diff --git a/.verb.md b/.verb.md
index b49d5cf..12d8c23 100644
--- a/.verb.md
+++ b/.verb.md
@@ -118,7 +118,7 @@ The following options may be used with the main `picomatch()` function or any of
 | [onMatch](#optionsonMatch) | `function` | `undefined` | Function to be called on matched items. |
 | [onResult](#optionsonResult) | `function` | `undefined` | Function to be called on all items, regardless of whether or not they are matched or ignored. |
 | `posix`               | `boolean`      | `false`     | Support POSIX character classes ("posix brackets"). |
-| `prepend`             | `boolean`      | `undefined` | String to prepend to the generated regex used for matching. |
+| `prepend`             | `string`       | `undefined` | String to prepend to the generated regex used for matching. |
 | `regex`               | `boolean`      | `false`     | Use regular expression rules for `+` (instead of matching literal `+`), and for stars that follow closing parentheses or brackets (as in `)*` and `]*`). |
 | `strictBrackets`      | `boolean`      | `undefined` | Throw an error if brackets, braces, or parens are imbalanced. |
 | `strictSlashes`       | `boolean`      | `undefined` | When true, picomatch won't match trailing slashes with single stars. |
diff --git a/README.md b/README.md
index 158a8ba..31b8b56 100644
--- a/README.md
+++ b/README.md
@@ -351,7 +351,7 @@ The following options may be used with the main `picomatch()` function or any of
 | [onMatch](#optionsonMatch) | `function` | `undefined` | Function to be called on matched items. |
 | [onResult](#optionsonResult) | `function` | `undefined` | Function to be called on all items, regardless of whether or not they are matched or ignored. |
 | `posix`               | `boolean`      | `false`     | Support POSIX character classes ("posix brackets"). |
-| `prepend`             | `boolean`      | `undefined` | String to prepend to the generated regex used for matching. |
+| `prepend`             | `string`       | `undefined` | String to prepend to the generated regex used for matching. |
 | `regex`               | `boolean`      | `false`     | Use regular expression rules for `+` (instead of matching literal `+`), and for stars that follow closing parentheses or brackets (as in `)*` and `]*`). |
 | `strictBrackets`      | `boolean`      | `undefined` | Throw an error if brackets, braces, or parens are imbalanced. |
 | `strictSlashes`       | `boolean`      | `undefined` | When true, picomatch won't match trailing slashes with single stars. |
diff --git a/lib/parse.js b/lib/parse.js
index 0bb4116..87c84a7 100644
--- a/lib/parse.js
+++ b/lib/parse.js
@@ -415,7 +415,7 @@ const parse = (input, options) => {
     start: 0,
     dot: opts.dot === true,
     consumed: '',
-    output: '',
+    output: bos.output,
     prefix: '',
     backtrack: false,
     negated: false,
@@ -585,7 +585,8 @@ const parse = (input, options) => {
         // Suitable patterns: `/!(*.d).ts`, `/!(*.d).{ts,tsx}`, `**/!(*-dbg).@(js)`.
         //
         // Disabling the `fastpaths` option due to a problem with parsing strings as `.ts` in the pattern like `**/!(*.d).ts`.
-        const expression = parse(rest, { ...options, fastpaths: false }).output;
+        // Clear prepend so the suffix is not prefixed again; the outer bos token already holds it.
+        const expression = parse(rest, { ...options, fastpaths: false, prepend: '' }).output;
 
         output = token.close = `)${expression})${extglobStar})`;
       }
@@ -603,7 +604,8 @@ const parse = (input, options) => {
    * Fast paths
    */
 
-  if (opts.fastpaths !== false && !/(^[*!]|[/()[\]{}"])/.test(input)) {
+  // Fast paths skip tokenization, which is where options.prepend is applied.
+  if (opts.fastpaths !== false && !opts.prepend && !/(^[*!]|[/()[\]{}"])/.test(input)) {
     let backslashes = false;
 
     let output = input.replace(REGEX_SPECIAL_CHARS_BACKREF, (m, esc, chars, first, rest, index) => {
diff --git a/lib/picomatch.js b/lib/picomatch.js
index 9c2bfd5..091a12a 100644
--- a/lib/picomatch.js
+++ b/lib/picomatch.js
@@ -309,7 +309,8 @@ picomatch.makeRe = (input, options = {}, returnOutput = false, returnState = fal
 
   let parsed = { negated: false, fastpaths: true };
 
-  if (options.fastpaths !== false && (input[0] === '.' || input[0] === '*')) {
+  // Fast paths skip tokenization, which is where options.prepend is applied.
+  if (options.fastpaths !== false && !options.prepend && (input[0] === '.' || input[0] === '*')) {
     parsed.output = parse.fastpaths(input, options);
   }
 
diff --git a/test/options.prepend.js b/test/options.prepend.js
new file mode 100644
index 0000000..18a631e
--- /dev/null
+++ b/test/options.prepend.js
@@ -0,0 +1,40 @@
+'use strict';
+
+const assert = require('assert');
+const { isMatch, makeRe, parse } = require('..');
+
+describe('options.prepend', () => {
+  it('should prepend a string to the parsed regex source (issue #110)', () => {
+    const state = parse('abc', { prepend: 'foo' });
+    assert.strictEqual(state.tokens[0].output, 'foo');
+    assert.strictEqual(state.output, 'fooabc');
+  });
+
+  it('should prepend a string to the generated matcher regex', () => {
+    assert.strictEqual(makeRe('abc', { prepend: 'foo' }).source, '^(?:fooabc)$');
+    assert(isMatch('fooabc', 'ab*', { prepend: 'foo' }));
+    assert(!isMatch('abc', 'ab*', { prepend: 'foo' }));
+  });
+
+  it('should prepend a string when compiling common fast-path patterns', () => {
+    const re = makeRe('*.js', { prepend: 'foo' });
+    assert.ok(re.source.indexOf('^(?:foo') === 0);
+    assert(isMatch('fooa.js', '*.js', { prepend: 'foo' }));
+    assert(!isMatch('a.js', '*.js', { prepend: 'foo' }));
+  });
+
+  it('should not double-prepend when the parser rebuilds output after backtracking', () => {
+    const re = makeRe('[[:alpha:]]', { prepend: 'foo' });
+    assert.ok(re.source.indexOf('^(?:foo') === 0);
+    assert.strictEqual(re.source.split('foo').length - 1, 1);
+    assert(isMatch('fooa', '[[:alpha:]]', { prepend: 'foo' }));
+    assert(!isMatch('a', '[[:alpha:]]', { prepend: 'foo' }));
+  });
+
+  it('should not re-apply prepend when parsing a suffix after a negated extglob', () => {
+    const state = parse('!(*.d).ts', { prepend: 'foo' });
+    assert.strictEqual(state.output.split('foo').length - 1, 1);
+    assert(isMatch('foofile.ts', '!(*.d).ts', { prepend: 'foo' }));
+    assert(!isMatch('foofile.d.ts', '!(*.d).ts', { prepend: 'foo' }));
+  });
+});