Carolyn – My First

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“Oh my God, Carolyn!!” was all I got out of mouth before the cum started squirting out of me. Carolyn just sucked and sucked and swallowed me down. I have never felt anything like it. I groaned. I grunted. I hissed. I got dizzy. My first ever blow job.

I had been working at a local store, part of a major retail clothing chain. I loved my coworkers. We had a great team. In spite of the age differences and personalities, we always had a good time. We often ate lunch together and would occasionally all go out together as a team. I’m still friends with some of them 25 years later.

Carolyn was one of those coworkers. She was short and thin with poodle curl hair and glasses. She was kind of quiet and not all that attractive but was very sweet. She was in her forties and smoked. I think sometimes she didn’t know what to think of some of us younger folks. I’m sure we seemed goofy.

I was 18 at the time. I was lanky and skinny. I would laugh, joke and cut up like crazy. I was an extreme extrovert, until it came to girls, then I was shy. And yes, I was still very much a virgin. I was straight. I LOVED girls and women. God only knows how much I jacked off back then. But when it came to talking to them and asking them out, I was a freakin’ ZERO. That all changed when Carolyn got her hands on me.

It all started when Carolyn started coming to work in really bad moods. She wouldn’t talk much and some of us saw her crying quietly here and there. One day I got up the nerve and asked while we were the only 2 in the break room. Her answer was crazy. It turns out her husband was not only having an affair, but he was fucking one of their daughter’s friends from college. Damn. Carolyn broke down and started to cry as she talked. She started to walk off ashamed but I grabbed her and put my arms around her. It was nothing sexual in any way. I was just comforting my friend. I just held her for a few moments and let her cry. After she had calmed down, we both went back to work. That evening around 10 PM as we were leaving, Carolyn called me over to her car.

“Thank you for your friendship today. You don’t know what that meant to me, John.” She said as she put her stuff in her car.

“It’s what friends do. Hang in there, OK? You have a lot of people who love and care for you. We’re here.” I responded.

“Wait” she said and she wrapped me up in a hug, “You’re a sweetheart.”

Then we started kissing each other and ended up getting it on in the car, right? Wrong. Neither one of us made a move. It was just friendship. I’ll admit that I got a little turned on when she hugged me but I didn’t act on it. She was after all, a friend and she was going through something awful. Only a jerk would take advantage of that.

A couple days later, Carolyn and I worked together again along with another female coworker. It was a pitifully slow night. We ended up unboxin and pricing a bunch of stuff to put out. While we were working, our asst manager, Paula, started complaining about her back and shoulders so I rubbed them for her. I’d done it many times. It wasn’t really flirtatious or anything. After all, I was as backward and shy as they came back then. After a few minutes, Paula told Carolyn that she needed to let me do her shoulders and back, too. Carolyn responded that she’d never had a man massage her like that. So I stopped Ankara travesti rubbing Paula’s shoulders and started on Carolyn’s. I started with her skinny little neck, massaging it deep with 2 fingers on either side and worked my way down to her shoulders, working her muscles deeply and sensually.

“Oh wow, that is incredible, John.” Carolyn moaned, “I can’t believe the girls your age aren’t chasing you with talented hands like that.”

“That’s because John don’t know what to do with them, Carolyn.” Paula chided as she walked away, “I bet he’s never had any.”

“That’s OK” I responded, “we’ll see who doesn’t get any more shoulder rubs.”

As she walked away I blushed deeply. But, she was right. I kept kneading Carolyn’s shoulders then started down her back. As I got down to her lower back, Carolyn grabbed my hands softly and pulled then around her and leaned back into me.

“Hold me again, John, please.” She cooed. So I held her from behind and gently rocked her in my arms. Only this time it was different. I noticed the warmth and femininity of her small framed, mature body. We were sensual this time. I got hard almost instantly. I tried not to but I just couldn’t stop it. She felt it. She looked up at me and said that it was OK. We held that gaze for a moment and then it happened. We kissed. I had kissed girls before but this was different. This just happened. It was soft and sweet and passionate. It was as natural as breathing. I could feel the passion between us. It was so different than kissing the few girls I had dated in high school. At that age, chemistry was something I needed 3 credits in to get a college degree. I had no idea that Carolyn was about to show what chemistry between a man and woman could be. We soon broke the kiss at the sound of Paula shutting the back room door. Our private moment was over for now. I went back to rubbing her shoulders as if nothing had happened. Once Paula joined us, she said we needed to clean everything up and get ready to close for the night. She stayed up front while Carolyn and I carried the totes back to the back room. After we put them up, we kissed again. This time it was more hungry and feverish. We wanted each other bad. Me, the 18 year old geeky virgin and her the recently gilded wife. We both had a need and the other one could fulfill it.

After kissing for several minutes, she stopped me. Then she got down on her knees in front of me and undid my zipper.

“I want to be the first woman to taste you, John. Please let me do this.” Then she pulled out my cock and looked at it. “You really do want me don’t you?” she asked.

“Yes, Carolyn, please…” I begged.

Then she slowly slid my cock between her lips, engulfing it with her mouth. She didn’t go quickly. She was slow and thorough. She was tasting and savoring me. The sensation was incredible. I wish I could say I lasted then fucked her on the break room table but I didn’t. Now, back to the beginning of the story once again.

“Oh my God, Carolyn!!” was all I got out of mouth before the cum started squirting out of me. Carolyn just slowly sucked and sucked and swallowed me down. I must have shot 3 or 4 times hard before the rest dribbled out of me. She never missed a drop. She hummed and moaned and she took my hardness and my hot cum into her mouth.

“Thank you, Konya travesti John, I really wanted to be the first to give you that. And damn, you tasted good.” She cooed.

