Hi all,
I would like to share my experience with an ex-classmate from Primary school. It happened to me recently and ever since our first encounter. It has become more like a weekly affair.
Esther (not her real name) was an ex Primary school classmate of mine. During our time, she was like the school belle of our cohort. However, being in primary school, most of us never knew what was like to go after girls. The boys were more into playing marbles and soccer. She was in the Chinese dance club and every time we had a school function, she will be the lead dancer for the performance.
Of coz, after our PSLE, we all parted ways but recently I finally met her again after more than 20 years! Our kids were studying in the same enrichment class and that fateful day we were both waiting outside for the kids to finish class. At first, I was wondering why this lady kept looking at me in a knowingly manner. I couldn’t remember her at all. I was just playing it cool and not looking directly at her but then it struck me! I calmly went up to her n smiled and asked:
Me: hi, r u Esther from **PS?
Esther: yes, *my name*, I tot u looked familiar but I didn’t dare to ask u. U didn’t change much over the years! Still got the boy boy look.
We both laughed. Esther looked like great, long hair, nice skin, slim with nice looking B cups (which I don’t remember her having, she was more like an A cup back in primary school). We quickly exchanged numbers coz the kids were coming out from the classes already.
After we exchanged numbers that day, I didn’t think too much about it. But later that week I received a whatsapp from Esther. It was casual talk, mostly asking about whether my kid is enjoying the enrichment class n what plans do I have for primary school, am I gonna enrol in our alma mater.
After that the questions got to asking about our families and our partners, how long have I been married, where do I stay n how many children etc…pretty harmless. N I didn’t thought too much about it. Neither did an affair with Esther cross my mind. So after some chit chat, I casually said we could have coffee while we wait for our children. N she agreed.
So the following week, while our kids r at class, we had coffee together. I think she dressed up purposely that day coz last week when I saw her, she had no make up on n she was like in berms n an oversized t-shirt. Today, she put on make up n was wearing a dress n that’s when I noticed her cleavage and how hot she still looks. We had a good time talking n laughing n reminiscing about our primary school days.
When we parted ways, she said we will have coffee again next week.
N I said I can’t wait n will be counting down the days.
So thru out the week we started messaging each other frequently. N there were always hints of flirting like “I can’t wait to see u again”…“if only I had the balls to date u when we were in primary school”, we would go on about how it might turn out, how our kids might look like etc…still, I never had any intention of an affair. It was purely for fun n I tot she was just being playful.
I found out that she stays the block behind the school n that she’s been a stay home mum since the birth of her 2nd child. During the time of her first child in enrichment class, her husband is driving their 2nd child to music class n he will be waiting there for 2hrs. I also found out that they don’t really go out much as a family nor does she n her husband goes for dates n they’ve never been on a family tour coz they’ve been saving to buy a condo.
So came the next time we met n we were chatty and flirty n I jokingly asked if her hands would’ve felt the same as in primary school (we held hands before in lower primary n walked to recess as a class). N I reached out to touch her hands. She pulled away laughing that it’s now rough with all the housework n I said I need to feel it longer to know. She was shy n said people might see. So i didn’t pursue.
I had to fly out for work for the next weekend and my wife went to pick our kid up instead. When I was overseas I received a text from Esther saying that she saw my wife picking up my kid and she thinks my wife is pretty. I said my wife always use SKII n Esther said maybe she should use it too. I laughingly said she had more natural beauty than my wife. She ended by saying she misses me and hope to see me next week. I said I miss her too n gave her a kiss emoticon.
Anyways, I only came back two weekends later and we were constantly messaging each other when I was overseas. We talked about everything n anything. I was really counting down the days to coming back n seeing Esther. I finally touched down in the early morning n I volunteered bringing our kid for class even though I was extremely jet lagged.
Esther’s face lit up when she saw me walking my kid to class. I could guess she wasn’t expecting me as she was dressed in frumpy home clothes. After our kids were in class, I asked her to walk with me to the MSCP as I have something to give her.
