Trying bi for the first time
Hot Hook Up - A Fantasy - 11 Aug 2026
Anna was the sales manager for a large company in Perth, she had 20 staff working under her. She was dynamic 5ft7in tall light brown hair green eyes d size firm breasts in very good shape , she did aerobics and went to the gym regularly, you could not tell she was 60. Her assistant Wendy had just been promoted and was moving to Sydney so Anna was on the hunt for a new assistant. There was the annual team building weekend coming up this particular weekend so Anna decided to go. Her husband Craig worked away in the mines so her weekend was free.
Friday came and all the sales staff were at work bags packed ready for a weekend away, most just went to get away from husbands and kids not for the team building, but Anna remembered what her first team building weekends were like lots of laughs and a bit of drinking. They all filed onto the bus took their seats and were on their way. Anna sat next to the weekend organiser and told her to just treat her like all the rest not as the boss, she told Anna that was her intention.
They arrived at the resort had everything they would need 5star accommodation large pool a spa large spacious rooms. They filed inside and the organiser Rachael called them together gave them a brief outline of the weekend then organised them into pairs as they would be sharing rooms. Anna was paired with Jess a short blonde athletic looking girl mid 20s she was bubbly and enthusiastic, Anna had seen her around the office she was dynamic always on the go. They went to their rooms to unpack jess was just non stop talking telling Anna how excited she was to be on this trip and how great the company was to work for, she just never stopped talking.
They all met back downstairs and started their team building, nothing to strenuous just a few talks and a couple of games. They finished mid afternoon and some of the women went to the bar, a few went for a walk Anna decided to go for a swim, she went and got changed into her bathers a modest 1piece and went to the pool. She was relaxing in the pool when jess turned up "I forgot my bathers" she sadly told Anna. "There are no guys here so just wear your bra and knickers" Anna told her." I don't wear a bra" Jess replied "so go topless" Anna replied. With that jess pulled her shorts off showing a red G-string then her t shirt Anna couldn't help looking at her small firm tits b-size at a push and bright pink nipples she felt a strange feeling in her pussy as Jess jumped in the water. They stayed in the pool for a while Anna finding out more about jess she lived in the city in a small flat with her cat , she had no boyfriend was more interested in her career than boys. They decided to get out and as jess was climbing out Anna noticed just how small and tight jess, s arse was and again she got that tingle in her pussy. They went back to their room to shower and change for dinner, Anna hopped in the shower lathering up her breasts and pussy it was slightly puffy for some reason, then she glanced up to see jess standing there watching her, slightly embarrassed she said " be done in a sec" " no rush " replied jess. Anna finished and hopped out of the shower as jess hopped in lightly brushing past Anna's naked body. There it was again that tingle, Anna glanced at jess, s pussy totally bald but she could make out a very large clit, she quickly looked away and went to get dressed. Anna's mind was racing why was she getting that tingle in her pussy? She dressed and went down to dinner, jess came down a bit later wearing a short pair of denim shorts which showed her firm arse cheeks and a tight black crop top no bra , hot Anna thought.
Dinner was a success lots of chatter and laughs and a few drinks, Anna decided to go back to her room so went back upstairs and got changed into a black silk negligee, she was sat on the balcony watching the sunset when jess came back. She came out to the balcony and sat opposite Anna. , " you look nice" jess said " thanks " Anna replied, kinda embarrassed. Jess was looking intently at Anna's breasts and she felt the tingling again then her gaze went to Anna's pussy and she licked her lips. Jess then stood up walked over to Anna and kissed her full on the mouth, Anna responded by grabbing jess, s head pulling her closer as there mouths and tongues entwined, she felt jess feeling her large breast gently playing with her huge nipple as they continued their passionate embrace. Jess squeezed Anna's nipple harder and Anna felt the first wave of an orgasm rush over her she moaned into jess, s mouth as she came. Jess then started kissing Anna's neck pulling her negligee up over her head exposing her breasts and pussy to jess. She trailed her tongue across her breasts first one then the other before taking a nipple into her mouth. Sucking gently at first, Anna moaned again. Then jess started to bite her nipple gently as her hand found Anna's pussy rubbing her now wet pussy. Jess found Anna's clit and started rubbing it well Anna just started cumming hard as jess was now biting her other nipple a bit harder now but Anna was loving the slightly painful experience. Jess slipped a finger into Anna's pussy working it deep inside her rubbing her clit with her thumb. She then moved from her nipple trailing her tongue down Anna's stomach to her pussy she spread Anna's legs and started to tongue her sopping wet pussy. Anna just lost it and squirted all over jess, s face, jess lapped at Anna's pussy forcing her tongue deeper into her as she then sucked on her clit and puffy pussy lips. Anna put her legs over jess, s shoulders and pulled her head tighter into her pussy this was absolutely the best tonguing of her life and didn't want it to end. And jess seemed to want to eat Anna's pussy forever. She reached a hand under Anna and slowly slid a finger into Anna's arse. Anna had never tried anal but this was a new sensation and she was enjoying the feeling of having jess finger her arse. Her orgasms intensified with the new sensation. Finally jess got up from between Anna's legs and said wiping Anna's juices from her mouth " I think we should go to bed now don't you" Anna just nodded she was exhausted but keen to taste her new assistants pussy. Because she had decided between orgasms jess would be her new assistant. They could learn from each other.
