*This is a true story. Except for the names, all details are true*
Jean is an ex colleague whom I’ve known for more than 10 years. She was my colleague when I was at my first job, when we were both in our late 20s. She was one of the hotties in the office, but because I was attached at that time, we were just friends. Unknown to her, I sometimes fantasized sexually about her, and unknown to me, she secretly took a liking to me. But all these were below the surface and we remained normal friends and colleagues. She was quite fun to be with - and sometimes we hung out together with another lady colleague (who was also quite hot).
We kept in casual contact after I left the company, chatting online once in a while.
Many years later, work took me overseas. And while I was overseas, we started chatting online more. As the chats got more frequent, we got to know each other better. She was quite an open person, and soon, sensitive topics like personal life, feelings, relationships and even sex were broached.
As it tends to happen in online chats, you tend to get horny sometimes chatting late at night, and distance tends to make a person more brave, or reckless. One evening, I confessed to her I lusted after her. She was a bit taken aback, but wasn’t offended. Soon the conversation got dirty, and she in turn confessed to me she liked me and lusted for me as well. Sometimes conversations got really steamy, and we joked that if we were in the room, we’d definitely have fucked, but of course, we were separated by distance.
After that chat, we kinda got closer to one another and sexual topics would pop up occasionally, and we both didn’t mind it. After all, the chats were online, so it didn’t make our friendship awkward.
A few years later, I returned to Singapore, and naturally we met up in person to catch up. We both pretended that those sexual chats didn’t happen, but the fact that they did happen put sexual tension into our encounters, at least from my end. She was older (so was I, obviously) than when I first met her, but still hot. And I still like her personality. Often, I harbour thoughts about fucking her. I wondered how it would feel to see her naked, and to be inside her. These thoughts inevitably resulted in DIY sessions, all of which were quite intense. But DIY relief tend to be temporary. Lustful thoughts about Jean always come back.
The seeds had been planted.
Jean and I chatted on WhatsApp.
Soon, sexual topics returned. I was probably the one who started it, but she didn’t seem to mind the topic. Like when I was in the US chatting with her online, we shared our prior experiences and our likes in bed. Obviously, it was a turn on chatting with her about sexual topics, especially when I knew we had the hots for each other.
I wanted to do more than chat with her about sex. I wanted to do it with her. I was seeing someone, but the lust for Jean didn’t simmer.
Finally, one night, after chatting with her on WhatsApp, I plucked up the courage to ask if she wants to do it for real. Again, she was taken aback. She rejected me, citing the reason that it would not be right, since I was seeing someone. I tried to persuade her, but to no avail, although she mentioned that she’d probably gladly do it if I were not attached.
Over the next year, I propositioned her several times, each time to be rejected, but a few times coming close. On the few times she indicated the possibility of doing it, either she or I got cold feet and backed out at the last minute. Somehow, both of us felt a certain discomfort because of my status and because we were wary of how it would affect our friendship.
We did continue our chats, and we would joke about how if we were colleagues in the same company, the proximity would make it happen. I imagined her as a colleague and jerked off to that scenario countless times, and I suspect she did the same, perhaps with less frequency as me. A few times, we have sex chats where we described what we would do to each other, while masturbating to our imagination. It was hot. Very hot.
As luck would have it, one day she told me she was joining my company! One of the first thing that came to my mind was: would it finally happen now?
The day of her joining my company came quickly.
We met up, amused and somewhat excited by the fact that we became colleagues again more than a decade after knowing each other at work. We had coffee and meals a few times, and I clued her in on the workings and culture of the company.
We continued chatting on WhatsApp, and before long, I propositioned her again. She was again apprehensive. I was again persistent. After some time, on a few occasions, she agreed to do it with me during lunchtime, but these occasions never translate into real encounters: either of us would be waylaid by last-minute meetings, or either of us would have cold feet. We both wanted to do it, but yet were scared of doing it. What would we feel if we do it? How would our relationship change?
Finally, one day a couple of months after she joined the company, both of us finally plucked up the courage to meet up at a motel during lunch.
I was very nervous and excited at the same time. How would it be like? Would I be able to perform? Or would I be so nervous that I can’t get it up? Would she find me a turn on? Would either of us back out at the last minute?
