“Jack was my first proper boyfriend. We’d been together a few months having met on holiday and didn’t live very far away so tried to meet up every weekend. He was two years older than me and incredibly handsome…
Piercing blue eyes, cropped dark hair, strong athletic frame and six foot two when he leaned down to kiss me. He had tattoos over his arms and shoulders which I found incredibly attractive. He was more experienced than me and with his birthday coming up I wanted to give him something special. The problem we had, and I’m guessing that most people would love having this problem, is that he was really big in the downstairs department.
I’d had flings and Grindr meets before and generally I’d been fine, but I’d dreaded Jack staying over as there was no way I could fit him in. We’d tried but it’d been too painful, and I’d been so apprehensive that I always ruined the moment. It was getting to be an issue. He was very patient, but I knew both of us were frustrated.
For his birthday I decided to really show him my commitment and so bought him a set of anal stretching toys for beginners, to use with me. He had suggested it in passing previously but I’d dismissed it as not for me. I guess I was a bit of a prude with some things, which needed to change. www.esmale.com sold a set of three stretching plugs that go from small, through medium to something that resembles Jack in size so I’d thought this was a good starting point.
To go with it I’d also bought a large bottle of lube, some Gold Max Blue pills to keep us both horny while we tried, along with some poppers. I don’t live near any sex shops so after a quick web search found www.poppersupershop.com which had a wide selection which were decently priced. I went for a multipack set with a few varieties in. Having never tried poppers I thought it prudent to get a selection.
The big day came and Jack had driven to mine. My housemates were out so I’d cooked a romantic meal and we had wine. I nervously had a little more than usual but that was probably for the best. He opened his presents, which I’d wrapped together in a fancy box, along with some horny underwear.
With every piece he took out his eyes lit up and you could tell he was getting excited. He held my hand across the table and looked into my eyes asking if I was sure I wanted to do this and whether I was ready. I said that there was nothing I wanted more than to make him happy and I wanted to bring us closer together. I really wanted it to work with Jack.
Heading up to the bedroom we passionately kissed, unable to keep our hands off each other, frantically ripping off each other’s shirts and jeans and throwing them to the floor. He picked me up and threw me onto the bed, landing on top of me and we kissed more. I reached down and felt him, huge and hard in his pants. He asked again if I was ready to which I nodded, and we each had one of the pills. It would be a long night.
With the lube and poppers we tried the smallest plug. It was pretty easy so we quickly went on to the medium, but I was glad I found out where to buy poppers. This took time and I could see the look of excitement in Jack’s eyes as he slowly teased it into me in circular motions, eager for what would come later. He took his time and was incredibly loving, kissing me and slowing down at any sign of discomfort. When it was in he played with it some more until it became comfortable, offering me poppers before each movement wider.
As I relaxed it became easier and my feelings went from apprehension to pure pleasure. Jack loved where he was able to take me. I looked into his eyes and told him I wanted the third. That one took longer to get to the base and we needed a lot of lube, but Jack held my gaze in his beautiful eyes and kissed me with every motion of pressure. I wanted him so badly and was rock solid in his arms.
By the time we finished our anal toys for beginners and it came to take Jack, I was ready for him. It wasn’t painful at all, and I loved having him in me. He was gentle but firm and we tried various positions, going for hours. I’d never felt so connected with anyone before. Finally, we both came together. It was so intense and magical. Holding me in his strong tattooed arms, he kissed my neck. He told me that was the best birthday present he’d ever had before whispering those three words for the first time. I’m in love.
The end!
Jack is not his real name, but his size and the rest was!
With love from team esmale
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