[M]y best friend’s Wi[F]e gave me an unforgettable experience (long) – UPDATE

A while back, I wrote about how my best friend Liam shared his wife Ally with me and she gave me an amazing, slow edging handjob. That has and always will be my most memorable orgasm where I shot the largest load of my life. The taboo nature of the entire ordeal will forever be etched in my memory as I had always lived a very straight up life. That 2 week period was almost a dream as not long after, I ended up moving back to my hometown. Here is a link to the original story:

[https://www.reddit.com/r/gonewildstories/comments/mp9vl8/my_best_friends_wife_gave_me_an_unforgettable/](https://www.reddit.com/r/gonewildstories/comments/mp9vl8/my_best_friends_wife_gave_me_an_unforgettable/)

As this is a follow up post, something obviously happened again and just as the original post, I have written a good amount of buildup picking up where the last story left off.

A few years went by and I have been in and out of the dating scene, with only one serious relationship that lasted a year. I’ve had a decent amount of sex (by my already low standards) but none of the women I’ve been seeing in the online dating scene particularly stuck out. At this stage, I’m starting to get the reality check that I may be the problem. The arrow of life however has no interest in any of that and continues its inevitable forward march through the motions.

Throughout the years, I’ve still kept a close contact with Liam and Ally. Our group chat was occasionally active with news of our fellow classmates and people we used to hang out with. Due to the covid situation, I had not gone to visit them in recent years but we did catch up when they came back to visit Liam’s family. Overall, we were still very close and I do consider Liam to be my best friend. Throughout our chats, sometimes there was still the occasional reference to the handjob that I received so many years ago. Mostly they were brought up light-heartedly during the occasional teasing I would get when talking about my love life.

Last November, Ally informed that she would be taking a business trip to the city which was about an hour away from me. She had just got into a new job and would be travelling the country’s major cities occasionally. She asked if I would be free to catch up for a coffee and I said I would be down. It was just a catch up between old friends after work. We chatted quite a bit about her new job, about how I was doing and quite a bit about Liam too although I already knew most about Liam as the group chat was essentially a conversation between us both with Ally occasionally chiming in. It was good to catch as this allowed the conversation to be focused more on her life and ideals. She looked really mature in her business attire and again felt really happy for Liam although it did make me wish for a caring and easy-going long term partner to settle down with.

She asked how I was doing and I shrugged with the usual response of mundanity. A boring life but a comfortable one. She asked if I was seeing anyone and I said yes, I was seeing a few but none of them were exclusive. I will never forget what Ally replied with:

**A: Any of them give you a handjob yet?**

I was caught off guard and felt my face turning red. I laughed it off and tried to act casual replying:

**Me: Not yet, but it would be difficult to top the one I got a few years ago. Not even I could do it.**

She laughed, the tone of the conversation was still quite casual and light. For some reason, it did not feel awkward like it would were it to be one during a date.

**A: Is that so? She must have been good… So when can I have a go at beating her?**

I remember looking away for and stretching back into my seat. I though carefully about my next few words but felt compelled to ask the burning question.

**Me: Whatever happened to you and Liam during that period of “experimenting”? Did you guys end up doing it with others?**

I realized suddenly that this was the first time I was speaking in private to Liam or Ally. For the last few years, my conversations with Liam had been through the group chat or when they both visited. As such, I had not broached the topic although I have to admit a certain amount of curiosity on my part.

**A: We did. And we still do but it has all been casual and with people we trust. I don’t know, it just feels quite… liberating I guess… I initially got into it for him but I guess I’m starting to enjoy it a bit more now.**

**Me: Is it only handjobs?**

**A: Yes, it’s where I feel the most comfortable and I guess I’m pretty good at it too from the feedback I’ve gotten. He likes it this way. It’s casual and innocent enough to get him through his wife-sharing obsession.**

**Me: Well, lucky me I suppose. I’ve always sort of thought this was it too and honestly it is kinda hot if you’re on board with it too.**

**A: It is exciting seeing to see a guy lose his self-control depending on where you touch them. It’s like a toy, touch the right places enough times and he becomes this bumbling mess of nerves.**

I immediately felt blood rushing to my cock. It’s amazing to think that the right words uttered by the right person could cause a similar reaction.

