(Part 2) I was a toyboy for an older woman, and then her friend [MFF]

I posted a few weeks ago about an experience I had being a toyboy for an older woman. I had a great response as well as some kind and fun DMs. A few people asked specifically about the evenings spent with Lucy’s friend, Caroline. I have a free afternoon so thought I’d post a follow up.

[Original post.](https://www.reddit.com/r/gonewildstories/comments/narqwx/i_was_a_toyboy_for_an_older_woman_and_then_her/)

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I arrived at Lucy’s expecting a normal evening – usually these were some combination of sex, cuddling and chatting, takeaways and maybe a film. However when I arrived Lucy greeted me in a tight short black dress and heels. It wasn’t unusual but we’d normally chat and decide how the evening would progress. She immediately told me that she had a surprise for me, but that I had to follow her instructions and stay quiet. I agreed and she kissed me, telling me we’d both enjoy the evening. She led me upstairs and into the second bedroom, where she asked me to strip naked and placed a collar around my neck. She then attached a lead and put a blindfold on, but kept it above my eyes. She started caressing my already erect cock and told me she was so excited for the surprise, and asked if I was ready. I told her I was and after a few more passionate kisses she lowered the blindfold and whispered that she’d lead the way. We entered her bedroom and she stopped me at the side of her bed, as I was familiar now with the layout of her house and room. Lucy stood beside me and started caressing my cock again with one hand, and said “you can open your eyes now Caroline” and I instantly could guess where the evening was headed. I’d never met Caroline before and so was excited by what would be to follow, and I heard her say “wow, you’ve told me so much about him” – as mentioned previously Caroline and Lucy were very close and Caroline had known for a while in quite some detail about Lucy and I’s relationship. I heard Caroline get up, and could feel the change in tension on the lead as Lucy handed it to her saying “he’ll do whatever you ask, he’s yours for the night. I’ll enjoy the show until you’d like to invite me in”.

I heard Lucy sit down and felt Caroline’s hand brushing against my cheek, down my neck and chest and around my back, and could sense she was standing to one side of me. Lucy then said “Caroline, I know it’s been a while but he’s a good guy. Take your time and enjoy the evening.” Again as mentioned I’d heard that Caroline had been through a divorce and it had been a while for her, she again returned to exploring my chest and arms with her hand and I could feel her breath on me. Caroline then told me to kneel down, and stepped in closer to me. I could sense her thighs in front of me so started gently kissing and licking them, slowly over a few minutes working my way up closer to the hem of her skirt. As I could sense the warmth from her pussy she slowly turned around, gently leading me with the lead as she sat on the bed before pulling on the lead to bring me in closer until my mouth greeted some lace underwear. I got to work with my tongue and mouth and could hear Caroline beginning to moan and getting wetter beneath the lingerie. I love giving oral, especially with that added element of being “forced” to, although I’d have jumped to do so willingly, and so I lost track of time trying to please her and not become a panting mess.

By this point Caroline’s underwear was absolutely soaking, the moans were getting far louder and I heard Lucy say “I told you he wasn’t bad at this.” Whereas before Caroline had sounded like she was very well spoken, she then said quickly and between moans “I want you on the bed” and dragged on the collar to pull me up. Lucy must’ve placed the bed-ties we’d used on the bed pre-emptively as Caroline quickly spread my arms and had them cuffed before climbing onto my chest. I felt her above me and her soaking panties again pressed onto my mouth. After a few minutes she climbed off and quickly spun 180 degrees, and when her pussy was pressed back down onto my mouth the lingerie had been slid to the side. Her pussy tasted so great and was dripping wet. I felt her start to caress my cock, still rockhard from earlier before she took it in her mouth. Considering she’d not had sex for a while she was great at giving oral, especially as I continued to bury my tongue in her pussy!

Again I lost track of time but I quickly felt like I was close to cumming in Caroline’s mouth, and I think she sensed it too as she stopped giving me oral and was quickly unwrapping a condom (Lucy had clearly prepared well) and putting it on me, before climbing off my soaking face and quickly sliding my cock inside her. At this point there wasn’t any stopping her, she was moaning loudly and doing most of the work. I can happily say that she fucked me in this instance, and after what felt like only a few minutes she was having a very loud orgasm with my quickly following. She continued to slowly ride me before laying down on top of me breathing heavily. I heard Lucy from across the room say “I think you needed that Caroline” to which Caroline laughed between pants. After a few moments she began kissing me passionately, before saying “I already want to fuck you again, poolboy” to which we all laughed – I was still somewhat erect and inside of her, and wouldn’t have put up any protest had she started again.

A few more kisses and then Caroline removed my blindfold, so I could finally see her. Although I’d seen pictures so was still far better looking in the flesh. Red-faced from the previous few minutes and what I’d say is a typical mum’s body, a few sizes larger than pre-kids but still a lot of nice curves, and a tight red dress and red lingerie to boot. She said to both Lucy and I, “I know the night isn’t done, but thank you both” and kissed me again. I could see Lucy sat in a chair, legs spread with a vibrator on the table next to her – she’d been enjoying the show a lot!

Caroline climbed off, and at the side of the bed removed the dress to reveal a matching red lacy bra, which was also removed. Finally she removed the panties, and with a grin said that Lucy had told her I loved being gagged with expensive lingerie and she placed them in my mouth, climbed back onto the bed and said to Lucy “I best clean him up”, as she took the condom off and started giving me oral again. Shortly after I came in her mouth. Lucy went to get us drinks and Caroline undid the cuffs. On Lucy’s return she sat on the bed, Caroline cuddled up to me and I asked her if she’d had any of what had just gone down planned. Caroline replied that she’d had a lot of time on her own, that her toys got had had a lot of use during the divorce and she’d watched a lot of porn. She mentioned that everything previously had been quite vanilla and she wanted to try some new things, and that Lucy had also made some suggestions. I’d been quite surprised, pleasantly so that we’d not just gone straight to missionary too!

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I’ll leave it there for now but please let me know if you’d like to hear more, either in the comments or DMs!

Source: reddit.com/r/gonewildstories/comments/nwly4m/part_2_i_was_a_toyboy_for_an_older_woman_and_then