This is a continuation of my true story of my ex girlfriends daughter as my sugar baby.
It had been a year since I started fucking my ex girlfriends 13 year old daughter Destiny, she was now 14, her breasts had grown into these beautiful perky C-cups that had zero sag, she was perfect! After a long fucking session we were cuddling and she asked if I would be interested in one of her friends, I was surprised that she would bring this up and immediately imagined her friend Cassie who was absolutely stunning! Of course I would be interested – however was still very cautious. The thing about providing large sums of money is the risk of them spending it and having there parents ask questions all of a sudden – can’t have them coming clean on how they earned the money! I asked her who and why they might be interested in a sugar daddy….I waited with baited breath praying it was Cassie – but she said Erin. Erin was 14 years old, blond hair, blue eyes, but a bit on the heavier side. When I questioned her about why she would want to do this Destiny replied “she’s in a rough place at the moment with her parents getting divorced and could really use the money to help with basic needs such as clothes and stuff” . I asked if she was working at all or just in school, fortunately she had just started working a job at the local grocery store – so it wouldn’t be odd for her to have some of her own cash. I thought about it for a few minutes and agreed to have a chat with her to ensure she was actually comfortable with this. Destiny and I met up with Erin the next day to discuss details – Erin seemed excited about the idea, but a bit nervous at the same time. I suggested a threesome with both of them for a premium price, they both liked the idea but were a bit apprehensive as neither one of them had been with another girl and they were best friends. They agreed and we picked the date for my next trip the following month.
The month seemed to take forever, but the day eventually came – I had booked a nice Airbnb and they had checked into it. When I arrived they greeted me at the front door – Erin seemed really nervous. I took Destiny over to the kitchen get a feel for how Erin was doing. She informed me that they were both super uncomfortable having a threesome, but were still good to go if I wanted to have them one at a time – I wasn’t thrilled at the last minute change, but can appreciate it regardless. There was something else I also wanted so I suggested an alternative, if Destiny was willing to give me her anal virginity they could still earn the premium. Destiny agreed and wanted to go first, but I asked if they would first be comfortable showing off some of the lingerie I had brought for them. They agreed to this so I poured myself a glass of wine while they got changed. Destiny came out first, I had picked out a tight green onsie that was transparent and rode up her perfect little ass. She knew what I liked so came over and gave me a little lap dance while I sipped on my wine. While she was teasing me Erin came out in a sheer blue teddy I had got for her, it was a bit more loose fitting as she was heavier – but man did she have perfect tits! Erin sort of twirled around in an ackward was and was somewhat unsure what to do – I knew she needed some encouragement so told her she looked absolutely stunning and was dancing amazingly – this seemed to calm her nerves a bit and she eased up and had a more natural flow.
Destiny and I went to the bedroom, layed her down on the bed, mounting her and sensually made out for a while. I stood up, held her hand and had her bend over the bed, I pulled her onsie aside and looked at her tight little ass that I was bout to take for the first time. Starting from her pussy I licked upwards gently running my tongue over her anus, she flinched a bit the first few times but started pushing back onto my face by the third or fourth. I didn’t want to jump straight to her ass so took my time caressing the rest of her body. I had her bend back over the bed and lined up my cock with her tight little pussy – sliding in still makes my body quiver as she’s so tiny and tight! This time though I put some spit on my right thumb and slowly start massaging her tight little anus while gliding in and out of her, there is absolutely no question she was enjoying this as I felt her cum within a few minuts of doing this – looking down at her cum on my cock almost put me over the edge, but I had to have her ass (and I also had Erin to fuck next). I asked her if she was ready to to try anal…..she replied “I’m scared it’s going to hurt”….I told her that I had lube with me and she would be in control. I grabbed the lube, using my pinky finger to slide into her virgin ass and lube it up a bit. I took a large glob and applied all over my cock. She bent over the bed and I lined up the tip of my cock, her anus looked so tiny and tight I wasn’t sure this was going to work either. I let her know that the pace was 100% up to her and to just push back whenever she was ready. She took a minute to work up the courage and started pushing back, after a few failed attempts and reminders that she needs to relax her sphincter, my tip disappeared…it was so fucking tight and she was gripping the bed sheets as if it was a death grip, she was breathing heavy so I told her she’s doing absolutely great and to hold still while I applied some more lube – I added a bit more and told her to push back a bit further – she managed to get half of my 7” in her but I didn’t think she could take more. I told her to not try to go any further but to just go back and forth at this depth – she started slowly and eventually picked up the pace – there was a bit of blood from the tearing, but that actually turned me on a bit and she was doing great with it – at one point she managed to take ¾ of it by pushing back harder – it was at that point I couldn’t contain myself any more and erupted in her ass, I would almost feel the cum pushing back into me. As I slowly pulled out a mix of blood and cum dripped form her ass, it was a beautiful sight to see and I felt honored to have been given the pleasure. I rolled her over and cuddled her in, I asked how she was doing. She said it hurt at first, but started to feel better near the end. I asked if it was something she would like to try again and to my surprise she said yes! We cuddled for a while and chatted, I was starting to get tired, but also knew I had to fuck Erin next. I told Destiny to go see if Erin was ready.
Erin came in and I could tell that she was super nervous! I told her to just come sit on the bed for a while and we could chat. Her hands were trembling she was so nervous. I took her hand and let her know that this would all go at her pace – if at any point she wanted me to stop I would oblige, and guaranteed her she would be perfectly safe. This seemed to calm her nerves, so we stood up and I kissed her for the first time – her lips trembled and body shook as I started exploring her body with my hande…..stay tuned for part three 😊
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