**A: So how about it? Would you like another?**

I could feel my heartbeat quicken now. Ally said it as casually as the waiter taking our orders. Something definitely changed in her these few years, she’s gotten a lot more confident and I guess success experimenting with new partners has played a huge part. I wasn’t sure how to respond so I said cautiously:

**Me: Err… not gonna lie, I don’t think anyone in my situation would not turn down such an offer. As long as Liam is cool with it…**

She laughed again, she has a sweet genuine laugh that always makes the people around her smile. Her nonchalance really put me at ease and I felt more playful than stressed choosing my words. Ally pulled out her phone and began typing.

**A: I’m sure to be thrilled to hear. Let’s find out, shall we?**

My phone buzzed and I saw she had sent a message to our group chat. “Hey babe, can I give *my name* another handjob? I kinda suggested it first”. I was shocked but tried to play it off. I get the vibe that Ally had just as much say if not more in their extra marital activities. The reply was almost immediate, “Sounds good, go easy on him. Although, he should already know what to expect”. I looked at Ally, she was smiling coyly and suddenly became a bit timid and embarrassed.

**A: See, that wasn’t weird was it? It’s sorted then.**

**Me: No, that was actually quite cool to see. I don’t know what I expected but then again, I already knew you guys have a special relationship.**

We spent the rest of the time talking about their relationship. I guess it always weirded me out bringing this up with both of them but getting the chance to find out from Ally privately now was great. She told me Liam would always ask her to tell the stories about her other handjobs. Overall, they had done it with around 8-10 others. Some just once when they were seeking for new partners, but others were repeats. She said they prefer doing it with people they can trust and added how being old friends really made it one they could both enjoy without the fear of worrying about the aftermath. Liam would ask her for details on how they went especially what they talked about afterwards. The compliments given by the guy after the handjob would always be what he was looking forward to and was always getting her to repeat the stories again and again. He would always say that she was too perfect just for his own enjoyment and he felt the need to share her skills. The satisfaction when hearing their compliments were wonderful for them both.

As it turned out, we needed to do a raincheck as she was due to head back tonight and had already checked out of her hotel. I felt a tiny bit of disappointment but I couldn’t frown for long knowing the expectations of Ally’s future “business trips”. I asked her what she liked the most so I could prepare for the next time and she said 90% of the experience was the intimacy of trust and that I had already solved 90% of the problem so there was nothing to worry about.

I remember very consciously telling myself to act normal and don’t smile like a creep but for some reason, my brain kept reminding myself of how forced and unnatural my current facial expression was. We chatted for a few more minutes before she had to head off to the airport. We hugged goodbye and she left just as two normal friends catching up would.

I went back had a good think about the situation the next few days. Sure, our friendship between the three of us would not be affected as long as I stayed within boundaries which I made a promise to myself never to cross. I told myself that I would respect Ally throughout our time together and never make any additional advances or request unless she brought it up first. It was a friends with minor benefits deal I suppose and I would be fine with that. I will continue to date other people and treat this as a bonus session as it comes. Having said that, I did feel a deep intimate connection with Ally after the first time and I told myself that feelings between us should never happen and I was okay with that decision.

Life went on for a while and I have a habit of getting lost in the daily grind. As time went on, the initial excitement after my catch up with Ally slowly waned and I just got about my daily routine. Our chat group never once again spoke about my next meeting with Ally. Christmas and New Year’s Day came and went, and life was a blur of unmemorable days until the welcome surprise of Ally’s next visit.

It was Monday evening two weeks ago when the message came. Ally was coming down on Thursday and would stay until Saturday after a Friday night work dinner and drinks. She asked if I was free to catch up on Saturday morning. I replied sure saying I was free but didn’t want to push for any further details about the timing of things and whether we would have enough time together as it would suck if things were rushed and we were on the clock. No further details came the next few days and I was starting to worry that things might not work after all. I had already refrained from masturbating since hearing the news on Monday to build up the anticipation. I kept calming myself not to stress as it seemed from our last meeting that Ally was very down to make it happen. Finally on Thursday evening, Ally messaged saying we could meet at her hotel for breakfast and that she had a late 2pm checkout. She had managed to get a later flight out that usual and I volunteered to drop her off at the airport to which she agreed.

