That’s how our next few sessions went as well. We’d meet in his hotel room after he was done with work, maybe have a drink or two while complaining about our respective days, and then Sam would force orgasm after orgasm out of me with a new clit toy of the month before making me suck his cock or give him a thighjob. It’s weird to think back on all the stuff we did without outright penetration – Sam pressing me into walls, his cock furiously rubbing between my pussy folds as he fucked my legs and groped my breasts; taking a shower together, which ended with me deep throating him for the first time and choking on his come; him laying down on the bed and me sliding my pussy over and over his cockhead until he came. We’d both decided to stop using condoms at that point since we’d gotten tested. This was rapidly becoming all too comfortable, even though I was still feeling guilty over helping Sam cheat and then guilty over liking the sex with him so much. He’d indulged my fantasy while introducing me to new ones: sensory deprivation, 69-ing, exhibitionism (sucking him off by the glass balcony door), and daddy-daughter role playing.
“Would you ever consider going further?” Sam asked after a particularly great meetup, when he’d worked me over with the Hitachi and then taken me doggystyle on the hotel couch.
“What do you mean?” I asked.
Sam slipped his fingers between my legs and curled them right at my entrance. Right where my intact hymen was, the only thing he still hadn’t had.
“You can’t penetrate me,” I said firmly. “I can’t risk getting pregnant. And. It would hurt, which I’m not into.”
Sam nodded. “What about with a toy? A really good one, to make it worth your while?”
This I had to think about. A couple months ago, I would’ve said no way immediately. However, I’d recently learned that my parents were divorcing, which is a huge deal in my childhood community, and it made me question more than ever whether I actually wanted to “wait for marriage.” Plus, I knew Sam would make my first time good, even if he was using a toy instead of his cock.
“I guess it would depend on the toy,” I whispered into Sam’s neck, and then got distracted when he started using the Hitachi on my clit again.
*
I resisted the idea of giving up my virginity for several more months, but Sam, being the patient sort of man, slowly wore me down. He’d bring it up just as I was about to come, my pussy clenching and weeping juices from how empty it was. He would fuck between my thighs and whisper filthy things about how tight and hot I was around his cock, how good it felt to push in and cum over my virgin walls. And he’d send me videos of women having G-spot orgasms, adding that he’d hate for me to miss out on such an experience.
“Oh god, fine,” I finally relented, a week after graduation and moving into my first “adult” apartment with my first full-time job paycheck. “Okay, let’s do it.”
I assumed that we would use a toy like the Rabbit or another kind vibrating dildo. Even though I knew my first time (?) would be uncomfortable, Sam had become so adept at training my body to come for him (seriously, I’d come several times from thigh-fucking alone because of his ministrations) that I was excited regardless. However, he had a special thing in store for my first time. He had a Sybian.
Source: reddit.com/r/gonewildstories/comments/7ogah2/my_f_forced_orgasm_experience_with_a_married_man
Can’t wait for part 5