This is going back MANY years. I was 24 (m) and engaged and still a virgin. My fiancee was a virgin too — it’s not like we were saving ourselves until we were married; my fiancee was just very uptight. And so… I waited.
But I had a female co-worker named Judy who was a about 11 years older than me – and we were REALLY great friends. We got along really well, enjoyed each other’s company, laughed, had fun, worked really well together. She was great. She was also stacked. Like SO stacked. I used to catch myself staring at her tits constantly.
Anyway…we worked together really closely, very long hours, very late nights, and I developed a huge crush on her but never did anything about it or said anything about it. Our job required some frequent travel, and this once time, we had to go on a business trip to Chicago with a team of about 8-10 other people. So we were all staying in the same hotel and at night or during down time, we’d hang out in each other’s rooms watching movies, ordering ridiculous amounts of room service on the client’s dime and having as good a time as we could given the long hours we had to work.
This one night, we were watching movies in Judy’s room and the couple of others in our group who were with us said they were tired and left, so it was just me and Judy. So we were laying on her bed on our stomachs (fulled clothed, on top of the covers, nothing remotely sexual about it), watching “A Fish Called Wanda” and snacking on something — and I leaned in towards her so our shoulders and arms were touching. After a little while, I turned and looks at her and she turned her face towards mine — and I just leaned in a kissed her. It was amazing. “Patrick!”, she said – the surprise on her face that I’d kissed her was apparent. I asked her “Is it OK that I did that?” and to might surprise she said “Oh hell yes!! But not lying on our stomachs like this! Come here!” and she rolled over on her back and motioned for me to move over to her. We kissed and again and it was incredible — he was a great kisser and I was so into her.
We kissed for a bit and my hands roamed from her waist, up over her shirt to her huge tits. She stopped kissing me for a second and said “What do you want me to do?” Now keep in mind, I was still a virgin and nervous as hell…so I said “Take off your shirt”. And she didn’t hesitate — off came her shirt revealing her massive tits being restrained by her bra. I was playing in my head how cool I would have to be about getting her bra off her, but I didn’t even have to. As soon as the shirt came off, she said “And let me get rid of this tired old thing too” and took off her bra too, revealing the most incredible DDs I have ever seen.
We started kissing again, with my hands now all over her chest – cupping her tits, playing with her nipples. I could tell from her reaction that she loved having her nipples played with and I was thrilled to finally have the chance.
We rolled over so I was on my back and now and she was half next to me and half on top of me, kissing me….and I took her hand in mine and started to move her hand down to my crotch. And she stopped me. I thought “Damn – I’ve gone too far”. But I was wrong. She only stopped me to ask “Do you really want me to touch you there? REALLY want me to?” And I was like YES! Hell yes I do. And I expected her to start touching my cock thru my pants, but instead she said “OK, then let;s do this the right way” and then unbuckled my belt, unzipped my fly and pulled my pants and underwear down and off before I knew what was happening. And then she went down on my cock and took me into her mouth. Which was the first time that had ever happened to me. It’s still embarrassing to say, but being inexperienced and a virgin with an uptight fiancee meant this was my first blowjob ever — and it was incredible. She was SO masterful with my cock, I couldn’t believe it! She could tell how close I was getting and in between licking and sucking me off, I heard her say “I want you to cum in my mouth” which was all I needed to hear. I exploded in her mouth and could hear from her moans that she loved that I did.
After she finished, she came up and laid next to me and saw the look on shock on my face and asked what was the matter – and I said “Nothing! That was incredible. It’s just that…. well, that’s the first time that’s ever happened to me.” And she was like “Wait – you never had a blowjob before?!” And I said “Until now, I’ve never had ANYTHING before, let alone a blowjob.” And she was dumbfounded. She paused a second, letting that sink in, and then she got up from the bed, topless but still wearing the jeans she hadn’t had time to take off yet, and she pulled her jeans down, stepped out of them and stood before me naked and looking incredible and said “Well then, get ready for some more firsts!”
She climbed back on the bed and on top of me and we had our naked bodies pressed together for the first time — amazing. Then she said “Well, given how much you just came, you are going to need some time to recharge. Are you up for something else — for ME?” and I said “Hell yes – I will do whatever you want!” She she rolled off me and was laying next to me and said “Good, then come here and let your hands do some exploring. Her big tits looked so incredible, but that wasn’t where I wanted to explore. Her big tits looked so perfect and amazing — and as I started to kiss them and suck on her incredible nipples, I let me hands start on them and then slowly work their way down her stomach and between her legs. She was dripping wet already and she parted her legs to let me go to work –first rubbing and playing with her clit. Her back arched and she moaned and writhed as I slid one finger in.. and then two. Finger fucking her was more than I could have imagined would happen that night, but it was just the start.