Saturday morning came along and we met up for breakfast at her hotel. Ally was dressed in a semi-casual black dress which I assumed was what she wore the night before. She had her hair down and wore very light makeup. The dress did a good job displaying her smaller frame while not being too overly revealing. I thought it was great and was a very Ally thing not to stand out as she too often liked to observe rather than be observed. We spoke as we ate and the conversational tone felt normal but this time, I felt a hint of lingering awkwardness. I tried my best to act normal and to follow her lead. We casually chatted about her work stuff and did not mention anything about us for a while. After a short lull, she asked:

**A: So, any plans after this?**

**Me: Are we hanging out until it’s time to take you to the airport?**

**A: Yeah sounds good, I mean… you still down to come up to the room?**

**Me: Yeah, let’s do it.**

I couldn’t think of anything better to say but wanted to show interest too so I told her:

**Me: Honestly, I’ve been waiting impatiently all week since Monday so I’ve been ready for a while. It’s just… you know, I didn’t want to overstep any boundaries in case you changed your mind.**

**A: You were my first you know. As in since Liam and I got married. It was then an eye-opening experience for me and you were one of my best too… I would love to revisit it.**

I tried to laugh casually without coming off as creepy. Inside, my heart was starting to beat faster and I felt my cock stiffen. I couldn’t believe this was going to happen again. I quickly finished my breakfast, hotel prices be damned. We headed up to her room soon after. I was already semi-hard at this point and it was starting to get uncomfortable in my pants. We got to her room and it was quite standard, king bed in the middle with a study table opposite. She excused herself to the restroom for a few minutes while I browsed around admiring the view. Ally came out soon after and I excused myself as well. Nothing like getting it on with a full bladder to ruin the experience. I came out and found Ally lying on the bed looking at her phone. I didn’t know how to proceed but thankfully she patted the opposite side and beckoned me over.

**A: Well come on, make yourself comfortable.**

I sheepishly made my way over. She scooted over slightly as I lied down towards her left. Ally was smiling with one hand propping up her cheek. Here is where my brain began to malfunction. I was conscious about how close I should get and I was careful not to touch her so I just looked and lied there like an idiot. She laughed again:

**A: Well come on then, now isn’t the time to be shy. We’ve done this before after all.**

She began reaching for my belt and started undoing it. I gave her a hand and pulled down my pants revealing my boxers.

**Me: Sorry, I did think a lot about this before and I don’t want to overstep any boundaries like touching you inappropriately… so I kinda you know just follow your lead where you are comfortable.**

**A: Well you’re in this just as much as I am so don’t stress too much over it otherwise you won’t have a good time. And I won’t have a good time either. Let’s do this together and I know you’re a gentleman and won’t be doing anything wrong.**

I nodded my head okay. Somehow that felt better and I began to ease into the bed. I removed my top as well thinking I shouldn’t get cum on it as I didn’t bring a spare. Soon I found myself just in my boxers sporting a hard tent, just a thin layer of fabric between my cock and my best friend’s wife. The whole situation was so erotic that I forgot my awkwardness and started to relax putting my hands above my head. Ally looked and giggled. She touched my thigh and it felt so wrong but so good. She motioned to my cock.

**A: Well, he’s ready to go… Let’s give him a bit more time to wake up…**

I let out a deep breath as Ally began to touch me. She was still propped up on her left hand and just touching my body and thighs with her right hand. Her touch was gentle, caring and her hands were very soft. Her natural nails were painted deep red gliding all over the fabric and along my inner thighs. She moved up towards my stomach and chest and began touching me all over, even on my arms. I was as hard as my boxers would allow me to get and straining. A wet spot appeared seeping through the fabric where my tip was. I was already starting to leak precum. I let out another sigh and Ally giggled.

