Jess surpassed herself the other night by enjoying not one, but two gentlemen within hours of each other.
As a reminder Jess [22F] and I, Oliver, [26M] have been together nearly 4 years and have explored our wild side extensively hand in hand.
On the night in question, there was an awards ceremony for a society Jess is a member of, and one I used to be a member of previously. That night in particular I was in London on business.
In the days leading up to the event Jess had been particularly flirty with a mutual friend of ours, one whom we have had a threesome with previously. But had recently been in a committed relationship until they broke up three weeks prior.
With our friend Christian now single, he had made a few subtle comments and hints to Jess, such as “it must be time for round 2.” At my encouragement Jess had sent a few riské pics and further referenced our threesome with him over the past couple of weeks. Alas the opportunity for physical satisfaction had yet to come about.
Back to the night in question at the award ceremony, Jess wore a stunning blue dress I had bought her that showed off her stunning figure (heads up, she’s been on a major fitness drive and she looks sublime). She paired this with an equally gorgeous matching set of floral underwear and a set of coral high heels. All in all, quite classy.
I had teased her earlier that day about the possibility of her being ‘loaned’ out of the evening/night, and once there Jess let me know that Christian had said he would like her pants in his pocket by the end of the night. She retreated to the bathroom and did the deed, sending me a quick text that she was doing so. Next thing I know I got a text from him:
“I might have Jess’ pants in my pockets.”
I told him he could use Jess as he please.
Then I didn’t hear anything for a while until Jess alerted me that another mutual friend, Andrew, had joined their conversation. Now Andrew, or Andy, is mentioned in another story we posted on here. Essentially he was Jess’ neighbour who she fucked a few times over the past 18 months. He’s a good friend and is now currently in a relationship. However, Jess let me know that both Christian and Andy were aware she was pantless.
Cue me asking for a picture of this fine ensemble.
They scurry off to the stairwell and I receive a rather artistic photo of my girlfriend with her dress being lifted by Christian and Andy with no underwear on. She later informed me she was dripping wet by this point.
I quickly text Christian that he had free reign to use Jess as he wished, and that she was clean and on the pill. Andy, as mentioned, was in a relationship but a complicated one at that. Nevertheless I was very hesitant about Jess having a threesome without me there, particularly one ripe for potential fall out. Andy ducked out and Christian and Jess order an uber to hers.
Next thing I hear is that Jess is in an uber with Christian on their way to her house. As she tells it they rushed up to her room before she undressed him and took his cock into her mouth. Now I know for a fact that Jess is unbelievable at blowjobs, so I was not surprised when Christian said Jess was far better than his recent ex.
The next photo I received was Jess in nothing but bra and her high heels kneeling on the bed. Christian had requested she keep the shoes on and proceeded to eat her out before bringing our riding crop to bare.
Now Jess and I have accumulated an impressive stash of sex toys and accessories over the years, so I was pleased they were being put to good use. Christian had Jess whipped and fucked with various toys and vibratory. One video had her naked body spread on the bed with her tits and legs being whipped and a magic wand strapped to her pussy. Jess sent me a voice note of her cumming which was insanely hot, crying out his name as he fucked her with the toys, driving her over the edge. Christian proceeded to use the toys on Jess over and over again until she came multiple tines, all the while sending me incredible videos of her naked body writhing under him.
Unfortunately at this stage it seemed whisky got the better of Christian and he couldn’t quite keep the colonel up to claim his just reward.
After a swift exit Jess was left wanting more. However, her usual standby guy, Andy, was in a relationship and despite his reservations about his current situation was essentially unavailable.
So when Jess’ housemates came home from same the awards ceremony we assumed that was the end of that.
It wasn’t until Jess informed me she was in her housemate Tom’s room in just a dressing gown, that I thought the night could be salvaged.
Now Tom is also another recent singleton, and was a new arrival to Jess’ dirty thoughts. I gave Jess a very simple challenge, she had 20 minutes to suck his cock, and I left her to it.
20 minutes later Jess tells me she hasn’t yet but it could happen soon. Tom had closed the door of his room and dimmed the lights. 5 minutes later I get the text:
“I have his cock in my mouth”
I proceeded to receive a photo and video of Jess sucking Tom’s cock, and not to my surprise Tom told me Jess was far superior to his ex.
Jess told me he grabbed her hair and throat and drove his cock deep in her mouth and shot his cum instead her. Like the good girl Jess is, she swallowed as always.
Unfortunately, Tom was unable to raise the troops again, so Jess left it there and came back to facetime me… After enjoying two men that evening.
N.B: I can’t upload any images as they contain identifying features or faces. I may upload the text conversation once I figure out an easy way to censor the text.
Source: reddit.com/r/gonewildstories/comments/doh7t0/jess_got_into_double_trouble_mf_x2
Glad to see you back posting again!