Older Woman Continued - Something of a Threesome With Her Friend

I was at Jill’s house with her girlfriend Shirley.  We were in the hot-tub drinking wine.  Shirley was about Jill’s age, married, and somewhat overweight.

Jill and Shirley were telling me about their “Girls Trip” to the Caribbean.  During the trip they had a masseuse come to their villa.  They said the man was young and very handsome.  The girls debated if the masseuse would have “wanted to do more.”

They also told me when sunning by the pool on their trip, they both lowered their tops to get an overall tan.  I told the girls that I wish I was there, so I could have seen them topless.  Shirley said, “You’ve seen Jill’s boobs.”  I replied back, “But not yours.”

With some more wine and more talking, I convinced Shirley to flash me.  Shirley lowered the strap on her swimsuit, exposing one breast.  She covered up again quickly.  I told Shirley I missed it because I blinked my eyes.  With more talking and wine, soon both girls lowered the tops to their swimsuits.

Shirley told Jill how lucky she was to have a handsome young guy (me) giving her massages and attending to her 'other needs'.  Shirley said her husband was 'old fashioned' and believed oral sex was dirty.  She told us her husband said, “Only a whore would perform oral sex on a man.”  Shirley also said she had never been eaten.  I volunteered to perform oral sex on Shirley.

At first, both girls were taken aback.  I suggested I could give Shirley a massage, and then go just a little further.  We were drinking.  At first, we were joking as we talked.  Then the conversation became serious.

We set up the rules.  I would give Shirley a massage with just me and her in one of the bedrooms.  All the time I was in the room with Shirley, I had to keep my swimsuit and a T-Shirt on.  Shirley could stop anytime she wanted.

Shirley went into a bedroom to get ready.  I dried my swimsuit off, and put on a T-Shirt.  When I got in the room, Shirley was lying on her stomach naked, covered with a towel.  My girlfriend Jill stayed out of the room.

I started by massaging Shirley’s back and shoulders, keeping her ass covered with the towel.  I kept her ass covered as I massaged her legs, with a lot of attention given to her feet.

I turned Shirley over to lie on her back.  I covered her breasts and pussy with the towel.  Keeping Shirley covered, I massaged her neck and shoulders.

I went to Shirley’s legs and feet, keeping her breasts and pussy covered.  I went back up to her shoulders and lowered the towel exposing her breasts, still keeping her pussy covered.  I massage her breasts and licked her nipples.

My hand moved under the towel to her pussy.  Shirley was wet.  Using her wetness as a lubricant I massaged her inner and outer lips and all around her clit, without touching her clit.  I took the towel completely off her body.  All the while, I was kissing her nipples.

I put my fingers inside her wet pussy.  Then I massaged around her clit and on her clit.  As I was kissing my way down her body, I stopped touching her pussy.  When I got to her pussy, I teased her by ignoring it.  I kissed down her leg until about her knee.  Then I started kissing up the inside of her thighs towards her pussy.  When my mouth got to her pussy, I started licking up and down her slit, trying to put my tongue inside.

I licked her clit and all around and in-between her inner lips.  I started tickling her asshole.

My girlfriend Jill was outside the bedroom.  She later told me she could hear her friend Shirley moaning in delight.  Shirley’s body was shaking, and she was running her hands through my hair as I am eating her to an orgasm.

Shirley had enough and asked me to stop.  I gently rubbed her body as she was calming down.

Shirley and I hugged in bed.  Shirley put on her swimsuit and the both of us left the room.

Jill, Shirley, and I went back into the hot-tub with our swimming suites on.

Talking in the hot-tub, Shirley asked me if there was anything I wanted.  I told her a two-girl blowjob.  Jill looked at Shirley and both girls nodded in agreement.  Jill & Shirley again lowered their tops.  Sitting in the hot-tub, I slid off my swimsuit.  Under the water, both girls grabbed my cock.

I sat on the edge of the tub.  First Jill sucked me, and then Shirley.  The girls took turns with my dick in their mouths as I was playing with their tits.  When I told them I was ready to cum, Shirley let Jill finish me.  Shirley gave my dick one more kiss before I slid back into the water.

I got back into the water naked.  Jill and Shirley did not pull the tops of their swimsuits back up.  I was hard again.  I moved the girls’ hands so they could feel my hard-on.  Jill told me I had already received my blowjob.  I kept putting the girls’ hands on my cock.  The three of us jacked me off while I was sitting in the hot-tub.

That was my only experience with Shirley.  Later, the three of us talked.  Shirley said she was drunk, and we should never mention our experience.  Jill, Shirley, and I kept quiet.

I met Shirley and her husband a few times.  When meeting Shirley’s husband, all I could think was, “What a dummy.  He thinks if his wife sucked his cock, she would be acting like a whore.  However, his frustrated wife did act like a whore with me.”