**Me: Your hands are so soft and your touches feel so good.**

**A: A rare compliment? Are you getting soft, *my name*?**

I gestured to my boner and said:

**Me: Err… no…**

**A: Well let’s help him out then.**

Ally sat up and reached the waistband with both hands pulling it back. My cock sprang out in all its uncircumcised glory, my careful manscaping the night before now revealed. Ally smiled acknowledging my efforts. She continued touching around the area careful to avoid my cock for now as it jumped and danced uncontrollably.

**A: I love it when they’re covered. The reveal makes it so much hotter and teasing the head so much more fun…**

**Me: I loved when you did that. Honestly, I learnt a lot from you the last time too… Some of the things you did to me, I experienced for the first time. I tried replicating it later myself but with varying levels of success.**

I tried my best to compliment her as much as I could. I could tell by the way she smiled each time or laughed that she loved it too. Ally reached over now to her bag and brought out a small jar, she really came prepared.

**A: Just a small portable jar of coconut oil I keep handy for my travels.**

She popped it open and applied a generous amount to my cock and balls. Her touch felt amazing and the slick oil made her fingers glide over it reducing the friction. I was almost fully hard now and my foreskin had peeled back revealing half of the head. Ally now started her massaging my shaft. She used all ten fingers squeezing and releasing at various points. It felt so good and relaxing to my pent-up cock and I could feel more blood rushing into it. She had a special technique where she rolled her fingers together in an almost pinching motion going not just up and down but left and right as well. This really loosens my foreskin making it glide more freely around. Ally continued with this for a while as my cock grew fully hard in her hands. I must say that she has really perfected the handjob grip. The only way I could describe it is that it is always lighter than what gets you going. This makes the buildup way slower and unrushed resulting in a more intense climax. Pair that with her experience of reading cues and knowing when to back off really makes for a special experience.

Ally spent a while massaging my shaft far away from my sensitive ridge and head. I relaxed into the sheets. This stimulation while feeling amazing, did not do much to build my arousal. Carefully, she moved her stimulation to my balls careful to cup them, massaging it in her palm while her other hands massaged the base of my shaft. This was followed by lightly grazing her fingers from the balls and up the shaft. She did this with both hands using her fingertips on the way down and her fingernails on the way up. Although the pressure Ally used was still really light, the downward motion with the fingertips had slightly more pressure resulting in my foreskin slowly creeping down lower and lower exposing my bare head. I was fully hard already despite barely any regular up and down motion yet.

**A: Are you alright? You’ve been rather quiet.**

**Me: Just trying to savor the moment. Did I said you were good? You know just when to back off and your grip is just soft enough that it keeps the arousal building while making me yearn for more pressure.**

I was sure to let the compliments flow as I could see her face swell with pride but not quite sure how to display it. She looked really cute trying to suppress it.

**A: Shall I increase the pressure then? How about giving the sensitive areas some more attention?**

She formed her now familiar ring with her thumb and index finger. While I wasn’t particularly girthy, her small fingers were small enough that the ring fit almost perfectly around my shaft. There was a bit more pressure now as she glided the ring down to my base starting just below the ridge. Once at the base, she would return to the top and once again come down, careful not to touch my head yet. After a few rounds, my foreskin was now fully peeled back. My cockhead red and throbbing, awaiting her touch.

Reaching for more oil, Ally now pinched some out with the same two fingers rubbing it together. She sat up and with her left hand holding my base and foreskin in place, formed the ring with her oil covered fingers and placed it around the base of my shaft. For the first time, she started going upwards. Because she was holding it down, the ring glided up without moving the foreskin. It felt so good and her slow speed and soft touch amplified the feeling tenfold. The ring crept its way up until it inevitably bumped against the ridge at the base of my head. I twitched involuntarily and drew a sharp breath. It felt wonderful. The tease of first having this sensitive area covered, then slowly exposed and now finally touched was very arousing. Ally’s ring made its way carefully around the ridge and over closing over my glans and tip. Then the ring repeated, starting from the base again going up but only this time it started a little higher. She would repeat this move but every time, start a little higher than before. Each stroke was also taking less and less time to get to the tip. For a while, I basked in the sensations as the stimulated area inevitably became smaller and smaller focusing around the tip.

