**The actual events took place over about a year or so. I shortened the time frame for this story and remove a bunch of the stuff that did not have a sexual tension. Yes the names have been changed and a few events are the best of my memory. Everything else is close enough.**
How I met Samantha
*Chapter 1
I was introduced to Sam by my good friend Terri. Terri had helped me through some tough times, so to speak, and was always friendly and wanting to help. Terri wasn’t knock out gorgeous she was a petite and slightly pudgy, not fat mind you but she was carried a little extra here and there. Terri has straight brown hair chopped just below the shoulders, brown eyes, nice lips and of course a wonderful rack and booty. She was part Italian and had that natural Mediterranean tan year long. In winter it would lighten up some but in summer after lying out just a few times she would have that deep tanned healthy color to her.
Anyway, Terri felt that I needed to see her friend Samantha or Sam, who was a therapist. I can still remember the day Terri recommend that I should see her, “What, you think I have a screw loose,” I protested.
Terri just gave me a friendly smile, her hefty breasts heaving, “No Dave, just Sam is a specialist who may be able to help you. She is very good at what she does and she has helped a few of my other friends.”
I looked down at myself, and then back up at Terri, “Any of your other friends have my problem,” I sarcastically replied.
“I wish,” Terri started, “no she helps people who have trouble, with…. Well you know…. Sex.”
“Wanna announce it louder,” I protested my voice carrying the indignation that I felt.
Again Terri gave me that pleasant ‘it’s OK’ smile, “No it’s not like that at all, besides I told her about you and she really wants to meet you.”
‘Nice’ I thought thinking of how well that worked for me in the past.
Terri continued, “Look you do not have to see her if you don’t want to, but I think she can really help you. Everything is private, you meet in her office and she will talk with you. Maybe she can help you relax and enjoy yourself some more.”
“Fine,” I proclaimed as Terri handed me Sam’s business card.
“She is expecting you tomorrow at five, it’s after her normal office hours since you’re a special case,” Terri proclaimed.
“A special case,” again I stated with indignation.
At first I really thought about just blowing off the appointment that my ‘friend’ set me up for, but I just could not do that to Terri. As much as I hated seeing a ‘specialist’ I did not want to hurt Terri’s feelings by standing up her friend. I also considered just calling Sam and cancelling, I sure that as a specialist she gets that all of the time. But as one day rolled into the next I ended up not cancelling and it was now hours from the appointment. Fidgeting back and forth I finally went downstairs, hopped into my Jeep and drove to the address provided by Terri. I was glad that I left a few minutes early as the address was difficult to find. I was expecting an office with some sort of sign, ‘Head Shrink Inc.’
On the second lap around the block I found the address and pulled into the parking lot. Stepping out of my Jeep, ah summer no doors, I looked around for Suite B. I soon found it and walked into the building. On the outside of the door was just Sam’s name, no therapy, head shirker, or voodoo witch title or moniker. Discretion was defiantly her forte. The office was cozy with a few plants, some seating and a table with a few magazines but what surprised me the most was the lack of a receptionist. I called out,
“Anyone here?” and was rewarded with a sweet voice, “Be with you in a moment.”
I sat down and decided to peruse the magazines; chick, chick, er nah chick. Ok defiantly not set up for a dude I mean no car, fish, bike or 4x4 magazines, what the hell.
Soon I was rewarded with my first sight of Samantha and I tell you she was one of those gals you just took in. She had curly brown hair that fell in large ringlets, the biggest sparkling brown eyes, framed on a magnificent oval face with a dusting of freckles. She had on a white silk blouse with a black knee length skirt and a nice set of black strappy type heels. Her legs were covered in a nude colored hose and despite her somewhat demure size had a decent pair of tits. She seemed to just glide on those heels as she approached with one of those yellow legal pads in the crook of her left arm and a reassuring smile on her face.
“You must be Dave my five o’clock,” she kindheartedly remarked.
I really don’t remember but I am fairly sure that I replied to her breasts, “Yeh, I’m Dave… You must be Sam, Terri’s friend.”