We were based in difference offices, so we had to cab to the motel separately.
When I saw her at the motel lobby, my heart was pounding. I took a deep breathe, walked up to her and made a silly joke to ease the tension, then walked into the motel lobby to register a room.
It was a little surreal as we both handed our ID to the recep, then went into the tiny lift. I scanned her in the lift - she was wearing a buttoned blouse with a skirt, just as I requested. I could make out her shapely body. I felt a twitch in my crotch. We didn’t talk a lot in the lift - I guess we were both awkward inside.
We reached our floor and headed to our room. When we entered the room and closed the door behind us, we both knew there was no turning back. In maybe 15 minutes, we would be having sex. My cock would be in her pussy, as we had both imagined and talked about, as we had both wished for and at the same time apprehensive about.
I showered first. In the shower, I cleaned myself thoroughly, and gave myself a few jerks to check if I would be able to perform. I did harden. But that doesn’t guarantee performance when I see her later.
I went out in a towel, with my top naked. Although I gym infrequently now, I guess I’m still in ok shape, so I’m confident, at least in the body condition department.
Before she went into the bathroom, I asked that she come out dressed, she kinda said “orh” before closing the door behind her.
She didn’t take long, but it seemed quite long to me as I listened to her shower, and imagined her getting dry and dressed when the shower stopped.
She stepped out in her blouse and dress.
I stood up and faced her.
I guess we were both nervous and awkward inside, knowing what would happen next.
I made the first move, putting my hands on her waist, and pull her for a kiss. She did not resist and returned the kiss. It was good. She tasted good, and her tongue rolling against mine made me hard. I made the first sexual move by moving my hand onto her breasts, feeling her cup Cs over her blouse and bra. Although I could not feel much through the padded bra, it got me very hard. I was actually caressing the breasts of Jean! I unbuttoned the first few buttons of her blouse to reveal a black bra. I got braver and inserted my hand into her bra to touch her breasts. They firm and so nice to the touch - I got even harder. She let out a few soft moans as my hands explored her breasts and pinched her nipples gently.
At this point, any sense of awkwardness was lost. She reached down and pulled off my towel, revealing me in my full naked glory. Her hands closed on my already hard cock and started to stroke me. I looked down. The sight and feel of Jean stroking my cock was a tremendous turn on. I got even harder and could feel my cock pulsating in her hands.
I removed her blouse and tried to unhook her bra, but fumbled in my nervousness. She helpfully assisted me, and in no time, her bra slipped off her shoulders and I was treated to the sight of her breasts. They were very nice Cs, firm and very shapely, just the type that I love. I groped her with both hands.
Then, I reached down. pulled up her skirt and reached for her crotch. To my surprise, I touched bare skin - she wasn’t wearing panties! I found her pussy and began to massage her pussy lips and clit, which was already moist to begin with. Before long, she lost her skirt and was stark naked. I admired her body in its full glory - she wasn’t as slim as she was in her 20s, but she was shapely and very sexy. Her breasts and completely shaved pussy were very beautiful, exactly the type I like. I was extremely turned on and can’t believe what I saw.
Perhaps to break the awkwardness of me staring at her body, she bent down and took my cock in her mouth. My already hard cock stiffened further. I stood there, with soft knees, looking down at Jean sucking my cock. It was almost an unbelievable sight - Jean, a long time friend whom I’ve lusted for so long has my cock in her mouth. Her technique was soft, and very sensual, which brought me close to orgasm in a matter of minutes.
Not wanting to end it with a blowjob, I pulled out. I tore open a condom pack which I left at the side table previously and rolled it on. Jean knew what was coming and laid on her back and spread her legs. The sight was again, a massive turn on. A very sexy woman friend nude, with her legs spread for me on bed! Those sumptous breasts with erected nipples. That sweet looking and wet pussy.
I climbed on top of her and placed my cock between her legs.
“Can I?” I asked.
She nodded, with a faint smile.
I rubbed my cock head at the entrance of her pussy lips. We both moaned. It felt good. Then, I gently prod her pussy lips open and pushed in gently. I could not go in easily. Jean was wet, but her pussy was tight. Not wanting to hurt her, I pushed slowly, and asked if she was ok. Obviously she felt pain but her moans suggested the pain was mixed with pleasure, so I went even more slowly, moving my cock head in and out so she can get used to it. After a while, I started to firmly but gently push my cock in.