Finally, the last few ring strokes started just below the ridge and only stimulated my glans. It was a glorious feeling. The oil ensured the friction was minimal. At this stage, I felt an overwhelming urge to thrust my hips. However, I fought hard against my instincts and tried my hardest to relax and let Ally drive the experience. It was an unbelievably erotic experience to relinquish control and instead try to hang on. My thoughts only driving my arousal higher and higher and I felt the cum building.

As if she could read my mind, Ally slowed the pace further and eventually stopped stimulating the glans altogether. She returned to the just massaging the shaft with her fingertips again and fondling the balls. I once again returned to a relaxed state all too happy to let Ally decide what to do. Her cute laugh returned:

**A: Were you getting too excited just now?**

**Me: Yeah, I think you know it’s sensitive at the top. But in a good way. You seem to know how and when to push the right buttons.**

**A: Mmmm, guess it’s usually the same with most guys. I find the ones that just relax and don’t try to steer the experience towards a more familiar grip tend to enjoy it the most.**

**Me: I’m trying my best to relax now but yeah it was hard not to thrust when you were just playing with the head.**

**A: You’re doing well… Ready for a bit more?**

I nodded letting a long breath out. Ally continued massaging the shaft for a while with her fingertips, her red nails on full display. Slowly, her fingertips made its way up to the exposed head, massaging it gently. All 10 fingers finding a spot on my glans going around in light circles. Her thumbs made its way to the frenulum behind the head, continuing to massage it all around. Now, she moved one more hand gripping the base again while her fingers from the other hand squeezed and danced on the head. She would move it in all kinds of ways. Starting with all five fingertips at the tip, sliding them all down simultaneously towards ridge before going back up. Occasionally, she would barely graze my exposed crown with her fingernails which felt delightful. At other times, her index and middle finger formed a “V” and she would slide it back and forth just stimulating the ridge. The “V” would also close from the ridge to the tip before coming back down. Next, Ally would rest her four fingers on the glans while her thumb drew light circles on my frenulum. She would use just enough pressure on the frenulum so the band moved with her finger going in circles and then reversing direction. All this while her other hand gripped the base not just keeping the foreskin back but also keeping the blood in the head turning it a dark red.

In all my solo experiences, I found it was nearly impossible to replicate these sensations. Firstly, it would require a huge amount of patience and self-control which I regrettably do not possess but more importantly, it would also be difficult to maintain full erection with such minimal and focused stimulation. With Ally however, I was having no such trouble. Despite her soft and deliberate movements, my cock was still pointing straight up, squirming and pulsing as if it had a mind of its own.

Having slowly increased my head stimulation, Ally was now ready to begin abusing it. She cupped her palm and swirled it around my glans careful to keep the pressure very light. My hips began bucking as my breath grew erratic. She looked at me and asked gently:

**A: Just let me know if it’s too sensitive. We can switch back to something more normal.**

Her gentle and caring nature added so much more to the experience. I could only nod my head at this point, my every muscle screaming to move away from her palm. It took a lot of effort, but I did my best to fight through the sensitivity and bear the over-stimulation. She stopped after a few circles to let me calm down, massaging my shaft and balls again. I caught my breath and managed to say:

**Me: Wow, that was intense… I could never do that to myself willingly but somehow feels so hot when you are doing it….**

**A: Do you like it then? Does it feel good?**

**Me: As long as you are touching it, I will like it…. It’s different with you…**

**A: Are you ready to go again?**

She carefully returned to palming my glans and the sensitivity returned but somehow with less intensity this time. I could definitely feel the pleasure more this time. After a few more breaks, the palming was actually starting to feel good. I felt my orgasm starting to build but very very slowly. Just as I was getting used to this type of stimulation, she stopped again, this time letting go completely. She moved her hands along my thighs and chest again as my now out-of-control cock jumped and twitched on its own. Ally seemed to be slightly amused but said nothing.