Friday came and all the sales staff were at work bags packed ready for a weekend away, most just went to get away from husbands and kids not for the team building, but Anna remembered what her first team building weekends were like lots of laughs and a bit of drinking. They all filed onto the bus took their seats and were on their way. Anna sat next to the weekend organiser and told her to just treat her like all the rest not as the boss, she told Anna that was her intention.
They arrived at the resort had everything they would need 5star accommodation large pool a spa large spacious rooms. They filed inside and the organiser Rachael called them together gave them a brief outline of the weekend then organised them into pairs as they would be sharing rooms. Anna was paired with Jess a short blonde athletic looking girl mid 20s she was bubbly and enthusiastic, Anna had seen her around the office she was dynamic always on the go. They went to their rooms to unpack jess was just non stop talking telling Anna how excited she was to be on this trip and how great the company was to work for, she just never stopped talking.
They all met back downstairs and started their team building, nothing to strenuous just a few talks and a couple of games. They finished mid afternoon and some of the women went to the bar, a few went for a walk Anna decided to go for a swim, she went and got changed into her bathers a modest 1piece and went to the pool. She was relaxing in the pool when jess turned up "I forgot my bathers" she sadly told Anna. "There are no guys here so just wear your bra and knickers" Anna told her." I don't wear a bra" Jess replied "so go topless" Anna replied. With that jess pulled her shorts off showing a red G-string then her t shirt Anna couldn't help looking at her small firm tits b-size at a push and bright pink nipples she felt a strange feeling in her pussy as Jess jumped in the water. They stayed in the pool for a while Anna finding out more about jess she lived in the city in a small flat with her cat , she had no boyfriend was more interested in her career than boys. They decided to get out and as jess was climbing out Anna noticed just how small and tight jess, s arse was and again she got that tingle in her pussy. They went back to their room to shower and change for dinner, Anna hopped in the shower lathering up her breasts and pussy it was slightly puffy for some reason, then she glanced up to see jess standing there watching her, slightly embarrassed she said " be done in a sec" " no rush " replied jess. Anna finished and hopped out of the shower as jess hopped in lightly brushing past Anna's naked body. There it was again that tingle, Anna glanced at jess, s pussy totally bald but she could make out a very large clit, she quickly looked away and went to get dressed. Anna's mind was racing why was she getting that tingle in her pussy? She dressed and went down to dinner, jess came down a bit later wearing a short pair of denim shorts which showed her firm arse cheeks and a tight black crop top no bra , hot Anna thought.
Dinner was a success lots of chatter and laughs and a few drinks, Anna decided to go back to her room so went back upstairs and got changed into a black silk negligee, she was sat on the balcony watching the sunset when jess came back. She came out to the balcony and sat opposite Anna. , " you look nice" jess said " thanks " Anna replied, kinda embarrassed. Jess was looking intently at Anna's breasts and she felt the tingling again then her gaze went to Anna's pussy and she licked her lips. Jess then stood up walked over to Anna and kissed her full on the mouth, Anna responded by grabbing jess, s head pulling her closer as there mouths and tongues entwined, she felt jess feeling her large breast gently playing with her huge nipple as they continued their passionate embrace. Jess squeezed Anna's nipple harder and Anna felt the first wave of an orgasm rush over her she moaned into jess, s mouth as she came. Jess then started kissing Anna's neck pulling her negligee up over her head exposing her breasts and pussy to jess. She trailed her tongue across her breasts first one then the other before taking a nipple into her mouth. Sucking gently at first, Anna moaned again. Then jess started to bite her nipple gently as her hand found Anna's pussy rubbing her now wet pussy. Jess found Anna's clit and started rubbing it well Anna just started cumming hard as jess was now biting her other nipple a bit harder now but Anna was loving the slightly painful experience. Jess slipped a finger into Anna's pussy working it deep inside her rubbing her clit with her thumb. She then moved from her nipple trailing her tongue down Anna's stomach to her pussy she spread Anna's legs and started to tongue her sopping wet pussy. Anna just lost it and squirted all over jess, s face, jess lapped at Anna's pussy forcing her tongue deeper into her as she then sucked on her clit and puffy pussy lips. Anna put her legs over jess, s shoulders and pulled her head tighter into her pussy this was absolutely the best tonguing of her life and didn't want it to end. And jess seemed to want to eat Anna's pussy forever. She reached a hand under Anna and slowly slid a finger into Anna's arse. Anna had never tried anal but this was a new sensation and she was enjoying the feeling of having jess finger her arse. Her orgasms intensified with the new sensation. Finally jess got up from between Anna's legs and said wiping Anna's juices from her mouth " I think we should go to bed now don't you" Anna just nodded she was exhausted but keen to taste her new assistants pussy. Because she had decided between orgasms jess would be her new assistant. They could learn from each other.
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