She was asking me all sorts of questions about my trip as we were walking to the car. I could see she was mighty impressed with my Porshce Cayenne. I took out a Coach shopping bag and a SKII shopping bag n gave them to her. I bought her the whole range of Coach bags, from the coin pouch, to the passport holder, to the wallet, wristlet, handbag and tote bag. All were matching and from the same range which I got at the Outlet. I also gave her some SKII products which I got from the duty free. She was speechless.
She pushed the shopping bags to me and said she couldn’t accept the gifts. I insisted and said that it’s no problem at all. After a while she relented. She said she needs to bring them home immediately to hide from her husband n she asked me to walk her back.
As we crossed the road to her house, I put my hand at her lower back gently to rush her as there were cars approaching. I volunteered to wait downstairs while she goes up to hide the bags. After she’s done that, we walked back to have coffee while waiting for our kids.
Over the rest of the week, she kept thanking me for the gifts n we eventually agreed she will buy me a meal to thank me. So we decided that we will have dinner together after our kids lesson.
The weekend came and after we dropped our kids home after the lesson, I went to pick her up. She was really dressed up in a nice top which revealed her ample cleavage n a nice skirt n heels. She also wore a cardigan over her top. Her hair was untied and she had some light make up on. N when she entered the car, she smelled heavenly from her perfume.
We had dinner in a nice restaurant in Sentosa and after we opened the 2nd bottle of red wine, she took off her cardigan as she was feeling warm. Her face n skin was flushed rosy red from the alcohol n she was chatty n laughing. After dinner we went for a walk along the beach n she tripped once on the uneven pavement n I quickly reached out to hold her steady. Subsequently I was holding her waist n she was leaning on me as we walk. She took off her heels n walked on the sand.
After a while, we sat down on the sand facing the lagoon. She was leaning on my shoulder n she commented I had a comfortable shoulder to lean on. I leaned towards her face n breathed in the alcohol on her breath. I saw her eyes were closed n her lips parted slightly so I took a leap of faith n kissed her gently on her lips…
That was when the floodgates opened…
We started frenching passionately n Esther was letting out soft moans. I kissed her cheeks n down the side of her neck n her ear lobes n I tongue her ears gently. I could feel her goosebumps on her arms n she was hugging me tightly.
She broke free from our kiss n stared at me. I felt a pang of guilt n kept quiet. We got up n started walking again along the beach in silence. I realised that we were getting further from the carpark n we were in a quite secluded part of the beach. Esther realised that too but she continued walking n I saw a toilet ahead, so I figured she was heading for the toilet.
When we reached the toilet, she went in without a word while I stayed outside for a smoke. I finished 2 sticks n realised she’s not out yet. Since there was no one around, I went into the female toilet to look for her. She was standing over the basin n she looked like she had been crying.
Esther looked at me in surprise but I moved forward n she stepped forward n hugged me. We started frenching passionately again n my hands were roaming up n down her back and her butt. Her butt was soft to touch and it felt so good to be grabbing them firmly.
Somehow as we were kissing, we were twirling round n we ended up in the last cubicle. We locked ourselves in the cubicle and I sat on the toilet bowl while Esther straddles over me. She lifted up her top n I unbuckle her bra n her exposed breasts faced me. They were bigger than I thought! Slightly saggy with dark nipples. There were some creases and stretch marks on her stomach n she saw me looking at her stomach n she used her hands to cover her stomach. I pulled her hands away n gave her light pecks over her stomach to assure her it’s fine. She arched her back n I grabbed both her breasts and started sucking on her nipples hungrily. I was alternating between each nipple and I was kissing n licking the sides and under her breasts n she was moaning lightly to my kisses n touches.
Please bear with me as I’m still under moderation, hence the rest of the story is still stuck…the juicy bits are ready to be served!!!
