age. I actually knew them well.

So I gathered myself and explained that I too felt some connection but I knew she was married with a family. She went on to explain how loveless (and sexless) her life was and that she needed a companion the way I did. I knew what I was considering with this 51/52 year old woman was wrong but I was 21 and had never had a kiss. How many guys would say no in that situation?

She went on to explain that we were friends and truly cared about each other, and that there was nothing wrong with two friends who care for one another, taking care of each other's needs. With that, I willingly took the bait. I asked how it would work and she said we could get a room somewhere. I asked when. Her reply, "right now."

All I could say was "ok, let's go."

We walked outside and stood between our cars. She came in to hug me and with that, we somewhat awkwardly but sweetly shared our first kiss... my first kiss.

I said I thought I knew a place and told her where it was. She knew exactly where I meant. We drove separately, me as fast as I could.

When we arrived, we walked into the office together. I asked for a room with two beds as if that was going to fool anyone. We went into the room, sat down on the beds and began holding and kissing each other. My hands went to the curves of her hips and her arms wrapped around me.

Still with our tongues entwined, we slowly laid back onto the bed, she on her back, I on my side. One of my hands worked upward until I reached one of those soft peaks. They were big and for the first time, I held a tit in the palm of my hand. I massaged her slowly as our tongues flicked and danced; mine trying to mimic the movements of hers. I wondered what more I should do with my hand.

She began to pull off my shirt and so I slid out from it and did the same to her. Next I anxiously went to the rear of her bra. Having seen plenty of scenes in comedies that started this way, I filled with nerves as I reached back behind her, but I had no trouble unclasping each of the four hooks one by one.

Her tits were amazing. They were big and they were mine for at least the next few minutes (hopefully more). We quickly got out of our pants and laid backed together, me staring at the fullness of her chest, and the dark Ariel as crown by large but feminine pink nipples. We continued kissing as I didn't want to rush. I'd heard women don't like to rush. Then I heard it, "I want you."

That's when I rolled over and nothing. I went limp. Here I was ready to lose my v-card with a curvaceous cougar who was ready to go and I had nothing. I could feel myself shaking and I knew right away it was my nerves. That's when her instincts kicked in. She kissed me some more and used her hand to massage my shaft but after years of 'putting the pussy on a pedestal' I couldn't shake the nerves. She used her lips and tongue to expertly try to awaken me and still nothing. So she removed all the pressure. "It's ok, we can just talk and try later." That's just what we did. We talked in the room and hung out but later was not in the cards for me that night and after a while we decided to dress and head home.

She texted me the next day and told me she had a good time and thanked me for the time we shared and for getting the room. I figured she was just that sweet.

A few awkward days passed though and she reached out again. She wanted to see me and hang out, no pressure. So we decided to go for a drive. She left her place and I picked her up at a spot we'd selected not far. From there we just drove and talked. Of course there was an elephant in the room, or car. So she attacked it with such grace it was amazing and I was powerless.

She told me that she would love to just park and make out somewhere, like a couple of teenagers, and that's precisely what we did. But one thing leads to another as they say, and we somehow migrated to the trunk of my SUV, rear seats down, windows fogged, parked along the curb of a residential neighborhood. I was on my back and she straddled me on her feet, leaning forward hard to bring her jeans to her knees but it wasn't enough space. Try as we might, it wasn't working. It was just too cramped. I don't know who made the suggestion but one of us noticed the woods nearby and suggested we walk the path and find a quiet spot.

Up her jeans went and out we ventured. We walked the path a bit until we found a spot that wasn't private at all but private enough for us in that moment. Again she leaned forward and pulled her jeans and panties down, this time removing her left shoe and stepping out of the left leg. She left the jeans clinging around her right ankle and foot with the shoe still on. Then she laid back in the dirt as I dropped my shorts and boxers to my knees. With a view of the nearby houses, I split her knees around my waist, looked down at her soft, mountainous breasts under her white T-shirt, then made eye contact and plunged my turgid virgin cock half way in.

There was no foreplay, no love shared, no kissing in that moment. Just animal lust.

I slowly lowered myself further until my full length was encased within her. An electrical charge was passed back and forth between us going out and returning simultaneously from our connection like a plug in an outlet. I drew back for the first time and eagerly pressed back in.

Slowly we built our rhythm as her head rolled back and a soft sigh escaped her breath. It was an outward sing of both the gratification and relief we each felt in that moment. I began to give her myself a little bit faster. A slight squeak came out between her lips. I leaned in and pressed my lips, splitting hers and slipping my tongue in as I began to actually fuck the sweet cougar beneath me. Her leg flailed upward to give me the leverage needed to delve deeper.

I looked down at the sight below me and she upward. Our eyes met again and unspoken words were communicated. Thrusting and pumping I continued to press hoping no one approached on the path or looked out the nearby windows, to interrupt our pleasure. Her hands were on my back and I felt the sensations begin to overwhelm me. My balls slapped against her ass all the while becoming a a pair of boiling cauldrons.