Wow was all I could respond with. I was out of breath, dazed, dizzy, and amazed.

“Thank you.” I huffed. “That was incredible.”

“Now, when we get off tonight, I want you to leave then come back in about 15 minutes after Paula leaves. I’ll be parked behind the store. We’re not done yet, young man.” Then she kissed me again. I decided right then and there I don’t mind the taste of my own cum as long as it’s from a woman’s mouth.

“OK.” I said, knowing what she meant. I started getting hard again right then.

So after we got everything ready, we all left. I followed Paula to the bank to make the deposit then circled around and came back to the store. Carolyn was waiting behind the store in her mini-van. I parked in front and walked back there. I walked up and sat down. We began kissing again. We stopped kissing while she backed her van back to the loading dock. It would be hard for anyone to see us back here. Then we climbed into the back and resumed our passion.

“John, I’m fixed so you can’t get me pregnant, OK? No worries there at all.” she told me.

“So you want to uh? OK.” I stumbled.

“Yes, I need you, John, please don’t be shy or hold back,” Carolyn reassured me, “I want you IN me, baby boy. Don’t worry, I’ll teach you what you need to know.”

With that, she took her blouse off over her head. I removed my tie and started undoing my shirt. Then we were skin on skin. I had only felt this once before, when I was dating girl and we kissed at her family’s pool. I had chickened out that time. Tonight was going to be different though. I undid her bra and pulled it off of her. She had small breasts. They were soft and a little saggy but her nipples were like little bullets jutting out. I pulled her tight against me as we kissed deeper and heavier. Suddenly she broke the kiss and pushed me downward. I took the queue and worked my down her chest and one by one, I took those hard nips in my mouth and sucked and licked them like a hungry puppy.

“Bite them, John” she hissed, almost in an angry voice. I did. Even at that inexperienced age, there was one thing I did know, listen to the woman. “Oh my God, yes, just like that!” she cried, “So good…so good.” At that point I reached down to touch her pussy and realized she had no panties on. She had removed them before I’d gotten there. I slipped 2 fingers inside her and kept up with the licking, sucking, and biting of her nips. Carolyn came hard. I’d seen girls get excited but not like this. “Oh fuck don’t stop!” she ordered and I obeyed like a trooper. After making some crazy noises, she went limp, breathing heavy. I slid up next to her and held her. She cuddled up like a little girl against me.

“That was so good, thank you,” She whispered, “just hold me like this for a few minutes baby then you can have me.”

“Can’t wait,” I said.

With that she reached down and felt my cock. I was hard and ready to go. We kissed lightly as we snuggled. I touched and caressed her everywhere. I had never seen her in this way before but at this moment, she was the most beautiful woman alive. I wanted to experience every part of her. After a few minutes, İzmir travesti she kissed me deeply again swirling her tongue with mine and running her hands through my hair pulling me close. She pushed me back a little and bent down and started sucking my cock a little bit. Then she leaned back and pulled me over toward her. Her legs were spread wide and her skirt was pulled up. She looked at me with a loving but hungry face.

“Take me baby boy, I need it so bad,” she said as she pulled me into her. Just as we started to kiss, my cock head touched her labia. We both moaned at the feel of our first contact. I found her opening and began to push in slowly. Her spit on my cock and her vaginal juice did their job. I slipped inside her and began working my way all the way in.

“Oh Carolyn, that feels SO good,” I stammered as I slid in and out of her, relishing the sensations.

“Yes, baby boy,” she whimpered, “take me, I’m all yours.”

With that I started sliding in and out of her and a slow pace, kissing her and holding on to the back of her van seat to steady myself. As I took it all in, the feel of our bodies merging, the sound of our sex, her perfume mixing with the scent of her sopping pussy, her moans, it was amazing. I was having sex with a nice looking, passionate, older lady. Looking back, I’m glad it was her and not some goofy ass girl who would have been as awkward as I was.

“Harder John,” she demanded of me, “I won’t break.” So I started fucking her harder. It felt amazing. Every time I pushed all the way in, I felt like I was hitting something in the back. I’m only 6 and ½ inches long but apparently that was more than Carolyn needed.

“Yeah! Just like that. Feels so good. Fuck me, John!” she coached. And I did. After a few minutes, I have no idea how long, but Carolyn started to cum again.

“Oh God, YES!! I’m cumming John. Ahhhhh! Ahhhh! Oh yeah! Oh yeah! YES!!” she screamed in a high pitch as I just kept fucking her like a machine. I could feel your vaginal muscles going crazy inside and it set my 18 year old cock off.

“I’m cumming Carolyn!! I’m cumming in you!” I replied as I started squirting her pussy full. It was incredible to say the least. Carolyn ended up cumming twice once right before I came and once right afterward. It was intense to say the least. Her last orgasm felt like it was pushing me out as I started to go limp.

That was our first time together but not our last. Carolyn’s husband left and I got invited over a lot that summer. I fucked her every chance I got. She taught me so much about women, sex, and love. I gave her massages and attention and just accepted her. I found out later that her hubby had been abusive and cheated a lot. I didn’t understand that and I still don’t today. Why would a man not be good to a woman like that? I treated her good and she let me do anything I wanted to her. I never ever hit her but I did spank that ass a few times, which she loved. I almost wonder if her husband cheated on her because he couldn’t handle her sexuality or was afraid of it. Who knows?

We managed to keep things secret for the most part at work. Paula figured it out but she never told anyone. About a year later, corporate moved Paula and I to another store. She and I ended up talking one night and the subject came up. We ended up sleeping together and then dating for several months. That’s a whole other story for another day though.

So Carolyn, if you ever read this. Thank you sincerely. You have no idea how you helped this shy, goofy kid become a man. And according to most of the women I’ve been with, you taught me well.

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