By this time I knew I was looking at her, because I saw a little crook in her eyebrow as she stated, “Yes I am. Terri has told me so much about you.”
“Really.”
“Yes,” Sam continued, “I knew Terri back in the day and she and I spoke quite a few times. When Terri met you she came to me.”
‘Nice’ I thought, ‘reputation precedes me despite being out of College. I mean I thought I left all that nonsense behind.’
I could only choke out, “Yeah…. Well…. Terri has been very nice to me, helping me along.”
Samantha smiled kindly, “How about we go to my office.”
Her office was a little more inviting than the waiting room with big overstuffed chairs, a sofa that just invited you to plop down and watch some football, and a leather office chair that looked very inviting.
“Who would have guessed a sofa in a shrink’s office,” I retorted.
Sam just continued to smile, “If it makes you feel comfortable, by all means sit of the sofa.”
I did notice the fact she said sit and not lay down. I chose the overstuffed chair nearly directly across from the office chair, which I just assumed must be for her. If I choose to see her again I am going to have to sit in her chair and see what she does. Sam closed the door behind her then glided over to her office chair, my eyes were looking right at her skirt as she sat down, but she was a expert and managed to sit and cross her legs without as much as a free shot.
‘Damn’ I thought, this shrink is really turning me on as I could feel the stirring down below.
“Ahem,” Sam cleared her throat and my eyes moved from the cross of her legs back to her face, “shall we get started, Dave?”
She was wearing a pair of oval glasses as she began to make notes on her yellow pad. I could guess what it said, ‘horn dog looked me over as we entered office then tried to get a peepshow when I sat down. Diagnosis: Deranged pervert!’
“So it seems that you have a little problem,” Sam started.
“Little,” I protested.
That of course led to more jotting in her notepad and a stern look from Sam. ‘OK, not so much for jokes.’
Sam just seemed to continue, “Tell me about your first sexual encounter.”
“My what,” I replied shocked.
“Your first sexual encounter,” Sam stated matter of fact, “You did know that I help people with sexual issues.”
No denying, I knew exactly why Terri sent me to see Sam, it wasn’t because I needed help with my golf swing, which sucked by the way. I merely stammered for a moment, lost in what to say.
“Look,” Samantha stated, “normally I would make you feel all relaxed, get to know you first, make you comfortable with therapy before we would dig in. But, I am doing this on my free time and where I would like to do things normally, I just don’t have the time. I agreed to see you as a favor to Terri, because she cares about you. I have known Terri for a long time, both professionally and as a friend. But, if this is going to work we need to dispense with the foreplay and get right to the heart of the matter. Now we have already wasted five minutes.”
I did not know what to say to this gorgeous woman but I was not lost on the fact that she used the word foreplay.
“What my first masturbation, my first kiss, first time I dry humped,” I asked?
“Sorry,” Sam stated, “let’s start with the first time you were with a woman.”
“Well,” I exclaimed, “I guess my first girl was Kristi.”
Sam replied in a sweet soothing voice, “that’s good and where did you know Kristi from.”
I settled in to tell the story:
Kristi was the sister of my best friend Mike back in junior high and my freshman year of high school. She was maybe a year younger than me and the three of us hug out all of the time. Mike played the trombone, I played the trumpet and Kristi played the saxophone.
Kristi was a dirty blond and maybe a few inches shorter than me. She had blue eyes and a nice round figure. Despite being a year behind me she developed early.
“Did you love Kristi,” Sam asked?
“Back then I would have told you hell ya, but now I think it was more infatuation.”
“So, tell me where you and Kristi decided to have your sexual experience,” Sam soothed.