"Im going to cum," I said. Her voiced softly whispered her gentle response, "yeah?"

"Mmhmm," was all the response I managed at first. "Where should I do it?" I nervously asked. Confidently and knowingly she told me, "inside me."

I responded, "are you su..." it's a good thing she gave me a feverish nod as she said, "oh yes," and her legs wrapped around my waist and back to pull me in, because I didn't even get the question out as I boiled over and began to explode, still thrusting as I filled her wet milf pussy with my young seed. Bolt after bolt fired out and my cock pulsed until my full load was deposited within her womb. I pressed to the hilt to push it all in and savor the sensation. We kissed and laughed together. It had finally happened and in our own unique way, with our own unique connection. I sat only for a moment as we caught our breath, having finally consummated our special friendship properly.

Finally we untangled our body's and got our clothes which were only half off back on. The back of her T-shirt was covered in dry leaves and a light dusting of dirt. She assured me it wouldn't be an issue.

We decided to finish walking and talked for almost another hour in those woods encountering a pair of strangers walking toward our "secret" spot. This was just moments after we'd left it and we pressed on along the trail for a good while after the encounter and before returning to the car. I drove her back to where I'd picked her up and I dropped her off. I felt amazing and over the moon about what had happened but felt bad because I wasn't sure she had orgasmed (years of experience later, I know she didn't but I suspect she did finish the deed on her own to better effect then normal).

The next day she called me to tell me how wonderful it was. She said the feeling of sneaking in, dirt covering the back of her shirt and ass, with cum dripping into her panties had drove her wild. She asked when we could do it again and I eagerly replied that I wanted to as soon as possible. She explained that she wanted our next shared experience to be special, comfortable, and not so rushed. She wanted to get a nice hotel room and spend real time together. Over the next few days we picked a date, hotel and talked fantasies. When the date came, I was told a time and room number. She's insisted on treating and after much disagreement I had to give way. I arrived and knocked on the door. She slowly opened the door hiding behind it just peaking out. I stepped in and silently closed it. There she stood in a short dress, black stockings and red peep toe heels with ribbons on top. Despite my inexperience I could tell it was she who was actually more nervous for the first time, so I took control. She actually felt self conscious and exposed with all the effort she put into her appearance, but she looked like a goddess to me.

I pressed her to the wall and passionately entwined our tongues. My hands went wild over her body. We stood there, her back against the wall kissing for minutes. I kissed down her neck, chest and belly. I pressed a hand on her midsection to steady her while I lifted one of her legs to place my head between her thick thighs and plant kisses over her pelvis.

I noticed she had less hair than before. She told me she had gotten a waxing right after we had made our plans to meet and she hoped I liked it. I did and was thankful she didn't go all out and had left a patch of well trimmed hair above her pussy.

I pressed my lips and softly laid my tongue over her slit then ran it up. Her balance wavered and she suggested we move to the bed.

On the bed we undressed each other (she kept the stockings and heels on which she knew I liked) and pulled out a bag. In it were some toys and some odd things like whip cream. She said she wanted to eat the whip cream off me and that she'd never tried it but always wanted to. She laid me back and placed a small line of aerosol whip cream over me, leading to my erect cock. Then she began kissing my skin and inching toward the line. She lapped at the cool white cream turning the skin beneath warm. She sucked at it and kissed it off, inching closer to the rod between my legs until finally she reached it. She placed a drop on the head then engulfed my length. She bobbed up and down expertly. She continued and as the pleasure mounted I wanted to return the favor before I went over the edge. I placed her on her back and returned with the whip cream, making sure to dot her nipples also. After teasing minutes spent all over her body I lapped at her taut nipples and worked down to her pussy where I slipped the tip of my tongue between her folds and worked up to a full lapping until she began to squirm and I knew she was ready for me to move up to her clit. It took a moment but I located a woman's clit for the first time and placed my eager lips over it, sucking it in, gently at first, then harder. Using my lips and drawing her in. "Please," she said, "I need you." Again for the second time in a week I hovered over her and placed my cock against her pussy. She grabbed for it and lined me up and slowly I slid myself forward. I even teased her by only giving her a little and she begged and bucked up at me. We began to press ourselves together, encouraging one another to go on, to go harder, and to go faster... and fucked like this for some time until she said she wanted me from behind. She stood at the hotel room desk and leaned forward facing the closed window. I stood behind her and held her wide hips as I thrust in. We fucked like animals. Grunting and pawing, clinging and slamming our bodies together looking out over the parking lot through the glass wall. The light of the room seem to flicker as the desk lamp rocked back and forth, clinging on for balance.

After that we returned to the bed where she rode me long and more slowly until I came inside her. We laid together in sexual bliss. The room was warm, the bed wet, and our heads spinning in the afterglow. We were sweating and saturated in post orgasmic ecstasy.

After about a half hour of petting, light play and talking, we showered together.