Before my arousal could subside, she resumed her touches. Now with both hands, she started going only down from the head to the base. One after another, both her hands with a full grip but once again never too tight. Occasionally, she would throw in an upstroke which would feel exquisite. Her knowledge of knowing just which stroke to focus on and when to throw in another was impeccable. Still on her downward only alternating strokes, she suddenly stopped mid-stroke with one hand at the base. Instead of removing it, she kept it there just as she had before holding my foreskin in place. She made a slow movement with her free hand carefully wrapping it fully engulfing my head. She squeezed it and released a few times, not moving up or down. Slowly her squeezing imperceptibly evolved into twisting and then into very slight up and down motions. This was another all out attack on the sensitive head, squeezing, twisting and stroking it with a more medium grip this time.

Because my head had already received so much stimulation, this was now just pure pleasure. Despite still being extremely sensitive, all Ally’s previous stimulation now made it bearable and my body was able to reap the rewards. The concentration of nerve endings around my cockhead was being triggered all at the same time and was returning nothing but wave after wave of pure, insensitive joy without getting over-stimulated. I was building towards orgasm and fast. In the midst of this, I managed to blurt out:

**Me: Holy shit! I think I’m getting close… Oh my god…**

My breath stuttered multiple times as my body writhed in Ally’s hands. I remember very clearly that she reduced her grip further and slowed down the pace of the squeezing. I felt every ridge between her fingers as it brushed up and down my flared cockhead. It was too late to bring down my arousal any further to prolong the edging but her changed grip managed to delay it, prolonging my inevitable climax. My point of no return stretched as I told my body not to tense and just try to relax.

**A: I can feel it coming, *my name*… Don’t fight it… Just let go… And you will feel good…**

I could not muster a reply, just nodded my head. I was clawing at the sheets now, my hands once above my head now roamed aimlessly at my side. I remember the direct glans stimulation was building my orgasm to new heights. I remember basking in a state of near-orgasm for a very long time, longer than I ever felt before as the moment to moment feeling on the edge reached ever greater heights of arousal. The feeling of climbing the final peak before orgasm was almost as good as the orgasm itself. The point of no return hit way before that as I could still remember consciously telling my body to relax. Usually, I would not have time to think but somehow it stretched on for so long that I was acutely aware of every moment. At the peak, my cock tensed as all my lower body muscles clenched. Then the muscles involuntarily released and with it an eruption of cum. Clear droplets sprayed first all over my body and the bed as my cock pulsed in Ally’s hand. She kept it slightly angled towards me, constantly massaging the head as the first thick white jet flew and hit the headboard with a thud, followed by another three more shots over my left shoulder while the rest completely shot all across my chest and stomach. The remaining came down over Ally’s hands and red nails. I was still oozing after what must have been over the twentieth orgasm pulse. My cock twitched another few more times without any more cum.

I was breathing hard throughout and as the emotions slowly overcame me, those breaths turned to laughter. Ally was laughing next to me too, her hands still holding my cock and gently stroking until the last drop came out. She stopped when she was sure it was over and put her hands on my chest as she came to lay next to me. I put an arm around her, my previous fear of getting too close or touching completely forgotten. We lay in silence for a while until she said:

**A: Well, have you gotten over it yet? How was it?**

**Me: Words can’t do justice to what I just felt. The final stretch just went on for so long and felt so good. It was like climbing the highest water slide knowing what awaits me on the other side. Not only that, every moment felt more amplified and stretched out, like time was moving slower. I could savor the pleasure more intensely than usual.**

Ally smiled gleefully hearing those words. Again she had the funny expression when being complemented.

**A: Did I do enough to get the top spot?**

**Me: Nope, but you’re welcome to try again.**

I eyed her playfully, knowing she would pick up on my sarcasm. She nudged me with her head annoyingly as her cum-stained hands were still on my chest. We laid together for a long time. I explained to her in greater detail what I felt at various moments and was sure to praise her along the way. We got cleaned up, showered and then it was time for lunch.

I took her to the airport later and we said our goodbyes, but not before she brought up catching up again the next time she was over. I was careful not to push for more details but our earlier conversations hinted that it could be months later. One certainty was that she would at some point make another trip. Ally disappeared into the airport and left me alone to ponder over what just happened. Pretty soon after, life for me returned to normal and everything that took place felt like a distant fantasy but one I would revisit many times for the rest of my life.

Source: reddit.com/r/gonewildstories/comments/smp5qp/my_best_friends_wife_gave_me_an_unforgettable