‘Wow’ I thought, well here it goes:
My family rented a beach house for a few weeks on the Gulf. Since Mike and his family always invited us out on their boat skiing my parents felt it was only right to invite them to the beach house. The house was big enough for two families and everyone agreed, however at the last minute Mike’s parents were unable to attend. I guess rather than punish the kids, they decided to go ahead and let Mike and Kristi come with us. I thought it was great as Mike, Kristi and I really wanted to spend time as friends. We enjoyed ourselves swimming in the ocean playing games, and hanging out. We also watched movies on HBO and MTV in the beach house. There was plenty of room in the beach house but for whatever reason when it came time for bed, Kristi and I snuggled up head to toe on an oversized sofa. Mike would also fall asleep in the recliner about 10’ away or so. We had a big blanket on the sofa and I would pull it over Kristi and me each night.
One morning I woke rather early and Mike moved from the recliner to a pallet on the floor much further away. I guess being a horny teenage male had me thinking with, well not my brain that’s for sure. I decided to flip around behind Kristi as she slept. I snuggled in behind her and laid my arm over her. We were not dating or anything but we were sweet to each other. Any way she was wearing a tee shirt nitie and panties and I cut off sweats and a shirt. It didn’t take much for me to get just a little excited being so close to someone I felt attracted to. Nature taking its course I felt the blood pumping toward my organ and stiffening in my sweats. My hand around Kristi fell just below her breasts. Well I figured what the hell and decided to brush against her wonderful globe and was rewarded with a slight wiggle in Kristi’s butt which was pushing against my lengthening rod. The feeling was ecstatic and when she wiggled her rear and I pushed back slightly to be rewarded with another, firmer wiggle. I could feel my cock peeking over the waistband of my sweats as I continued to rub myself against Kristi’s rear and my hand brushed her wonderful smooth brests. I could hear Kristi’s breathing change pace as we continued to rub and wiggle and I was also soon rewarded with feeling her nipples harden under my hands.
Sam must have been able to tell I was a little uncomfortable as I relived this story, despite my best efforts I was hardening in her office.
“Do we need to take five,” Sam asked.
“No I think I can finish. Is this too much detail,” I asked?
“No you’re doing fine. Whatever detail you are comfortable with providing,” Sam stated.
So I continued the story: I guess sometime in all the rubbing and wiggling I decided to make the move and lower my hand toward her belly. As my hand made its way to her nether regions I felt her push her butt hard into my cock, which was not just peeking through my waistband but sticking out. I took her push against me to be approval and lightly rubbed her mons through her satin panties.
A small moan escaped from her lips and she rolled onto her back. While I was defiantly displeased to no longer have that wonderful ass rubbing against me she also allowed me better access to her crotch. I rubbed her a little more and another soft moan departed her lips. By this point she was peeking her eyes open to dart around the room. Once she seemed satisfied we were alone her hand came to full rest on my cock. She might as well sent electricity straight through me because as soon as Kristi touched me it must have jumped a foot.
I slipped my hand below the waistband of her panties and felt her fuzzy bush as I slowly traced her slit. I was rewarded with her sliding her hand up and down my cock, exploring its length. We continued to rub each other for awhile exchanging a few sweat kisses until my hand drove a little lower along her slit feeling her labia. As soon as I touched her she pushed her mouth hard against me stifling a moan. I gently rubbed and explored her labia with returning strokes back to her slit.
Kristi was definitely breathing harder now, kissing me strongly while her hand pumped my cock. I lowered my sweats to my knees completely freeing my cock for her. Kristi placed both hands on my dick one near my flat belly rubbing the top half and the other closer to my balls rubbing the bottom half.
I slid a finger into her moist tunnel feeling her velvet smoothness. She gasped slightly as I thoroughly enjoyed wiggling my digit inside of her warm flesh. I am not really sure who pushed who but her satin panties came off as we started to explore how to connect our bodies.
Eventually we decided to have her back toward me on the couch as it was better than having someone wake and see me grinding on top of her. I lowered myself behind her and took my throbbing cock and placed it between her legs. Soon the head of my iron hard-on was brushing against her labia and I could feel her wetness urging me in. Feeling her heat and wetness was urging me to just drive into her hard. Yet even then somehow I understood the need to be slow and gentle.