After a little bit, I slowly moved my mouth from her beautiful tits, kissing my way down her body, stopping to spend a few seconds at her belly button while still fingering her wet pussy. And then I continued to move down until my face was between her legs — it was really the first good look I had gotten. Her nicely trimmed bush and her full, wet pussy lips looked so inviting as I slid out my fingers. — I looked up to make eye contact with Judy and she had the biggest smile on as I went down on her. I know I didn’t really know what I was doing — this was the first time for this for me too, but it was amazing! And her groans and movements let me know when I was on the right track. She bucked and writhed on the bed as I licked and nibbled her clit. When I added a finger back in and started fingering her while I eat her pussy, that proved to be more than she could hold back — her body stiffened and her thighs clamped around my head as she came and let out a huge scream. (She later told me that her orgasm made her so lightheaded, she thought she was going to pass out!).
After she came, I moved myself back up to kiss her… the faint taste of my cum was still in her mouth from earlier. After a few minutes, she caught her breath and then asked me again: “Were you serious that you have never had sex before?” and I told her again that I was was. “I know, it’s embarrassing at my age, but yeah, I’m still a virgin.” Then she looked down and saw that my cock was back to fully hard again and she replied “Well then, not for long”. She grabbed a few pillows and propped them up and told me to sit up with my back against the headboard. “I want to make your first time perfect”, she said. “It already is”, I told her, but I knew it was about to get even more perfect. She kissed me again — long and hard, and she gently stroked my face, then ran her hand down my hairy chest and gently took my hard cock back in her hand. The she climbed on top of me so we were face to face, cowgirl style….still kissing, still fondling my aching cock. And then she moved closer to me, and with my cock in her hand she rubbed its head on her clit and across her wet pussy lips….teasing me. I was so close to being inside her, but she teased it for what seemed like forever. She had stopped kissing me at this point — I think she wanted to see my face and see what this teasing was doing to me. And actually, I think she really wanted to see what my face looked like the first time I was inside a woman. Because when she finally pushed my cock head inside her and sat down on it, the joy in her face from seeing what she was doing to me was apparent. My God…. the feeling of my cock sliding into her and finally being inside her was incredible!
She as slow at first — she wanted this experience to be perfect for me. She rode me for what seemed to be forever. Sometimes we kissed — sometimes she moved her upper body away from me so I could watch her ride me. God, her tits looked incredible as she rode up and down on my cock. After a while, so asked “Do you want to try something different, her can I make you cum now?” I was so ready to cum, but I didn’t want this to end, so I said “Well…. can I get behind you?” and her face lit UP! “Hell yes,” she said, “I love that!” And with that she slid my hard cock out of her. climbed off, and instructed me to stand next to the bed. She positioned herself kneeling away from me, her long blonde hair cascading down her back. When she went down on all fours, her long hair slid off her shoulders, and hung down next to her boobs which looked incredible like this! But even more incredible was the way her ass and wet pussy looked — so inviting! So I moved up behind her and she reached back, took my hard cock in her hand again and slowly, gently guided me inside her again. Oh my God… the feeling of sliding in and out of her was completely different than when she rode me cowgirl style, and I wasn’t prepared for how much the visual was going to affect me too, because almost instantly I was about ready to explode. So I started trying to think about other things to distract me so I could at least last a little longer. It work – but only briefly. The feeling of sliding in and out of her warm, wet pussy, the visual of her big tits swinging, the visual of my cock going in and out of her and the sight of her beautiful ass was really more than this virgin could take. “Don’t worry, I’ll pull out” I told her — and she said “Don’t! Please! Fuck me harder — cum IN me!” And I could see on her face in the mirror that she meant it. So I grabbed a firmer hold of her hips and started pounding her harder — my thighs slapping against her ass, her big tits swinging like crazy until I could hold off any more. As I felt myself ready to cum, I pulled her hips in hard so I was as deep as I could possibly get and I exploded inside her. It was nothing short of amazing – the best orgasm I have ever experienced!
We collapsed on the bed and laid in each others arms, totally spent. She made my first time so incredible – it was a night I will never forget. We fucked a few more times during that business trip and some more in the weeks and months that followed (back at home and on subsequent business trips). She was my first and I will never forget how perfect she made it.
Source: reddit.com/r/sexystories/comments/sina1z/virginity_lost_to_a_coworker
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What happened with you and the fiance?