As I was enjoying her breasts, Esther has been grinding me hard n I was getting uncomfortable as my dick was gonna explode under my pants! Esther was clearly enjoying herself as I can see her eyes were half closed n she was biting her lower lip n as she grind herself harder against my dick, she was grabbing her own breasts and pinching her nipples. It was seriously an arousing sight!
Suddenly Esther was grinding harder and faster against me and she suddenly hugged me hard and her body was convulsing in spasms n she was moaning softly into my ears and once in a while she will lick my ear lobes n kiss my neck. As she reached her orgasm, Esther was frenching me hard while my hands were grabbing her butt cheeks from under her skirt.
When she finally got off me, there was quite a big stain on my khaki coloured pants! She was clearly embarrassed as she covered her mouth in surprise. She helped unbuckle my belt and with one smooth action, pulled down my pants and boxers n my dick sprung up full mast in front of her face. She was pleasantly surprised to see my entire dick area was cleanly shaven and smooth. She was examining it, turning my dick to the left n round and checking out my smoothly shaven balls, and giving small pecks around the dick area. She was stroking my dick gently n she was using her tongue to twirl around my dick head. She licked the entire shaft of my dick n sucked gently on my balls before licking back up the shaft and twirling around my dick head. She then engulfed my entire dick into her mouth and started sucking me off. She will alternate between sucking my dick n licking my dick head n stroking me. It felt really really good….
As she was kneeling down sucking me off, I would lean forward n grab her breasts n sometimes I’ll hold her head down to deep throat me. She gagged a few times n she slapped my thighs Everytime I make her choke. Soon I could feel the eruption coming n I whispered to her that I’m coming and I wanna come in her mouth. She just nodded her head and continue to suck me off. As I was going to I leaned back n Esther took that as a signal and started jerking me off and sucking me hard and fast…that feeling….oh damn….and I just released all my soldiers into her mouth. Probably due to that long foreplay and her grinding, there was a huge build up of sexual tension that when I ejaculated, it was wave after wave of sperm and until a certain point she couldn’t take it no more and pulled my dick out and continue to jerk me off and my sperm was flying all over the place! Some landed on her cheek n some in her hair and more on the floor. She gave me that look of bewilderment…it was priceless.
Esther spat out my sperm from her mouth into the toilet bowl and flushed it away. I was helping to wipe the sperm off her cheeks and those in the hair was a bit challenging. She also helped wipe me clean. After we dressed ourselves up, we walked out of the cubicle, drank some water from the water cooler outside and started walking back to the car. We held hands but we were silent throughout the journey back. N even when we got into the car, the entire drive was in silence….
Upon reaching her place, she quietly got down the car n left. Not a word was said, neither did she look at me…even during the drive home, she was staring out of the window.
At that moment, I was feeling extremely guilty and I didn’t dare to text her when I got home. The week passed and when I sent my kid for class, Esther’s husband was sending their child instead of her.
Another week passed n she finally texted me. She said she was confused that night, her husband was her 2nd bf and he was the one who took her virginity. She has never had a CIM before, even though her husband always requested for it. She n her husband hardly have sex after the birth of their 2nd child. She’s always tired as she’s a stay home mum n she suspects her husband don’t find her attractive anymore. She said I always make her laugh n feel special whenever we have our coffee while waiting for our kids. She said the attention I spent on her breasts was longer than an entire session with her husband. She also said that she has never had an orgasm before n that night she wasn’t sure if that was an orgasm.
Esther went on to say that nothing will ever come out of our relationship. Coz she can see that I’m successful n have a great family n I probably have had more similar encounters with other women (she’s not wrong on that). She asked for my forgiveness for keeping quiet after that night as she was so confused and guilty that she didn’t know what to say. She hopes that we will still be friends and I will forget we ever had that encounter.
I really didn’t know what to say to all that she said. In the first place, I’ve never had the intention to have an affair with her. I was ok with it being a one off encounter but somehow there’s this nagging feeling in me that there is more to Esther that I can bring out in bed. I gotta play it cool and not scare her off anymore. So I said I was happy that we could still be friends n I look forward to our coffee sessions over the weekend.