I pressed against her hole and Kristi’s breathing changed, she did not moan but almost seemed to whimper. The purple head of my cock was almost buried in her, but I stopped dead not moving forward as her tightness pushed hard back against my cock.
“Do you want me to stop,” I asked her.
Kristi just shook her head no.
With my cock head buried slightly into her pussy I returned to slowly massaged her slit which seemed to have the effect of relaxing her. Once I felt it was OK I pushed again, and was again she whimpered. My control slightly fading with my head nearly in, I pushed once more and it plowed into her moistness.
My cock was in heaven as it felt like it was being squeezed to death by wet velvet. But, Kristi big beautiful blue eyes were tearing up. I wanted so desperately to start pumping my cock in her and I had allot more cock to feed her. I wanted to feel my balls slapping her has, my cock buried to the hilt in this young woman. But her eyes were telling me this had become for my pleasure only. That was something I could not do.
I held my cock where it was with only my head buried in her and a good portion hanging in the breeze. My hand stroked her cheeks.
I again rubbed her slit and mons with casual brushes against her labia stretched taut from my pole. She seemed to relax again as I looked up at her and was given another nod.
A little more of my cock slipped into her while I was petting her so I pulled back just slightly and rocked forward just a little. This seemed to be OK with her, but clearly it was not enjoyable. More and more I keep trying to give her shallow strokes. Her pussy clamped down hard on the end of my cock.
Finally, losing control I pumped a good few inches into her tightness and she responded with a full yelp.
I looked up and tears were flowing as she shook her head no. I kissed her lightly as I slowly backed out of her wonderful tunnel feeling the drag of her innards the entire way. With just my head left inside I tried to piston again yet she continued to just shake her head no. I realized plowing into Kristi was not going to happen without me tearing to poor girl apart, or at least so I thought.
I slowly pulled my cock head out of her with a muffled pop as her clamp like pussy released my cock. I snuggled back up behind her my cock between her legs between from her rear and out to the front, the middle of my cock resting on her labia and the rest sticking out from her front. I gently kissed her cheeks and even her eyes which were puffy from the tears.
“I’m sorry,” Kristi whispered into my ear, “I had no idea it would be so painful.”
“I, I really want to let you in me,” she promised.
I simply, looked at her lovingly, “That is OK Kristi, I don’t want to hurt you. I can’t feel good if you’re in pain.”
Kristi looked up and me and smiled then kissed me deeply, deeper then we kissed all morning. She peeked around the room again and still happy that we had not woken anyone she peeked under the blanket. I guess her having both hands on my cock was one thing, but to see it sticking out between her legs like that must have been another as she exclaimed, “Oh my Gawd!”
I thought something was wrong, and joined her head under the blanked, “What!”
I thought for sure I was going to see her blood or something, but Kristi exclaimed, “It’s so fucking huge.”
Ok so this is the point I am suppose to feel like a man, say ‘yeah baby damn right, it’s a two handed monster.’ But, nope I just felt so ashamed that my dick had hurt Kristi so bad.
“Sorry,” was all I could say.
She just looked back at me and kissed me deeply again as I could feel her legs start to move just so slightly and her labia rub on my dick. I got an idea and pumped my dick between her legs from her wonderful ass toward her cunt and back again, allowing her labia to ride against my dick. It was not my dick in her pussy, but it felt so damn good. I reached down to her mons again and slid my finger up and down her slit. A few well placed rubs had her moaning again as she took my finger and moved it on top a hard bud near her labia. Her clit as she whispered into my ear, “rub it gently right there.”
Kristi then grabbed the part of my cock peeking between the front of her legs and started to stroke my cock. It did not take long flicking her clit for her to get all wet again and soon she was leaving a sloppy trail of juice on my cock. However, the top half that she was stroking was dry. I pulled my dick back far and slopped the top half with her juices before sliding back forward again. Kristi just looked shocked as I continued to stroke my cock between her legs and fiddled with her clit.
“Stroke it,” I moaned.
Watch out for part two