“OK?” I asked, concerned.
“Just push it in…” she muttered.
With that approval, I push my cock all the way in. My engorged cock head had to get over a tight segment at the entrance of Jean’s pussy. Once that was crossed, my entire cock slid into her.
It was almost unbelievable. My cock was in Jean’s pussy. I was fucking Jean. It was a decade-old fantasy come true!
She was so tight. I could feel her tightness and warmth wrapping my cock. The feeling, both physical and emotive, was heavenly. I could feel my cock pulsating in her.
I began to pump and fuck her. At first, she seem to experience a bit of discomfort. But after a few strokes, the discomfort disappeared as she got wetter, and she began to enjoy it as much as I was enjoying it. She moaned as I pushed my cock in and out of her. The look on her face was one of pure ecstasy. She had been lusting for me as long and as much as I had been lusting for her. I moaned together with her, trying very very hard to hold my orgasm as her pussy gripped my cock ever so tightly. I didn’t last very long. After five minutes, I felt a tingling in my cock and grimaced.
“Can I cum, Jean?”
She was moaning so hard she could not reply. She whimpered and nodded.
I’ve always found a woman giving permission for me to orgasm in her a big turn-on. With that, I exploded in her.
I had fucked Jean. Wow.
We chatted on WhatsApp, and found that both of us enjoyed the session. That meant that that there would be a next time. We exchanged more notes of our likes and dislikes, and of course, all those chats were a turn on for us.
A few weeks later, we were ready for a second round, and this time, I wanted to be a little more adventurous. I checked with her, and she said she likes surprises. Gradually, I began to develop a plan for the next round in my head.
Again we met in a budget hotel during lunchtime.
I showered first, and came out with a towel wrapped around myself. She went into the bathroom after me.
As I heard the shower run while she was in the bathroom, I removed the towel and sat on the bed. I could make out her silhouette on the frosted bathroom window. I remembered how her body looked like and remembered our first encounter. Blood rushed to my groin, and I was hard in no time.
I sat leaning on the pillows on the bed, opened my legs, grabbed my hard cock, and started to stroke myself. It felt very good. I pulled my foreskin all the way back to reveal my cock head. It was swollen, reddish, and throbbing. I was turned on at the sight. I continued to stroke myself, keeping myself very hard, and imagined how I’d be fucking Jean again in a while.
The shower stopped, and I knew Jean would be out soon.
I decided to continue doing what I was doing. She had told me before that she’d find it a turn on to see me jerk off. So why not let her enjoy a quick show?
Jean stepped out of the shower, clothed like the last time. She was visibly surprised to see me sitting on the bed, totally naked, stroking my hard cock.
Jean was slightly embarrassed. She looked away a little and smiled sheepishly. But clearly she didn’t mind.
I stood up and stepped towards her, backing her to a wall in the small room. She was still a little embarrassed and blushed a little. I grabbed both of hands, pinned her against the wall and kissed her. Our tongues locked, and I pressed my naked body on her fully clothed body.
Things got hot quickly. She hugged me tight, then her hands wandered over my body, caressing my chest and reached down. She grabbed my hard cock when she found it, and began to stroke me like it was the most natural thing for her to do.
I was equally aggressive. My hands were all over her breasts, and I reached into her blouse and bra, groping her and feeling her up everywhere. I reached down and grabbed her butt, then moved my hand under her dress and placed my palm on her crotch. This time she had her panties on.
I massaged her pussy lightly through her panties with one hand, and groped her breast with the other. She moaned and gasped for breath as we kissed.
I pulled her panties to the side a little and used the tip of my finger to lightly stroke her now moist pussy lips. She got wetter after a few strokes. My finger found her clit, which was wet as well, and started to massage it gently in a circular motion.
She broke off from our kiss momentarily and whimpered.
I squatted down, pulled down her white lacy panties, and beckoned her to sit on the sofa chair next to the bed.
She sat down. I hitched up her dress and spread her legs open, propping one of her legs over the arm of the sofa and her other leg on the bed.
I knelt down on both knees between her spread legs, with her wet, clean shaven and spread pussy staring me in the face.
I looked up and made eye contact with her. She was embarrassed, and closed her eyes to avoid eye contact. But she was also clearly aroused. And she showed no indication that she wanted me to stop.
I lowered my head, and planted a few soft kisses on her inner thighs, followed by kisses on her pussy lips. I heard her take a few deep breaths.
I stuck out my tongue and gave her a light lick at the bottom of her already wet pussy lips. She tasted very good - a little sweet and mostly neutral. I was eating Jean’s pussy! Just like I had longed for, and just like she had said she would like me to do.
Jean started to moan after a few soft licks. I started to lick her from bottom of her pussy lips right to the top, increasing the pressure and the tempo. Her moans grew louder, and she twitched a a few times when my tongue hit sensitive spots along her pussy lips. She was very wet now, and I couldn’t differentiate her pussy juice from my saliva. Her pussy lips and opening were just glistening wet.
I looked up, and saw that she was looking at me doe-eyed, not quite as embarrassed anymore after my tongue triggered waves of sexual pleasure on her most intimate bits.
I reached up, pulled the neckline of her dress down to her shoulders to reveal her black bra, then pulled down her bra. Her two breasts spilled out, with erect nipples.
It was a most erotic sight.
There she was, slumped in a sofa, panty-less, dress pulled up and legs spread, with her breasts hanging out of her bra. I was kneeling between her legs, with her pussy inches from my face and bare breasts within reach.
I stared at Jean for a moment, relishing the sight. She noticed, and got embarrassed again. But this time, embarrassment not the only feeling she felt. She blushed and closed her eyes halfway as she met my gaze. Her eyes and expression flashed a very sexual look. She made no attempt to close her legs or cover her breasts. Instead, she bucked her hips a little, stretched open her leg a little more, placed one of her hands on her stomach and her other hand on her inner thigh. Not only was she obviously in heat, she was feeling very sexual, sexy, lustful and wanted. Jean was enjoying the moment. Legs opened, breasts revealed, in an almost crude sexual position, with a naked man who obviously lust for her sexually, who is kneeling in front of her and pleasuring her with his tongue.
Knowing that she was enjoying it as much as I was made me crazy.
I lowered my head and continued working on her pussy with my tongue. This time, I frenched her pussy, moving my tongue all over her pussy - along her pussy lips, outside, inside. She moaned with approval. That got me to a new high - and I made a sudden grab of her left breast with my right hand, and grabbed my hard cock with my left hand. I was eating her pussy, groping her breast and stroking myself at the same time. I was hitting all her sexual spots and my own sexual spot.
I felt like I was in heaven.
I glanced up, without lifting my lips and tongue from her pussy, and saw her looking down, face tightening with ecstasy. One of her hands was caressing her other breast now, and every moan that came out of her was an expression of intense sexual pleasure.
For a moment, I imagined what things looked like and felt like from her perspective. She was staring down at her own bare breasts and open legs, with a naked man frenching her love hole like it was nectar, and seeing him overwhelmed with lust as he played with his hard cock, while kneeing between her legs.
She must have felt like a sex goddess.
Indeed Jean was my sex goddess. One whom I worship and privileged to serve. I longed to put my cock into her and fuck her, but I need to first pleasure her with my tongue, and what better position to pleasure a goddess than to kneel naked between her legs? I felt good kneeing between her legs. I felt good eating her pussy. What a privilege to serve a beautiful woman like Jean in this way. What a great feeling to witness Jean enjoy what I’m doing for her sexually. I felt so sexy and sexual eating her in this way.
My tongue zeroed on her clit, which was now swollen and red, and I swirled my tongue around her clit, sucking on it lightly occasionally.
Jean went wild and buckled uncontrollably on the sofa as my tongue circled her clit. She got very high, but for some reason, she could not reach orgasm.
It was time to try something else.
I peeled off her clothes piece by piece - her dress, blouse and bra - until she was stark naked. Then I got her to get onto the bed.
As she climbed from the sofa to the bed, I climbed up the bed behind her and hugged her from behind as she was on her knees. My right hand reached down to her crotch, and cupped her pussy. I ran my middle finger up and down her pussy lips. She moaned, and I felt her pussy getting wetter. My finger found her clit, and I began to massage her clit with my finger tip, while my left hand groped her breasts from behind and pinched her nipples gently.
I was masturbating Jean. She loved it and could not stop moaning as I played with her clit. I slowly increased the tempo, and her moans and breath got faster and faster. Playing with her pussy and breasts, and listening to her heave and moan got me extremely horny, so I pressed my hard cock against her butt and humped her.
After a few minutes, Jean let out a yelp and I felt her body shudder involuntarily. I kept moving my finger tip on her clit, and she shuddered a few more times, before collapsing onto the bed, face flushed and breathing heavily. She had came.
At that moment, I really could not take it anymore. I needed to put my cock into her pussy. I tore a condom out of a pack and rolled it on quickly.
Jean was spent, but she knew what I want and what I need. She opened her legs exposing her wet and swollen pussy lips and clit. After all I’ve done to satisfy her, I’ve earned my reward. I can now put my cock into her to fuck her.
I almost desperately shoved my cock into her. It slid in easily and we both moaned in relief as I filled her up. Her warm and wet pussy felt heavenly, exactly like the first time I entered her. I started to fuck her with long and hard strokes. I knew I would not last if I fuck her this way, but I could not help it. I was too horny and badly wanted to cum. Sure enough, after just five or six strokes, I felt a tingling and was about to burst.
Jean knew I was close and whimpered in between her moans “don’t hold, cum… just shoot in me… just fuck me and shoot in me…”
Who can hold back when you hear a beautiful woman utter such words?
With a loud grunt, I pushed my cock deep into Jean and came in her pussy.
We started messaging each other as we made our way back to office in different cabs.
It turned out we were both quite blown away by the session.
I told her I love her body, completely enjoyed the session and felt very privileged to serve her like a queen. She said she found my body and abs to be a big turn-on, and she felt very sexy and wanted when she spread herself on the sofa while I ate her pussy. She revealed that she always had difficulty coming, and very few men can make her come. Most of the time, she had to DIY after sex for full satisfaction. She was thrilled and very satisfied that I brought her to the big O by masturbating her. I think she felt closer to me because I was a rare one who could make her cum. We both got horny messaging each other and I was sure we could do Round 2 immediately if she was with me. But work beckoned.
I found it hard to concentrate on work that afternoon as my mind kept wondering back to the session we had. Finally I had take matters with my own hand with a trip to the gents. After I was done, I messaged her and told her I had to DIY and thought of her the whole time. She sounded pleased that she had such a lasting effect on me, but chided me for making her horny again. I responded by asking her to go to the ladies to take care of things.
Unfortunately, work was busy for both of us in the next few weeks and we had no chance to meet up.
One day, she had to come to my office for a morning meeting, but she had to rush back to her office right after lunch time. We could meet, but we had only an hour or so, and that wasn’t enough for a tryst at a motel.
I had a lot of pent up lust for her. So I suggested a quickie in a toilet. She was reluctant, considering the discomfort and the risks. Plus we were not exactly teenagers or youngsters in our 20s anymore. Which early 40s couple have quickies in public toilets?
But we did not have options, so I tried to talk her into it. After some persuation, she agreed.
We decided to try an adjacent office building which gives public access to its lift lobbies and toilets on every floor. Acting as nonchalent as possible, we randomly picked a floor. The first choice was no good, as there was a lot of foot traffic. The second choice was no-go as well, the disabled tolet was occupied. The third choice looked promising - the disabled toilet was unoccupied, and traffic was minimal.
We loitered at the lift lobby, which was near the disabled toilet for a while, making sure the coast was clear. Then I gave her a signal and we both hurriedly walked into the disabled toilet, closed the door, seconds before a bunch of men who were headed for lunch walked past the toilet. Our hearts were pounding. No one had seen us, but it was quite risky. But it was quite exciting as well.
Quote:
Originally Posted by
xrage
another super steamy update! I like your fast pace. Descriptive and lots of action. and regular updates. Thanks TS!
Jean is one hot lady. She must be in her late 30’s in this story? or real encounter?
That would put her as a steamy hot MILF!
We are both early 40s. She is single so technically not a MILF. 100% real encounter.